Spectroscopic analysis of vibronic relaxation pathways in molecular spin qubit [Ho(W5O18)2]9−: sparse spectra are key

Molecular vibrations play a key role in magnetic relaxation processes of molecular spin qubits as they couple to spin states, leading to the loss of quantum information. Direct experimental determination of vibronic coupling is crucial to understand and control the spin dynamics of these nano-objects, which represent the limit of miniaturization for quantum devices. Herein, we measure the vibrational properties of the molecular spin qubit $[$Ho(W$_5$O$_{18}$)$_2]^{9-}$ by means of magneto-infrared spectroscopy. Our results allow us to unravel the vibrational decoherence pathways in combination with $ab$ $initio$ calculations including vibronic coupling. We observe field-induced spectral cha…

Unveiling the nature of supramolecular crown ether–C60 interactions

A series of exTTF-(crown ether)2 receptors, designed to host C60, has been prepared. The size of the crown ether and the nature of the heteroatoms have been systematically changed to fine tune the association constants, which were determined by a number of complementary spectroscopic techniques. Electrochemical measurements and transient absorption spectroscopy assisted in corroborating charge transfer in the ground state and in the excited state, leading to the formation of radical ion pairs featuring lifetimes in the range from 12 to 21 ps. To rationalize the nature of the exTTF-(crown ether)2$C60 stabilizing interactions, theoretical calculations have been carried out, suggesting a syner…

Improving the Robustness of Organic Semiconductors through Hydrogen Bonding

Molecular organization plays an essential role in organic semiconductors since it determines the extent of intermolecular interactions that govern the charge transport present in all electronic applications. The benefits of hydrogen bond-directed self-assembly on charge transport properties are demonstrated by comparing two analogous pyrrole-based, fused heptacyclic molecules. The rationally designed synthesis of these materials allows for inducing or preventing hydrogen bonding. Strategically located hydrogen bond donor and acceptor sites control the solid-state arrangement, favoring the supramolecular expansion of the π-conjugated surface and the subsequent π-stacking as proved by X-ray d…

Relationship between Electron Affinity and Half-Wave Reduction Potential: A Theoretical Study on Cyclic Electron-Acceptor Compounds.

A high-level ab initio protocol to compute accurate electron affinities and half-wave reduction potentials is presented and applied for a series of electron-acceptor compounds with potential interest in organic electronics and redox flow batteries. The comprehensive comparison between the theoretical and experimental electron affinities not only proves the reliability of the theoretical G3(MP2) approach employed but also calls into question certain experimental measurements, which need to be revised. By using the thermodynamic cycle for the one-electron attachment reaction A+e- →A- , theoretical estimates for the first half-wave reduction potential have been computed along the series of ele…

Frontispiece: Hierarchy of Asymmetry at Work: Chain-Dependent Helix-to-Helix Interactions in Supramolecular Polymers

Neutral and oxidized triisopropylsilyl end-capped oligothienoacenes: a combined electrochemical, spectroscopic, and theoretical study.

This work presents an analy- sis of the structural, electrochemical, and optical properties of a family of triisopropylsilyl end-capped oligothie- noacenes (TIPS-Tn-TIPS, n = 4-8) by combining cyclic voltammetry, spectro- scopic techniques, and quantum-chemi- cal calculations. TIPS-Tn-TIPS com- pounds form stable radical cations, and dications are only obtained for the lon- gest oligomers (n = 7 and 8). Oxidation leads to the quinoidization of the con- jugated backbone, from which elec- trons are mainly extracted. The absorp- tion and fluorescence spectra show par- tially resolved vibronic structures even at room temperature, due to the rigid molecular geometry. Two well-resolved vibronic p…

Enhanced electronic communication through a conjugated bridge in a porphyrin-fullerene donor-acceptor couple

A ZnP-2EDOTV-C60 triad, with enhanced electronic communication between terminus donor and acceptor moieties, was synthesized and studied both experimentally and theoretically. Electrochemical measurements and density functional theory calculations support that the first oxidation takes place on the 3,4-ethylenedioxythiophenevinylene (2EDOTV) bridge followed by the oxidation of the ZnP moiety at slightly higher energies. The electronic communication between the terminal electron-donor ZnP and the electron-acceptor C60 units is enhanced by the conjugated EDOTV-based spacer leading to photoinduced electron transfer over the distance >2 nm in the picosecond time domain. The involvement of the s…

Helical supramolecular polymerization of C3-symmetric amides and retroamides: on the origin of cooperativity and handedness.

The cooperative supramolecular polymerization of 1 and 2 yields P- or M-type helical aggregates depending on the absolute configuration (S or R) of the stereogenic centres attached to the side chains. The connectivity of the amide group does not affect the handedness of the helical aggregates, but determines a larger cooperativity for retroamides 1.

Dual-Mode Chiral Self-Assembly of Cone-Shaped Subphthalocyanine Aromatics

This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of the American Chemical Society, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/jacs.0c07291

Accurate Treatment of Large Supramolecular Complexes by Double-Hybrid Density Functionals Coupled with Nonlocal van der Waals Corrections.

In this work, we present a thorough assessment of the performance of some representative double-hybrid density functionals (revPBE0-DH-NL and B2PLYP-NL) as well as their parent hybrid and GGA counterparts, in combination with the most modern version of the nonlocal (NL) van der Waals correction to describe very large weakly interacting molecular systems dominated by noncovalent interactions. Prior to the assessment, an accurate and homogeneous set of reference interaction energies was computed for the supramolecular complexes constituting the L7 and S12L data sets by using the novel, precise, and efficient DLPNO-CCSD(T) method at the complete basis set limit (CBS). The correction of the bas…

Effect of Substituents at Imide Positions on the Laser Performance of 1,7-Bay-Substituted Perylenediimide Dyes

Perylenediimide (PDI) compounds with no substituents in their core are widely used as the active units of thin-film organic lasers. Recently, bay-substituted PDIs (b-PDIs) bearing two sterically hindering diphenylphenoxy groups at the 1,7-bay positions have received great attention because they show red-shifted emission with respect to bay-unsubstituted PDIs, while maintaining high photoluminescence (PL) quantum yields and low amplified spontaneous emission (ASE) thresholds even at high doping rates. However, their ASE photostability is relatively low compared to that of state-of-the-art PDIs. Thus, the design of b-PDIs with improved ASE photostability remains a challenge. Here, the synthes…

Tetrasubstituted Thieno[3,2- b]thiophenes as Hole-Transporting Materials for Perovskite Solar Cells

Three hole-transporting materials (HTMs) were prepared following a straightforward synthetic route by cross-linking arylamine-based ligands with a simple thieno[3,2-b]thiophene (TbT) core. The novel HTMs were fully characterized with standard techniques to gain insight into their optical and electrochemical properties and were incorporated in solution-processed mesoporous (FAPbI3)0.85(MAPbBr3)0.15 perovskite-based solar cells. The similar molecular structure of the synthesized HTMs was leveraged to investigate the role that the bridging units between the conjugated TbT core and the peripheral arylamine units plays on their properties and thereby on the photovoltaic response. A remarkable po…

High-Efficiency Perovskite Solar Cells using Molecularly-Engineered, Thiophene-Rich,Hole-Transporting Materials: Influence of Alkyl Chain Length on Power Conversion Efficiency

The synthesis and characterization of a series of novel small-molecule hole-transporting materials (HTMs) based on an anthra[1,2-b:4,3-b′:5,6-b′′:8,7-b′′′]tetrathiophene (ATT) core are reported. The new compounds follow an easy synthetic route and have no need of expensive purification steps. The novel HTMs were tested in perovskite solar cells (PSCs) and power conversion efficiencies (PCE) of up to 18.1 % under 1 sun irradiation were 2 measured. This value is comparable with the 17.8 % efficiency obtained using spiroOMeTAD as a reference compound. Similarly, a significant quenching of the Photoluminescence in the first nanosecond is observed, indicative of effective hole transfer.Additiona…

Electrical two-qubit gates within a pair of clock-qubit magnetic molecules

Enhanced coherence in HoW$_{10}$ molecular spin qubits has been demonstrated by use of Clock Transitions (CTs). More recently it was shown that, while operating at the CTs, it was possible to use an electrical field to selectively address HoW$_{10}$ molecules pointing in a given direction, within a crystal that contains two kinds of identical but inversion-related molecules. Herein we theoretically explore the possibility of employing the electric field to effect entangling two-qubit quantum gates among two neighbouring CT-protected HoW$_{10}$ qubits within a diluted crystal. We estimate the thermal evolution of $T_1$, $T_2$, find that CTs are also optimal operating points from the point of…

Tuning the electronic properties and the planarity degree in the π-extended TTF series: the prominent role of heteroatoms

The main asset of small molecules for application in organic electronics lies in the tunability of their electronic properties owing to the precise control of their molecular design. Semiconducting properties in organic compounds are for instance closely linked to the molecular planarity degree, including when considering various redox states. Among those species, the π-extended TTF (exTTF: 9,10-bis(1,3-dithiol-2-ylidene)-9,10-dihydroanthracene) presents fascinating redox and structural properties, which have been extensively studied in various fields of organic electronics. Here we show that S-exTTF, a sulfur enriched π-isoelectronic dithieno analogue of pristine exTTF, synthesized through…

From linear quaterthiophene to sulflower: A comparative theoretical study

Abstract In this paper, we report a theoretical study of four types of thiophene-based oligomers showing the same number of C C double bonds and very different molecular structures. The comparative study has been performed on the basis of B3LYP/6-31G∗∗ calculations. The way the thiophene rings are linked together has a remarkable influence on the molecular and electronic properties. Linear quaterthiophene and heptathienoacene show similar aromatic structures but a loss of π-conjugation is detected for the latter due to the condensation of thiophene rings. A blue shift of the most intense electronic transition is predicted for fused heptathienoacene compared with non-fused quaterthiophene. C…

Understanding the affinity of bis-exTTF macrocyclic receptors towards fullerene recognition

A new series of fullerene receptors based on exTTF macrocycles with alkyl ether chains of increasing length is reported. The novel macrocyclic receptors are able to favourably interact with fullerene C60 through a synergistic combination of π–π, CH⋯π and n⋯π noncovalent interactions. We identify that the highest affinity towards C60 recognition is achieved for the host with the tightest fit; that is, the smallest receptor with a cavity large enough to host the buckyball inside (log Ka = 5.2 in chlorobenzene at 298 K). However, besides this expected observation, theoretical calculations evidence that the most stable self-assembling configuration corresponds for all the receptors to an outsid…

Synergy of Axial and Point Chirality to Construct Helical N -Heterotriangulene-Based Supramolecular Polymers

Isomerism effect on the photovoltaic properties of benzotrithiophene-based hole-transporting materials

Engineering of inorganic–organic lead halide perovskites for photovoltaic applications has experienced significant advances in recent years. However, the use of the relatively expensive spiro-OMeTAD as a hole-transporting material (HTM) poses a challenge due to dopant-induced degradation. Herein we introduce two new three-armed and four-armed HTMs (BTT-4 and BTT-5) based on isomeric forms of benzotrithiophene (BTT). The isomerism impact on the optical, electrochemical and photophysical properties and the photovoltaic performance is systematically investigated. Perovskite solar cells (PSCs) using BTT-4 and BTT-5 as HTMs show remarkable light-to-energy conversion efficiencies of 19.0% and 18.…

Dibenzoquinquethiophene- and Dibenzosexithiophene-Based Hole-Transporting Materials for Perovskite Solar Cells

Fused oligothiophene-based π-conjugated organic derivatives have been widely used in electronic devices. In particular, two-dimensional (2D) heteroarenes offer the possibility of broadening the scope by extending the π-conjugated framework, which endows enhanced charge transport properties due to the potential intermolecular π–π stacking. Here, the synthesis and characterization of two new small-molecule hole-transporting materials (HTMs) for perovskite solar cells (PSCs) are reported. The newly custom-made compounds are based on dibenzoquinquethiophene (DBQT) and dibenzosexithiophene (DBST) cores, which are covalently linked to triphenylamine moieties to successfully afford the four-armed …

Controlling the Host-Guest Interaction Mode through a Redox Stimulus

International audience; A proof-of-concept related to the redox-control of the binding/releasing process in a host-guest system is achieved by designing a neutral and robust Pt-based redox-active metallacage involving two extended-tetrathiafulvalene (exTTF) ligands. When neutral, the cage is able to bind a planar polyaromatic guest (coronene). Remarkably, the chemical or electrochemical oxidation of the host-guest complex leads to the reversible expulsion of the guest outside the cavity, which is assigned to a drastic change of the host-guest interaction mode, illustrating the key role of counteranions along the exchange process. The reversible process is supported by various experimental d…

Titelbild: Electron Transfer in a Supramolecular Associate of a Fullerene Fragment (Angew. Chem. 8/2014)

Supramolecular assembly of pyrene-tetrathiafulvalene hybrids on graphene: Structure-property relationships and biosensing activity

Two different molecular receptors (1 and 2) incorporating one and three pyrene units to promote the π–π interaction with the basal plane of graphene are reported. In order to modulate the electronic properties of graphene, the new receptors are endowed with an electron-donor tetrathiafulvalene moiety (exTTF). The resulting non-covalent hybrids have been characterized by different analytical, spectroscopic and microscopic techniques (TGA, Raman, UV-Vis absorption, TEM and XPS), and the supramolecular interaction of the molecular systems with graphene has been investigated by theoretical calculations. The electrochemical behavior of the pyrene-exTTF hybrids onto distinct graphene-based materi…

Bowl-shape electron donors with absorptions in the visible range of the solar spectrum and their supramolecular assemblies with C 60

We describe the synthesis, electronic, optical and photophysical properties of a family of three electron-donor bowl-shaped organic molecules that absorb light in the whole range of the visible spectrum (up to 800 nm in one case), and associate C60 in solution with binding constants in the range of 104–102 M−1 as measured from both UV-vis and fluorescence titrations in several solvents. These molecules are π-extended derivatives of tetrathiafulvalene, based on a truxene core to which two or three units of dithiole are covalently attached. The inclusion of the bulky dithiole groups is responsible for their bowl-shape geometry, which allows them to associate with C60, and their electron-donor…

Conformational Isomerism: Influence of the Z / E Isomerism on the Pathway Complexity of a Squaramide‐Based Macrocycle (Small 7/2021)

Cover Picture: Electron Transfer in a Supramolecular Associate of a Fullerene Fragment (Angew. Chem. Int. Ed. 8/2014)

Synthesis and optoelectronic properties of chemically modified bi-fluorenylidenes

The development of new light harvesting materials is a key issue for the progress of the research on organic & hybrid photovoltaics. Here, we report a new class of organic sensitizers based on the bi-fluorenylidene moiety as π-linker within the donor–π-linker–acceptor (D–π–A) scheme. The new dyes are endowed with electron donor and electron acceptor units at strategic positions in order to improve their electronic and light-harvesting properties. The comprehensive study of these compounds through the use of different experimental and theoretical techniques, provides an in-depth understanding of their electronic and photophysical properties, and reveal their interest as photovoltaic material…

Selenophene-Based Hole-Transporting Materials for Perovskite Solar Cells

Two novel and simple donor-π-bridge-donor (D-π-D) hole-transporting materials (HTMs) containing two units of the p-methoxytriphenylamine (TPA) electron donor group covalently bridged by means of the 3,4-dimethoxyselenophene spacer through single and triple bonds are reported. The optoelectronic and thermal properties of the new selenium-containing HTMs have been determined using standard experimental techniques and theoretical density functional theory (DFT) calculations. The selenium-based HTMs have been incorporated in mesoporous perovskite solar cells (PSCs) in combination with the triple-cation perovskite [(FAPbI3 )0.87 (MAPbBr3 )0.13 ]0.92 [CsPbI3 ]0.08 . Limited values of power conver…

Impact of the synergistic collaboration of oligothiophene bridges and ruthenium complexes on the optical properties of dumbbell-shaped compounds.

The linear and non-linear optical properties of a family of dumbbell-shaped dinuclear complexes, in which an oligothiophene chain with various numbers of rings (1, 3, and 6) acts as a bridge between two homoleptic tris(2,2'-bipyridine)ruthenium(II) complexes, have been fully investigated by using a range of spectroscopic techniques (absorption and luminescence, transient absorption, Raman, and non-linear absorption), together with density functional theory calculations. Our results shed light on the impact of the synergistic collaboration between the electronic structures of the two chemical moieties on the optical properties of these materials. Experiments on the linear optical properties …

In Silico Molecular Engineering of Dysprosocenium-Based Complexes to Decouple Spin Energy Levels from Molecular Vibrations

Molecular nanomagnets hold great promise for spintronics and quantum technologies, provided that their spin memory can be preserved above liquid-nitrogen temperatures. In the past few years, the magnetic hysteresis records observed for two related dysprosocenium-type complexes have highlighted the potential of molecular engineering to decouple vibrational excitations from spin states and thereby enhance magnetic memory. Herein, we study the spin-vibrational coupling in [(CpiPr5)Dy(Cp*)]+ (CpiPr5 = pentaisopropylcyclopentadienyl, Cp* = pentamethylcyclopentadienyl), which currently holds the hysteresis record (80 K), by means of a computationally affordable methodology that combines first-pri…

FT Raman and DFT Study on a Series of All-antiOligothienoacenes End-Capped with Triisopropylsilyl Groups

minal a positions. These substituents aid in purification and solution processability, and can be removed under mild chemical conditions. For the first time, we have the opportunity to analyze a series of oligothienoacenes to gain insight into the fundamental structure–property relationships with respect to the addition of each ring. Furthermore, this series of compounds can be directly compared to other well-studied series of closely related oligomers, such as nonfused oligothiophenes and fully fused all-syn oligothienoacenes. [7] To gain precise insight into relationships between the structure and properties of a wide range of p-conjugated molecular Herein, we study the p-conjugational pr…

DLPNO-CCSD(T) scaled methods for the accurate treatment of large supramolecular complexes

In this work, we present scaled variants of the DLPNO-CCSD(T) method, dubbed as (LS)DLPNO-CCSD(T) and (NS)DLPNO-CCSD(T), to obtain accurate interaction energies in supramolecular complexes governed by noncovalent interactions. The novel scaled schemes are based on the linear combination of the DLPNO-CCSD(T) correlation energies calculated with the standard (LoosePNO and NormalPNO) and modified (Loose2PNO and Normal2PNO) DLPNO-CCSD(T) accuracy levels. The scaled DLPNO-CCSD(T) variants provide nearly TightPNO accuracy, which is essential for the quantification of weak noncovalent interactions, with a noticeable saving in computational cost. Importantly, the accuracy of the proposed schemes is…

Ab Initio Modeling of Donor–Acceptor Interactions and Charge-Transfer Excitations in Molecular Complexes: The Case of Terthiophene–Tetracyanoquinodimethane

This work presents a thorough quantum chemical study of the terthiophene-tetracyanoquinodimethane complex as a model for π-π donor-acceptor systems. Dispersion-corrected hybrid (B3LYP-D) and double hybrid (B2PLYP-D), hybrid meta (M06-2X and M06-HF), and recently proposed long-range corrected (LC-wPBE, CAM-B3LYP, and wB97X-D) functionals have been chosen to deal with π-π intermolecular interactions and charge-transfer excitations in a balanced way. These properties are exhaustively compared to those computed with high-level ab initio SCS-MP2 and CASPT2 methods. The wB97X-D functional exhibits the best performance. It provides reliable intermolecular distances and interaction energies and pre…

Ternary Organic Solar Cell with a Near‐Infrared Absorbing Selenophene–Diketopyrrolopyrrole‐Based Nonfullerene Acceptor and an Efficiency above 10%

On the Structure and Chiral Aggregation of Liquid Crystalline Star‐Shaped Triazines H‐Bonded to Benzoic Acids

The ability of a star-shaped tris(triazolyl)triazine derivative to hierarchically build supramolecular chiral columnar organizations through the formation of H-bonded complexes with benzoic acids was studied from a theoretical and experimental point of view. The combined study has been done at three different levels including the study of the structure of the triazine core, the association with benzoic acids in stoichiometry 1:3, and the assembly of 1:3 complexes in helical aggregates. Although the star-shaped triazine core crystallizes in a non-C3 conformation, the C3 -symmetric conformation is theoretically predicted to be more stable and gives rise to a favorable C3 supramolecular 1:3 co…

A Columnar Liquid Crystal with Permanent Polar Order

et al.

A bis(triazole)benzamide receptor for the complexation of halide anions and neutral carboxylic acid guests. Guest-controlled topicity and self-assembly

Bis(triazole)benzamide 1 has been readily synthesized by means of Cu-catalyzed 1,3-dipolar cycloaddition and its ability to bind halide anions and neutral gallic acid derivative 12GA has been theoretically and experimentally investigated. The cavity defined by the N-H amide group and the vicinal aromatic hydrogens is suitable to form H-bonding arrays with halide guests. The stability of complexes 1·Cl- and 1·Br- is very similar, as DFT calculations predict and 1H NMR titration experiments confirm. The zigzag "anti" conformation of the molecule generates two regions with complementary positive and negative potentials that favor the statistical complexation of two molecules of the neutral car…

Hierarchy of Asymmetry at Work: Chain-Dependent Helix-to-Helix Interactions in Supramolecular Polymers.

A detailed investigation of the hierarchy of asymmetry operating in the self-assembly of achiral (1) and chiral ((S)-2 and (R)-3) 1,3,5-triphenylbenzenetricarboxamides (TPBAs) is reported. The aggregation of these TPBAs is conditioned by the point chirality at the peripheral side chains for (S)-2 and (R)-3. An efficient helix-to-helix interaction that goes further in the organization of fibrillar bundles is experimentally detected and theoretically supported only for the achiral TPBA 1. The effective interdigitation of the achiral aliphatic side chains produces a social self-sorting to form preferentially heterochiral macromolecular aggregates.

Charge-Separation and Charge-Recombination Rate Constants in a Donor–Acceptor Buckybowl-Based Supramolecular Complex: Multistate and Solvent Effects

The kinetics of the nonradiative photoinduced processes (charge-separation and charge-recombination) experimented in solution by a supramolecular complex formed by an electron-donating bowl-shaped truxene-tetrathiafulvalene (truxTTF) derivative and an electron-accepting fullerene fragment (hemifullerene, C30H12) has been theoretically investigated. The truxTTF·C30H12 heterodimer shows a complex decay mechanism after photoexcitation with the participation of several low-lying excited states of different nature (local and charge-transfer excitations) all close in energy. In this scenario, the absolute rate constants for all of the plausible charge-separation (CS) and charge-recombination (CR)…

Tuning the Self-Assembly of Rectangular Amphiphilic Cruciforms

The self-assembly of a series of nonionic amphiphilic cruciforms based on the 1,2,4,5-tetrakis(phenylethynyl)benzene (TPEB) skeleton, in which the peripheral substituents have been modified to modulate the morphology of the supramolecular structures, is reported. The presence of linear paraffinic and hydrophilic chains in TPEBs 1 and 2 gives rise to two-dimensional structures of high aspect ratio. In contrast, the incorporation of dendronized hydrophilic chains results in the formation of twisted ribbons in amphiphile 3 and impedes the organized self-assembly of TPEB 4. Theoretical calculations show that the self-assembly of these amphiphiles might be initiated with the formation of π-stack…

Non-Planar and Flexible Hole-Transporting Materials from Bis-Xanthene and Bis-Thioxanthene Units for Perovskite Solar Cells

Two new hole-transporting materials (HTMs), BX-OMeTAD and BTX-OMeTAD, based on xanthene and thioxanthene units, respectively, and bearing p-methoxydiphenylamine peripheral groups, are presented for their use in perovskite solar cells (PSCs). The novelty of the newly designed molecules relies on the use of a single carbon-carbon bond ‘C−C’ as a linker between the two functionalized heterocycles, which increases the flexibility of the molecule compared with the more rigid structure of the widely used HTM spiro-OMeTAD. The new HTMs display a limited absorbance in the visible region, due to the lack of conjugation between the two molecular halves, and the chemical design used has a remarkably i…

Diferrocenyl oligothiophene wires: Raman and quantum chemical study of valence-trapped cations

A combination of Raman spectroscopy and density functional theory calculations is used to describe the structural and spectroscopic properties of the different isomeric cations of diferrocenyl quaterthiophenes. Isomerisation of the thienyl β-positions provides site selective oxidation, which gives rise to species that can interconvert by moving the charge over the bridge. The spectroscopic study allows us to describe a sequence of stationary trapped cationic, either ferrocenyl or thienyl, states which constitutes an energy cascade of accessible sites through which the charge transfer can proceed.

Heteroatom Effect on Star-Shaped Hole-Transporting Materials for Perovskite Solar Cells

High Yield Ultrafast Intramolecular Singlet Exciton Fission in a Quinoidal Bithiophene

We report the process of singlet exciton fission with high-yield upon photoexcitation of a quinoidal thiophene molecule. Efficient ultrafast triplet photogeneration and its yield are determined by photoinduced triplet-triplet absorption, flash photolysis triplet lifetime measurements, as well as by femtosecond time-resolved transient absorption and fluorescence methods. These experiments show that optically excited quinoidal bithiophene molecule undergoes ultrafast formation of the triplet-like state with the lifetime ∼57 μs. CASPT2 and RAS-SF calculations have been performed to support the experimental findings. To date, high singlet fission rates have been reported for crystalline and pol…

Non-covalent graphene nanobuds from mono- and tripodal binding motifs.

Graphene nanobuds were prepared via the non-covalent anchoring of C60-based molecules endowed with one or three pyrene units, respectively. TGA, FTIR, UV-Vis and TEM investigations confirmed the formation of nanohybrids. For the two molecular derivatives, striking differences were determined in their interaction with graphene or carbon surfaces by Raman, cyclic voltammetry and molecular mechanics calculations, revealing the important role of pyrene adsorption in modulating the electronic properties of the nanohybrids.

Self-assembly of Clicked Star-Shaped Triazines into Functional Nanostructures

Two non‐amphiphilic star‐shaped 2,4,6‐tris(1,2,3‐triazol‐4‐yl)‐1,3,5‐triazines showing different behavior in terms of self‐assembly and luminescent properties are described. They aggregate in the liquid phase to form low‐dimensional nanostructures with a variety of morphologies, such as spherical particles, one‐hole hollow spheres, toroids, twisted fibers or helical nanotubes, just by varying the conditions of a straightforward reprecipitation method. Aggregation has an opposite effect concerning the fluorescent properties of the proposed compounds, either causing the enhancement or the quenching of the emission after the self‐assembly. Quantum chemical calculations have been also performed…

Influence of theZ/EIsomerism on the Pathway Complexity of a Squaramide‐Based Macrocycle

The rising interest on pathway complexity in supramolecular polymerization has prompted the finding of novel monomer designs able to stabilize kinetically trapped species and generate supramolecular polymorphs. In the present work, the exploitation of the Z/E (geometrical) isomerism of squaramide (SQ) units to produce various self-assembled isoforms and complex supramolecular polymerization pathways in methylcyclohexane/CHCl3 mixtures is reported for the first time. This is achieved by using a new bissquaramidic macrocycle (MSq) that self-assembles into two markedly different thermodynamic aggregates, AggA (discrete cyclic structures) and AggB (fibrillar structures), depending on the solven…

Hole transporting materials based on benzodithiophene and dithienopyrrole cores for efficient perovskite solar cells

The development of highly efficient hole transporting materials (HTMs) for perovskite solar cells (PSCs) is still one of the most thrilling research subjects in the development of this emerging photovoltaic technology. Inner ring engineering of the aromatic core of new HTMs – consisting of three fused rings endowed with four triarylamine units – reveals major performance effects over the fabricated devices. In particular, substitution of the central pyrrole ring in dithienopyrrole (DTP) by a benzene ring – benzodithiophene (BDT) – allows enhancing the power conversion efficiency from 15.6% to 18.1%, in devices employing mixed-perovskite (FAPbI3)0.85(MAPbBr3)0.15 (MA: CH3NH3+, FA: NHCHNH3+) …

Effect of molecular geometry and extended conjugation on the performance of hydrogen-bonded semiconductors in organic thin-film field-effect transistors

A general synthetic method has been used for the condensation of the 7-azaindole substructure at both extremes of centrosymmetric fused polyheteroaromatic systems. Four different aromatic spacers (benzene, naphthalene, anthracene and pyrene) that modify the molecular geometry and the π-conjugated surface have proved the ability of 7-azaindole to work as a building block that can control the crystal packing through reciprocal hydrogen bond interactions. Two possible self-assembled columnar arrangements have been observed as a result of the π–π interactions between hydrogen-bonded ribbon-like supramolecular structures. A detailed comparative analysis of the molecular organisation driven by hy…

The Nonlocal Correlation Density Functional VV10

Abstract In this chapter, we review the most relevant attempts to merge the Vydrov and van Voorhis nonlocal density-dependent functional kernel (VV10) with modern density functionals to accurately describe van der Waals interactions with a reasonable computational cost. The chapter is organized by providing first an introduction of the relevance of van der Waals interactions and the difficulties of common density functionals to describe these forces. Second, the historical developments that eventually give rise to the most modern formulation of the nonlocal density functional VV10 are briefly addressed. Then, an overview of its technical formulation, adjustable parameters, and implementatio…

Improving the Long‐Term Stability of Doped Spiro‐Type Hole‐Transporting Materials in Planar Perovskite Solar Cells

The improvement of the long-term stability of perovskite-based solar cells (PSCs) toward commercialization is closely linked to the development of cutting-edge charge-transporting materials. The progress on the design and the synthesis of new hole-transporting materials (HTMs) is synergistically attaining both top efficiencies and promising stability. Herein, the synthesis and characterization of two doped-HTMs based on electron-rich spiranic cores, namely, 9H-quinolinophenoxazine (spiro-POZ) and 9H-quinolinophenothiazine (spiro-PTZ), are presented. The novel HTMs exhibit excellent solubility, optimal highest occupied molecular orbital energy, and excellent thermal stability with glass tran…

Self-Assembly-Directed Organization of a Fullerene–Bisporphyrin into Supramolecular Giant Donut Structures for Excited-State Charge Stabilization

Functional materials composed of spontaneously self-assembled electron donor and acceptor entities capable of generating long-lived charge-separated states upon photoillumination are in great demand as they are key in building the next generation of light energy harvesting devices. However, creating such well-defined architectures is challenging due to the intricate molecular design, multistep synthesis, and issues associated in demonstrating long-lived electron transfer. In this study, we have accomplished these tasks and report the synthesis of a new fullerene–bis-Zn-porphyrin e-bisadduct by tether-directed functionalization of C60 via a multistep synthetic protocol. Supramolecular oligom…

Exploiting multivalent nanoparticles for the supramolecular functionalization of graphene with a nonplanar recognition motif.

The supramolecular modification of planar graphene with the geometri- cally mismatched, curved 9,10-di(1,3-dithiole-2-ylidene)-9,10-dihydroanthracene (exTTF) molecule is demonstrated. The exTTF-graphene interaction is governed by p-p and CH-p interactions, with a negligible contribution from charge transfer. We amplified these weak forces through multivalent gold nanoparticles. Our re- sults show that planarity is not a prerequisite for recognition motifs for graphene.

Decoding the Consequences of Increasing the Size of Self-Assembling Tricarboxamides on Chiral Amplification

A complete series of experimental and theoretical investigations on the supramolecular polymerization of chiral (1 and 2) and achiral (3) oligo(phenylene ethynylene) tricarboxamides (OPE-TAs) is reported. The performance of seargents-and-soldiers (SaS) and majority rules (MR) experiments has allowed deriving a full set of thermodynamic parameters, including the helix reversal penalty (HRP) and the mismatch penalty (MMP). The results described illustrate the influence exerted by the number of stereogenic centers per monomeric unit and the temperature on the chiral amplification phenomenon. While the HRP decreases upon decreasing the number of chiral side chains, the MMP follows an opposite t…

Non-Centrosymmetric Homochiral Supramolecular Polymers of Tetrahedral Subphthalocyanine Molecules

This is the peer reviewed version of the following article: Angewandte Chemie - International Edition 54.8 (2015): 2543-2547, which has been published in final form at http://dx.doi.org/10.1002/anie.201411272. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving

Hole-Transporting Materials for Perovskite Solar Cells Employing an Anthradithiophene Core

A decade after the report of the first efficient perovskite-based solar cell, development of novel hole-transporting materials (HTMs) is still one of the main topics in this research field. Two of the main advance vectors of this topic lie in obtaining materials with enhanced hole-extracting capability and in easing their synthetic cost. The use of anthra[1,9-bc:5,10-b'c']dithiophene (ADT) as a flat π-conjugated frame for bearing arylamine electroactive moieties allows obtaining two novel highly efficient HTMs from very cheap precursors. The solar cells fabricated making use of the mixed composition (FAPbI3)0.85(MAPbBr3)0.15 perovskite and the novel ADT-based HTMs show power conversion effi…

Conjugated Porphyrin Dimers: Cooperative Effects and Electronic Communication in Supramolecular Ensembles with C60

International audience; Two new conjugated porphyrin-based systems (dimers 3 and 4) endowed with suitable crown ethers have been synthesized as receptors for a fullerene-ammonium salt derivative (1). Association constants in solution have been determined by UV–vis titration experiments in CH2Cl2 at room temperature. The designed hosts are able to associate up to two fullerene-based guest molecules and present association constants as high as ∼5 × 108 M–1. Calculation of the allosteric cooperative factor α for supramolecular complexes [3·12] and [4·12] showed a negative cooperative effect in both cases. The interactions accounting for the formation of the associates are based, first, on the …

Tetrathiafulvalene-Based Mixed-Valence Acceptor-Donor-Acceptor Triads: A Joint Theoretical and Experimental Approach

This work presents a joint theoretical and experimental characterisation of the structural and electronic properties of two tetrathiafulvalene (TTF)-based acceptor-donor-acceptor triads (BQ-TTF-BQ and BTCNQ-TTF - BTCNQ; BQ is naphthoquinone and BTCNQ is benzotetracyano-p-quinodimethane) in their neutral and reduced states. The study is performed with the use of electrochemical, electron paramagnetic resonance (EPR), and UV/Vis/NIR spectroelectrochemical techniques guided by quantum-chemical calculations. Emphasis is placed on the mixed-valence properties of both triads in their radical anion states. The electrochemical and EPR results reveal that both BQ-TTF-BQ and BTCNQ-TTF-BTCNQ triads in…

Oligothienoacenes versus oligothiophenes: Impact of ring fusion on the optical properties

The impact of backbone rigidity on the optical properties of thiophene-based compounds is studied by analyzing in detail the geometrical, electronic, optical and vibronic features of a family of oligothienoacenes (nnTAs) in comparison to non-fused α-oligothiophenes (nnTs) by means of quantum-chemical calculations. Ring fusion in nnTAs provokes a greater conjugation in the ground state. However, the change in the bond length alternation upon electronic excitation is very similar in both systems, which is also reflected in a similar evolution of the first optical transition energy with increasing oligomer size. Larger transition energies in nnTAsvs.nnTs arise from an electronic effect rather …

Nonlocal van der Waals Approach Merged with Double-Hybrid Density Functionals: Toward the Accurate Treatment of Noncovalent Interactions

Noncovalent interactions drive the self-assembly of weakly interacting molecular systems to form supramolecular aggregates, which play a major role in nanotechnology and biochemistry. In this work, we present a thorough assessment of the performance of different double-hybrid density functionals (PBE0-DH-NL, revPBE0-DH-NL, B2PLYP-NL, and TPSS0-DH-NL), as well as their parent hybrid and (meta)GGA functionals, in combination with the most modern version of the nonlocal (NL) van der Waals correction. It is shown that this nonlocal correction can be successfully coupled with double-hybrid density functionals thanks to the short-range attenuation parameter b, which has been optimized against ref…

Carbonyl-functionalized quaterthiophenes: a study of the vibrational Raman and electronic absorption/emission properties guided by theoretical calculations.

This work investigates the evolution of the molecular, vibrational, and optical properties within a family of carbonyl-functionalized quaterthiophenes: 5,5'''-diheptanoyl-2,2':5',2'':5'',2'''-quaterthiophene (1), 5,5'''-diperfluorohexylcarbonyl-2,2':5',2'':5'',2'''-quaterthiophene (2), and 2,7-[bis(5-perfluorohexylcarbonylthien-2-yl)]-4H-cyclopenta[2,1-b:3,4-b']-dithiophene-4-one (3). The analysis is performed by Raman and UV/Vis absorption/excitation/fluorescence spectroscopy in combination with density functional calculations. Theoretical calculations show that substitution with carbonyl groups and perfluorohexyl chains induces progressive quinoidization of the π-conjugated backbone in co…

Perovskite Solar Cells: Heteroatom Effect on Star-Shaped Hole-Transporting Materials for Perovskite Solar Cells (Adv. Funct. Mater. 31/2018)

Thermodynamic study of the interaction of long open-chain polyazaalkanes with cobalt(II) and nickel(II) ions

Complexation equilibria between the open-chain terminally methylated polyamines 1,14-bis(methylamino)-3,6,9,12- tetraazatetradecane (L1), 1,17-bis(methylamino)-3,6,9,12,15-pentaazaheptadecane (L2), 1,20-bis(methylamino)- 3,6,9,12,15,18-hexaazaicosane (L3) and 1,23-bis(methylamino)-3,6,9,12,15,18,21-heptaazatricosane (L4) with Co2+ and Ni2+ have been studied by means of potentiometric and spectrophotometric methods in 0.15 mol dm−3 NaClO4 aqueous solution at 298.15 K The stability constants for the complexes formed have been determined from e.m.f, data. All these ligands form mononuclear ML2+ complexes of similar stability with Co2+ and Ni2+. Binuclear Co2L44+, Ni2L34+ and Ni2L44+ are also f…

Binding Sites, Vibrations and Spin-Lattice Relaxation Times in Europium(II)-Based Metallofullerene Spin Qubits.

Abstract To design molecular spin qubits with enhanced quantum coherence, a control of the coupling between the local vibrations and the spin states is crucial, which could be realized in principle by engineering molecular structures via coordination chemistry. To this end, understanding the underlying structural factors that govern the spin relaxation is a central topic. Here, we report the investigation of the spin dynamics in a series of chemically designed europium(II)‐based endohedral metallofullerenes (EMFs). By introducing a unique structural difference, i. e. metal‐cage binding site, while keeping other molecular parameters constant between different complexes, these manifest the ke…

Impact of Molecular Size and Shape on the Supramolecular Co‐Assembly of Chiral Tricarboxamides: A Comparative Study

We report herein a comparative investigation of the chiral amplification features of a series of three families of C 3 -symmetric tricarboxamides: 1,3,5-triphenylbenzenetricarboxamides (TPBAs), benzenetricarboxamides (BTAs) and oligo(phenylene ethynylene) tricarboxamides (OPE-TAs). As previously observed for BTAs and OPE-TAs, a similar dichroic response is obtained for TPBAs decorated with three, two or only one chiral side chain bearing stereogenic centers, thus confirming the efficient transfer of point chirality to the supramolecular helical aggregates. Unlike BTAs and OPE-TAs, the chiral amplification ability of TPBAs in majority rules experiments shows a negligible dependence on the nu…

Saddle-like, π-conjugated, cyclooctatetrathiophene-based, hole-transporting material for perovskite solar cells

A flexible, saddle-like, π-conjugated skeleton composed of four fused thiophene rings forming a cyclooctatetrathiophene (CoTh) with four triphenylamines (CoTh-TTPA) is presented as a hole-transporting material (HTM) for perovskite solar cells. The new HTM shows a bright red color stemming from a direct conjugation between the TPA groups and the central CoTh scaffold. This results in a charge transfer band due to the combination of the weak acceptor moiety, the CoTh unit, and the electron-donating p-methoxytriphenylamine groups. CoTh-TTPA exhibits a suitable highest-occupied molecular orbital (HOMO) level in relation to the valence band edge of the perovskite, which ensures efficient hole ex…

High‐Efficiency Perovskite Solar Cells Using Molecularly Engineered, Thiophene‐Rich, Hole‐Transporting Materials: Influence of Alkyl Chain Length on Power Conversion Efficiency

The synthesis and characterization of a series of novel small-molecule hole-transporting materials (HTMs) based on an anthra[1,2-b:4,3-b′:5,6-b′′:8,7-b′′′]tetrathiophene (ATT) core are reported. The new compounds follow an easy synthetic route and have no need of expensive purification steps. The novel HTMs are tested in perovskite solar cells and power conversion efficiencies (PCE) of up to 18.1% under 1 sun irradiation are measured. This value is comparable with the 17.8% efficiency obtained using 2,2′,7,7′-tetrakis(N,N-di-p-methoxyphenylamine)-9,9′-spirobifluorene as a reference compound. Similarly, a significant quenching of the photoluminescence in the first nanosecond is observed, ind…

Photophysical Properties of Oligo(phenylene ethynylene) Iridium(III) Complexes Functionalized with Metal-Anchoring Groups

[EN] The electrochemical and photophysical properties of a family of conjugated ligands and their iridium(III) cyclometallated complexes are described. They consist of a series of monocationic Ir-III bis-2-phenylpyridine complexes with p-phenylethynyl-1,10-phenanthroline ligands of different length. The structure of these ligands includes terminal acetylthiol or pyridine groups, which can provide good electrical contacts between metal electrodes. Cyclic voltammetry, absorption and emission spectroscopy, laser flash photolysis and density functional theory calculations reveal that the high conjugation of the diimine ligand affords small energy gaps between the frontier orbitals. Nevertheless…

Electron transfer in a supramolecular associate of a fullerene fragment

Herein, we investigate the association of a fullerene fragment, hemifullerene C30H12, with an electron-donating bowl-shaped tetrathiafulvalene derivative (truxTTF). UV/Vis titrations and DFT calculations support formation of the supramolecular complex, for which an association constant of log Ka = 3.6±0.3 in CHCl3 at room temperature is calculated. Remarkably, electron transfer from truxTTF to C30H12 to form the fully charge-separated species takes place upon irradiation of the associate with light, constituting the first example in which a fullerene fragment mimics the electron-accepting behavior of fullerenes within a supramolecular complex.

Cover Feature: Self-Assembly of Clicked Star-Shaped Triazines into Functional Nanostructures (ChemNanoMat 1/2019)

Azatruxene‐Based, Dumbbell‐Shaped, Donor–π‐Bridge–Donor Hole‐Transporting Materials for Perovskite Solar Cells

Three novel donor-π-bridge-donor (D-π-D) hole-transporting materials (HTMs) featuring triazatruxene electron-donating units bridged by different 3,4-ethylenedioxythiophene (EDOT) π-conjugated linkers have been synthesized, characterized, and implemented in mesoporous perovskite solar cells (PSCs). The optoelectronic properties of the new dumbbell-shaped derivatives (DTTXs) are highly influenced by the chemical structure of the EDOT-based linker. Red-shifted absorption and emission and a stronger donor ability were observed in passing from DTTX-1 to DTTX-2 due to the extended π-conjugation. DTTX-3 featured an intramolecular charge transfer between the external triazatruxene units and the azo…

Distance Matters: Biasing Mechanism, Transfer of Asymmetry, and Stereomutation in N-Annulated Perylene Bisimide Supramolecular Polymers

International audience; The synthesis of two series of N-annulated perylene bisimides (PBIs), compounds 1 and 2, is reported, and their self-assembling features are thoroughly investigated by a complete set of spectroscopic measurements and theoretical calculations. The study corroborates the enormous influence that the distance between the PBI core and the peripheral groups exerts on the chiroptical properties and the supramolecular polymerization mechanism. Compounds 1, with the peripheral groups separated from the central PBI core by two methylenes and an ester group, form J-type supramolecular polymers in a cooperative manner but exhibit negligible chiroptical properties. The lack of cl…

Metal-atom impact on the self-assembly of cup-and-ball metalloporphyrin–fullerene conjugates

International audience; A fullerene ammonium derivative has been combined with different metalloporphyrin–crown ether receptors to generate very stable supramolecules. The combination of fullerene–porphyrin and ammonium–crown ether interactions leads to a strong chelate effect as evidenced by a high effective molarity (3.16 M). The different parameters influencing the stability of the supramolecular ensembles, in particular the nature of the metal in the porphyrin moiety, have been rationalized with the help of theoretical calculations thus providing new insights into fullerene–porphyrin interactions.

Minimizing geminate recombination losses in small-molecule-based organic solar cells

Small-molecule-based organic solar cells (OSCs) are a recurrent alternative to polymer-based OSCs. Due to the higher purity and definition of small molecules compared to polymers, the morphological requirements can be more relaxed. Here, we present a series of novel rhodanine-based small-molecule electron donors and blend them with the standard acceptor PC70BM. By performing a target analysis on femtosecond spectroscopy data, we quantify the rates of geminate charge recombination. We are able to reproduce these rates by applying the Marcus–Levich–Jortner equation, using results from quantum chemical calculations. This shows that in a series of differently substituted compounds, one can corr…

Bending Carbon Nanoforms for Supramolecular Recognition: A Topological Study on Hemifullerene-Based Aggregates

International audience; Buckybowls have risen as appealing fullerene fragment derivatives. Their intrinsic curvature has been exploited in the generation of host–guest supramolecular assemblies, not only through concave–convex complementarity but also through less-known concave–concave staggered arrangements. Whereas the stabilization of bowl-in-bowl dispositions has been ascribed to efficient π–π forces together with favorable dipole–dipole interactions, a detailed analysis on the forces guiding the formation of the staggered arrangements is missing so far. Herein, we present a thorough theoretical characterization of bowl-in-bowl vs staggered hemifullerene-based homodimers and heterodimer…

Flipping Motion To Bias the Organized Supramolecular Polymerization of N-Heterotriangulenes

Synergistic experimental and theoretical studies have allowed the disentangling of the possible pathways for the supramolecular polymerization of a series of dicyanovinyl-bridged N-heterotriangulene (NHT) derivatives bearing benzamide units with achiral (1a) and chiral (1b,c) side chains. The synthesis of these bowl-shaped, self-assembling units yields a mixture of monomeric species with C3- and C1-symmetry. Both monomeric species are able to self-assemble into different supramolecular aggregates with sufficient stability to coexist in freshly prepared solutions. The dissimilar ratio of the aggregates initially generated results in different spectroscopic features and, more specifically, in…

Quantum-Chemical Insights into the Self-Assembly of Carbon-Based Supramolecular Complexes

Understanding how molecular systems self-assemble to form well-organized superstructures governed by noncovalent interactions is essential in the field of supramolecular chemistry. In the nanoscience context, the self-assembly of different carbon-based nanoforms (fullerenes, carbon nanotubes and graphene) with, in general, electron-donor molecular systems, has received increasing attention as a means of generating potential candidates for technological applications. In these carbon-based systems, a deep characterization of the supramolecular organization is crucial to establish an intimate relation between supramolecular structure and functionality. Detailed structural information on the se…

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