Nonfullerene Polymer Solar Cells Reaching a 9.29% Efficiency Using a BODIPY-Thiophene Backboned Donor Material

A conjugated polymer donor containing BODIPY-thiophene dyads in the backbone, P(BdP-EHT), combined with a low bandgap nonfullerene acceptor (SMDPP) consisting of carbazole and diketopyrrolopyrrole units linked with a tetracyanobutadiene acceptor π-linker, was used to design bulk heterojunction polymer solar cells. After the optimization of the donor to acceptor weight ratio and solvent vapor annealing of the P(BdP-EHT):SMDPP active layer, the resulting polymer solar cell showed an overall power conversion efficiency of 9.29%, which is significantly higher than that for the polymer solar cell based on PC71BM (7.41%) processed under identical conditions. This improved power conversion efficie…

Two-Photon Absorption Properties and Structures of BODIPY and Its Dyad, Triad and Tetrad.

A series consisting of a dyad, a triad and a tetrad containing either two, three and four BODIPY units, respectively, has been synthesized and fully characterized and compared to two mono-BODIPY analogs (used as references). The one- and two-photon photophysical properties have been measured and the X-ray structures of four of the BODIPY derivatives have been determined. In the 700-900 nm range, the two-photon absorption (TPA) cross sections range from 30 GM to 160 GM for these compounds.

Random Structural Modification of a Low-Band-Gap BODIPY-Based Polymer

International audience; A BODIPY thiophene polymer modified by extending conjugation of the BODIPY chromophore is reported. This modification induces tunability of energy levels and therefore absorption wavelengths in order to target lower energies.

Antipoxvirus Activity Evaluation of Optimized Corroles Based on Development of Autofluorescent ANCHOR Myxoma Virus

International audience; A series of 43 antiviral corrole-based molecules have been tested on myxoma virus (Lausanne-like T1MYXV strain). An autofluorescent MYXV, with an ANCHOR cassette, has been used for the studies. A(2)B-fluorocorroles display various toxicities, from 40 being very toxic (CC50 = 1.7 mu M) to nontoxic 38 (CC50 > 50 mu M), whereas A(3)-fluorocorroles, with one to three fluorine atoms, are not toxic (with the exception of corroles 9, 10, and 22). In vitro, these compounds show a good selectivity index when used alone. Corrole 35 seems to be the most promising compound, which displays a high selectivity index with the lowest IC50. Interestingly, this "Hit" corrole is easy to…

Synthesis, Electrochemistry, and Photophysics of Aza-BODIPY Porphyrin Dyes

International audience; The synthesis of dyad and triad aza-BODIPY-porphyrin systems in two steps starting from an aryl-substituted aza-BODIPY chromophore is described. The properties of the resulting aza-BODIPY-porphyrin conjugates have been extensively investigated by means of electrochemistry, spectroelectrochemistry, and absorption/emission spectroscopy. Fluorescence measurements have revealed a dramatic loss of luminescence intensity, mainly due to competitive energy transfer and photoinduced electron transfer involving charge separation followed by recombination.

A bacteriochlorin-diketopyrrolopyrrole triad as a donor for solution-processed bulk heterojunction organic solar cells

We have designed an A–π–D–π–A small-molecule triad consisting of a bacteriochlorin (BC) donor central core linked with two diketopyrrolopyrrole (DPP) acceptors via ethynyl bridges (BC-DPP-1). BC-DPP-1 has a narrow optical bandgap of 1.38 eV with highest occupied molecular orbital and lowest unoccupied molecular orbital energy levels of −4.93 eV and −3.40 eV, respectively, and it was used as an electron donor along with [6,6]-phenyl-C71-butyric acid methyl ester (PC71BM) as an acceptor for solution-processed small-molecule organic solar cells. After optimizing the weight ratio between BC-DPP-1 and PC71BM and pyridine as a solvent additive and subsequent solvent vapor annealing using THF, an …

Polymer solar cell based on ternary active layer consists of medium bandgap polymer and two non-fullerene acceptors

Abstract An efficient PSCs consisting of a ternary active layer containing a medium bandgap conjugated polymer P and two well-known non-fullerene acceptors i.e. ITIC-m and Y6 was fabricated. An overall Power Conversion Efficiency (PCE) of about 15.13% was achieved, with the optimized ternary active layer consisting of 20 wt% of ITIC-m in acceptors i.e. P:ITIC-m:Y6 (1:0.3:1.2). This value is higher than that for the binary counter parts i.e. 12.10% and 13.16% for P:ITIC-m (1:1.5 w:w) and P:Y6 (1:1.5 w:w). The higher short circuit current density of the ternary active layer PSCs is related to the broader absorption spectra as compared to the binary active layer analogs. The open circuit volta…

Inside Cover: Synthesis and Characterization of Carbazole-Linked Porphyrin Tweezers (Chem. Eur. J. 34/2015)

Porphyrins and BODIPY as Building Blocks for Efficient Donor Materials in Bulk Heterojunction Solar Cells

International audience; Advances in the synthesis and application of highly efficient polymers and small molecules over the last two decades have enabled the rapid advancement in the development of organic solar cells and photovoltaic technology as a promising alternative to conventional solar cells, based on silicon and other inorganic semiconducting materials. Among the different types of organic semiconducting materials, porphyrins and BODIPY-based small molecules and conjugated polymers attract high interest as efficient semiconducting organic materials for dye sensitized solar cells and bulk heterojunction organic solar cells. The highest power conversion efficiency exceeding 9% has be…

Photovoltaic Properties of a Porphyrin-Containing Polymer as Donor in Bulk Heterojunction Solar Cells With Low Energy Loss

BODIPY–diketopyrrolopyrrole–porphyrin conjugate small molecules for use in bulk heterojunction solar cells

Two small molecules denoted as BD-pPor and BD-tPor composed of a central BODIPY core surrounded with two DPP and two porphyrin units have been designed and synthesized. In BD-pPor and BD-tPor, porphyrins are linked to the central BODIPY by phenyl and thiophene bridges, respectively. The optical and electrochemical properties were systematically investigated in order to employ them as donors along with PC71BM as an acceptor for solution processed bulk heterojunction organic solar cells. After the optimization of the active layer, the organic solar cells based on BD-pPor and BD-tPor exhibit overall power conversion efficiencies of 6.67% and 8.98% with an energy loss of 0.63 eV and 0.50 eV. Th…

Cyclotriveratrylene-Containing Porphyrins

International audience; The C-3-symmetric cyclotriveratrylene (CTV) was covalently bonded via click chemistry to 1, 2, 3, and 6 zinc(II) porphyrin units to various host for C-60. The binding constants, Ka, were measured from the quenching of the porphyrin fluorescence by C-60. These constants vary between 400 and 4000 M-1 and are considered weak. Computer modeling demonstrated that the zinc(II) porphyrin units, [Zn], exhibit a strong tendency to occupy the CTV cavity, hence blocking the access for C-60 to land on this site. Instead, the pincer of the type [Zn]-[Zn] and in one case [Zn]-CTV, were found to be the most probable geometry to promote host-guest associations in these systems.

Synthesis and characterization of zinc carboxy–porphyrin complexes for dye sensitized solar cells

Two zinc porphyrins, 2 and 8, have been synthesized. Porphyrin 8 displays better electronic communication between the dye and the TiO2 electrode. Photophysical measurements and electrochemistry experiments suggest that both porphyrins are very promising sensitizers for dye-sensitized solar cells (DSSCs). It was found that their molecular orbital energy levels favor electron injection and dye regeneration in DSSCs. Solar cells sensitized by 2 and 8 were fabricated, and it was found that they show power conversion efficiencies (PCEs) of 5.27% and 7.13%, respectively. Photovoltaic measurements (J–V curves) together with the incident photon-to-electron conversion efficiency spectra of the two c…

Porphyrin Antenna-Enriched BODIPY–Thiophene Copolymer for Efficient Solar Cells

International audience; Low bandgap A−π–D copolymer, P(BdP-DEHT), consisting of alternating BOronDIPYrromethene (BODIPY) and thiophene units bridged by ethynyl linkers, and its porphyrin-enriched analogue, P(BdP/Por-DEHT), were prepared, and their optical and electrochemical properties were studied. P(BdP-DEHT) exhibits strong absorption in the 500–800 nm range with an optical bandgap of 1.74 eV. On the basis of cyclic voltammetry, the highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energy levels are evaluated to be −5.40 and −3.66 eV, respectively. After the anchoring of zinc(II) porphyrin on the BODIPY unit, P(BdP/Por-DEHT) displays broadened absor…

Synthesis and Characterization of Carbazole-Linked Porphyrin Tweezers

Herein the synthesis, spectroscopic characterization, two-photon absorption and electrochemical properties of 3,6-disubstituted carbazole tweezers is reported. A dimer resulting from a Glaser homocoupling was isolated during a Sonogashira coupling reaction between a diethynyl-carbazole spacer and a 5-bromo-triarylporphyrin and the properties of this original compound were compared with the 3,6-disubstituted carbazole bisporphyrin tweezers. The dyads reported herein present a two-photon absorption maximum at 920 nm with two-photon absorption cross-section in the 1200 GM range. Despite a strong linear absorption in the Soret region and moderate fluorescence quantum yield, they both lead to a …

A3- and A2B-fluorocorroles: synthesis, X-ray characterization and antiviral activity evaluation against human cytomegalovirus infection

Twenty-nine fluorinated corroles were prepared, spectroscopically characterized, and studied for their antiviral activity against human cytomegalovirus infection. Six corroles were also fully characterized by X-ray crystallography giving insights on their geometrical features. The halogenated corroles reported herein exhibit significantly improved antiviral activity over their non-halogenated counterparts and over nitro-corrole analogs previously reported. Full activity of thirteen A3-corroles is achieved with four fluorine atoms present on the meso-phenyl ring reaching a selectivity index above 300. The maximum activity is achieved for A2B-corroles with selectivity indexes above 400. We th…

A Very Low Band Gap Diketopyrrolopyrrole-Porphyrin Conjugated Polymer

International audience; A porphyrin-diketopyrrolopyrrole-containing polymer (poly(porphyrin-diketopyrrolopyrrole) (PPDPP)) shows impressive molar absorption coefficients from lambda=300 to 1000 nm. The photophysical and structural properties of PPDPP have been studied. With PPDPP as the electron donor and [ 6,6]phenyl C-71 butyric acid methyl ester (PC71BM) as the electron acceptor, the bulk heterojunction polymer solar cell showed overall power conversion efficiencies of 4.18 and 6.44% for as-cast and two-step annealing processed PPDPP: PC71BM (1: 2) active layers, respectively. These results are quite impressive for porphyrin-containing polymers, especially when directly included in the p…

Near-infrared emissive bacteriochlorin-diketopyrrolopyrrole triads: Synthesis and photophysical properties

International audience; The synthesis of unprecedented energy transfer triads containing a near-infrared (NIR) emissive bacteriochlorin subunit and two diketopyrrolopyrrole (DPP) moieties linked to each other via ethynyl or zero-carbon spacers is presented. Their optical and fluorescence properties were determined in CHCl3 and toluene. These photophysical measurements highlight the ability of DPP scaffold to act as an effective energy donor, which once excited in the range 450-550 nm resulting nearly exclusively NIR emission of hydroporphyrin (ETE > 96%). Since DPP dyes are valuable structurally tunable fluorophores that may be used in the construction of high-performance multicomponent pho…

A3- and A2B-nitrocorroles: synthesis and antiviral activity evaluation against human cytomegalovirus infection

Human cytomegalovirus (hCMV) is responsible for several pathologies impacting immunocompromised patients and can trigger life-threatening infection. Several antivirals are available and are used in the clinic, but hCMV resistant strains have appeared and patients have encountered therapeutic failure. Hence, there is a constant need for new best in class or first in class antiviral molecules. We have previously shown that nitrocorroles could be used as a potent anti-hCMV agent without acute toxicity in mice. They therefore represent an excellent platform to perform structure–activity relationship (SAR) studies and to increase efficiency or reduce toxicity. We have generated original A2B- and…

CCDC 1910519: Experimental Crystal Structure Determination

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CCDC 1830060: Experimental Crystal Structure Determination

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CCDC 1830057: Experimental Crystal Structure Determination

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CCDC 1910517: Experimental Crystal Structure Determination

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CCDC 1910516: Experimental Crystal Structure Determination

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CCDC 1830059: Experimental Crystal Structure Determination

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CCDC 1910518: Experimental Crystal Structure Determination

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CCDC 1910052: Experimental Crystal Structure Determination

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CCDC 1910515: Experimental Crystal Structure Determination

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CCDC 1910514: Experimental Crystal Structure Determination

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CCDC 1830058: Experimental Crystal Structure Determination

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