0000000001300194
AUTHOR
Marco Saccone
On the blue phase structure of hydrogen-bonded liquid crystals via 19F NMR
Abstract 19 F NMR spectra are simulated for blue phase I of FPHG( St 1.5 ∗ Ap 1.5 ) based on a model of a double-twisted substructure inside cylinders that form a body-centred cubic lattice. A kinetic matrix is included to describe jump processes over quarter pitch lengths. Though the lines in the NMR spectra are broad and featureless, changes in the widths and positions with temperature are well described by the blue phase model structure. The spectra in the chiral nematic N∗ phase are also simulated. Dynamics in the BP I are found to be slower than in the N∗ phase.
Efficient light-induced phase transitions in halogen-bonded liquid crystals
Here, we present a new family of light-responsive, fluorinated supramolecular liquid crystals (LCs) showing efficient and reversible light-induced LC-to-isotropic phase transitions. Our materials design is based on fluorinated azobenzenes, where the fluorination serves to strengthen the noncovalent interaction with bond-accepting stilbazole molecules, and increase the lifetime of the cis-form of the azobenzene units. The halogen-bonded LCs were characterized by means of X-ray diffraction, hot-stage polarized optical microscopy, and differential scanning calorimetry. Simultaneous analysis of light-induced changes in birefringence, absorption, and optical scattering allowed us to estimate tha…
Halogen bonding stabilizes a cis-azobenzene derivative in the solid state : A crystallographic study
Crystals oftrans- andcis-isomers of a fluorinated azobenzene derivative have been prepared and characterized by single-crystal X-ray diffraction. The presence of F atoms on the aromatic core of the azobenzene increases the lifetime of the metastablecis-isomer, allowing single crystals of thecis-azobenzene to be grown. Structural analysis on thecis-azobenzene, complemented with density functional theory calculations, highlights the active role of the halogen-bond contact (N...I synthon) in promoting the stabilization of thecis-isomer. The presence of a long aliphatic chain on the azobenzene unit induces a phase segregation that stabilizes the molecular arrangement for both thetrans- andcis-i…
Surface-relief gratings in halogen-bonded polymer-azobenzene complexes A concentration-dependence study
In recent years, supramolecular complexes comprising a poly(4-vinylpyridine) backbone and azobenzene-based halogen bond donors have emerged as a promising class of materials for the inscription of light-induced surface-relief gratings (SRGs). The studies up to date have focused on building supramolecular hierarchies, i.e., optimizing the polymer–azobenzene noncovalent interaction for efficient surface patterning. They have been conducted using systems with relatively low azobenzene content, and little is known about the concentration dependence of SRG formation in halogen-bonded polymer–azobenzene complexes. Herein, we bridge this gap, and study the concentration dependence of SRG formation…
Dissecting the packing forces in mixed perfluorocarbon/aromatic co-crystals
We carried out a systematic evaluation of the packing forces in co-crystals featuring monoiodo- and diiodo-perfluoroalkanes and 1,2,4-oxadiazoles through single crystal X-ray diffraction and theoretical analysis. The molecules assemble via a combination of halogen bonding and specific dispersive interactions involving the perfluorinated units. We quantitatively elucidated the nature and strength of such interactions through solid-state calculations and Hirshfeld surface analysis. One of the co-crystals, formed by two monoiodoperfluorodecane molecules, the longest perfluorinated chain ever solved at the atomic level, allowed us to fully highlight the role of fluorous interactions.
Halogen-bonded photoresponsive materials
The aim of the present review is to illustrate to the reader the state of the art on the construction of supramolecular azobenzene-containing materials formed by halogen bonding. These materials include several examples of polymeric, liquid crystalline or crystalline species whose performances are either superior to the corresponding performances of their hydrogen-bonded analogues or simply distinctive of the halogen-bonded species. submittedVersion Peer reviewed
Halogen bond directionality translates tecton geometry into self-assembled architecture geometry
The structures of halogen-bonded infinite chains involving two diiodoperfluoroalkanes and a bent bis(pyrid-4′-yl)oxadiazole show that the geometry of the pyridyl pendant rings is translated into the angle between the formed halogen bonds.
Superfluorinated ionic liquid crystals based on supramolecular, halogen-bonded anions
Unconventional ionic liquid crystals in which the liquid crystallinity is enabled by halogen-bonded supramolecular anions [CnF2 n+1-I⋯I⋯I-CnF2 n+1]- are reported. The material system is unique in many ways, demonstrating for the first time 1) ionic, halogen-bonded liquid crystals, and 2) imidazolium-based ionic liquid crystals in which the occurrence of liquid crystallinity is not driven by the alkyl chains of the cation. Out of the ordinary: The high directionality of halogen bonds and the fluorophobic effect were exploited in the design and synthesis of a new family of unconventional superfluorinated ionic liquid crystals. The liquid crystallinity of the system is driven by halogen-bonded…
Mesogens with Aggregation-Induced Emission Formed by Hydrogen Bonding
In this contribution, we report a supramolecular approach toward mesogens showing aggregation-induced emission (AIE). AIE-active aromatic thioethers, acting as hydrogen-bond donors, were combined with alkoxystilbazoles as hydrogen-bond acceptors. Upon self-assembly, hydrogen-bonded complexes with monotropic liquid crystalline behavior were obtained. In addition, it was found that the introduction of a chiral citronellyl side chain leads to drastic bathochromic shift of the emission, which was not observed for linear alkyl chains. The mesomorphic behavior, as well as the photophysical properties as a solid and in the mesophase of the liquid crystalline assemblies, were studied in detail.
Hydrogen-bonded liquid crystals with broad-range blue phases
We report a modular supramolecular approach for the investigation of chirality induction in hydrogen-bonded liquid crystals. An exceptionally broad blue phase with a temperature range of 25 °C was found, which enabled its structural investigation by solid state 19F-NMR studies and allowed us to report order parameters of the blue phase I for the first time.
Coordination networks incorporating halogen-bond donor sites and azobenzene groups
Two Zn coordination networks, {[Zn(1)(Py)2]2(2-propanol)}n (3) and {[Zn(1)2(Bipy)2](DMF)2}n (4), incorporating halogen-bond (XB) donor sites and azobenzene groups have been synthesized and fully characterized. Obtaining 3 and 4 confirms that it is possible to use a ligand wherein its coordination bond acceptor sites and XB donor sites are on the same molecular scaffold (i.e., an aromatic ring) without interfering with each other. We demonstrate that XBs play a fundamental role in the architectures and properties of the obtained coordination networks. In 3, XBs promote the formation of 2D supramolecular layers, which, by overlapping each other, allow the incorporation of 2-propanol as a gues…
ortho -Fluorination of azophenols increases the mesophase stability of photoresponsive hydrogen-bonded liquid crystals
Photoresponsive liquid crystals (LCs) whose alignment can be controlled with UV-Visible light are appealing for a range of photonic applications. From the perspective of exploring the interplay between the light response and the self-assembly of the molecular components, supramolecular liquid crystals are of particular interest. They allow elaborating the structure-property relationships that govern the optical performance of LC materials by subtle variation of the chemical structures of the building blocks. Herein we present a supramolecular system comprising azophenols and stilbazoles as hydrogen-bond donors and acceptors, respectively, and show that ortho-fluorination of the azophenol dr…
Supramolecular hierarchy among halogen and hydrogen bond donors in light-induced surface patterning
Halogen bonding, a noncovalent interaction possessing several unique features compared to the more familiar hydrogen bonding, is emerging as a powerful tool in functional materials design. Herein, we unambiguously show that one of these characteristic features, namely high directionality, renders halogen bonding the interaction of choice when developing azobenzene-containing supramolecular polymers for light-induced surface patterning. The study is conducted by using an extensive library of azobenzene molecules that differ only in terms of the bond-donor unit. We introduce a new tetrafluorophenol-containing azobenzene photoswitch capable of forming strong hydrogen bonds, and show that an io…
Improving the mesomorphic behaviour of supramolecular liquid crystals by resonance-assisted hydrogen bonding
A systematic structure-property relationship study on hydrogen-bonded liquid crystals was performed, revealing the impact of resonance-assisted hydrogen bonds (RAHBs) on the self-assembling behavior of the supramolecular architecture. The creation of a six-membered intramolecular hydrogen-bonded ring acts as a counterpart to the self-organization between hydrogen bond donators and acceptors and determines thus the suprastructure. Variation of the hydrogen-bonding pattern allowed us to significantly improve the temperature range of the reported liquid crystalline assemblies.
Naturally occurring polyphenols as building blocks for supramolecular liquid crystals – substitution pattern dominates mesomorphism
A modular supramolecular approach towards hydrogen-bonded liquid crystalline assemblies based on naturally occurring polyphenols is reported. The combination of experimental observations, crystallographic studies and semi-empirical analyses of the assemblies provides insight into the structure–property relationships of these materials. Here a direct correlation of the number of donor OH-groups as well as their orientation with the mesomorphic behavior is reported. We discovered that the number and orientation of the OH-groups have a stronger influence on the mesomorphic behavior of the supramolecular assemblies than the connectivity (e.g. stilbenoid or chalconoid) of the hydrogen bond donor…
Photoalignment and Surface-Relief-Grating Formation are Efficiently Combined in Low-Molecular-Weight Halogen-Bonded Complexes
It is demonstrated that halogen bonding can be used to construct low-molecular-weight supramolecular complexes with unique light-responsive properties. In particular, halogen bonding drives the formation of a photoresponsive liquid-crystalline complex between a non-mesogenic halogen bond-donor molecule incorporating an azo group, and a non-mesogenic alkoxystilbazole moiety, acting as a halogen bond-acceptor. Upon irradiation with polarized light, the complex exhibits a high degree of photoinduced anisotropy (order parameter of molecular alignment > 0.5). Moreover, efficient photoinduced surface-relief-grating (SRG) formation occurs upon irradiation with a light interference pattern, with…
Photoresponsive Halogen-Bonded Liquid Crystals: The Role of Aromatic Fluorine Substitution
A new strategy for controlling the liquid crystalline and photophysical properties of supramolecular mesogens assembled via halogen bonding is reported. Changing the degree of fluorination at the halogen-bond donor of the supramolecular liquid crystal allows for the fine-tuning of the halogen bond strength and thereby provides control over the temperature range of the mesophase. At least three fluorine atoms have to be present to ensure efficient polarization of the halogen-bond donor and the formation of a mesophase. In addition, it was found that stilbazole acceptors are superior to their azopyridine counterparts in promoting stable liquid crystalline phases. The halogen-bond-driven supra…
Alkylated Aromatic Thioethers with Aggregation‐Induced Emission Properties—Assembly and Photophysics
In this contribution, we present the synthesis and self-assembly of alkylated thioethers with interesting photophysical properties. To this end, the emission, absorption and excitation spectra in organic solvents and as aggregates in water were measured as well as the corresponding photoluminescence quantum yields and lifetimes. The aggregates in aqueous media were visualized and measured using transmission electron microscopy. Besides that, crystal structures of selected compounds allowed a detailed discussion of the structure–property relationship. Furthermore, the mesomorphic behavior was investigated using polarized optical microscopy (POM) as well as differential scanning calorimetry (…
Supramolecular Modification of ABC Triblock Terpolymers in Confinement Assembly
The self-assembly of AB diblock copolymers in three-dimensional (3D) soft confinement of nanoemulsions has recently become an attractive bottom up route to prepare colloids with controlled inner morphologies. In that regard, ABC triblock terpolymers show a more complex morphological behavior and could thus give access to extensive libraries of multicompartment microparticles. However, knowledge about their self-assembly in confinement is very limited thus far. Here, we investigated the confinement assembly of polystyrene-block-poly(4-vinylpyridine)-block-poly(tert-butyl methacrylate) (PS-b-P4VP-b-PT or SVT) triblock terpolymers in nanoemulsion droplets. Depending on the block weight fractio…
Alkyloxy modified pyrene fluorophores with tunable photophysical and crystalline properties
Novel alkyloxy modified 2,7-di-tert-butyl-4,5,9,10-tetra(arylethynyl)pyrenes were prepared through a straightforward Sonogashira coupling approach. Optical properties such as quantum yields and absorption/emission spectra of the fluorophores were investigated by UV/Vis and fluorescence measurements. Aggregation induced excimer formation of the chromophores in polar solvents and in the solid state was proved by the presence of a characteristic bathochromically shifted emission band and a decrease of the emission capability. These results strongly indicate the unexpected observation that the excimer formation of adjacent pyrene rings is not prevented by the introduction of bulky tert-butyl su…
Structure-property relationships in aromatic thioethers featuring aggregation-induced emission : Solid-state structures and theoretical analysis
We describe in this paper a structure–property relationship study of aromatic thioethers with aggregation-induced emission (AIE) properties. We combine a structural analysis based on geometrical consideration with an in-depth analysis of the crystalline packing supported by quantum mechanical calculations. Our results allow us to correlate the enhanced fluorescence quantum yields with the significant increase of C–H⋯π and the decrease of π⋯π interactions in the solid state – a result which supports the well-accepted AIE mechanism quantitatively.
Photoresponsive ionic liquid crystals assembled: Via halogen bond: En route towards light-controllable ion transporters
We demonstrate that halogen bonding (XB) can offer a novel approach for the construction of photoresponsive ionic liquid crystals. In particular, we assembled two new supramolecular complexes based on 1-ethyl-3-methylimidazolium iodides and azobenzene derivatives containing an iodotetrafluoro-benzene ring as XB donor, where the iodide anion acted as an XB acceptor. DSC and X-ray diffraction analyses revealed that the preferred stoichiometry between the XB donors and acceptors is 2 : 1, and that the iodide anions act as bidentate XB-acceptors, binding two azobenzene derivatives. Due to the high directionality of the XB, calamitic superanions are obtained, while the segregation occurring betw…
Hierarchical Self-Assembly of Halogen-Bonded Block Copolymer Complexes into Upright Cylindrical Domains
Summary Self-assembly of block copolymers into well-defined, ordered arrangements of chemically distinct domains is a reliable strategy for preparing tailored nanostructures. Microphase separation results from the system, minimizing repulsive interactions between dissimilar blocks and maximizing attractive interactions between similar blocks. Supramolecular methods have also achieved this separation by introducing small-molecule additives binding specifically to one block by noncovalent interactions. Here, we use halogen bonding as a supramolecular tool that directs the hierarchical self-assembly of low-molecular-weight perfluorinated molecules and diblock copolymers. Microphase separation …
Supramolecular control of liquid crystals by doping with halogen-bonding dyes
Introducing photochromic or polymeric dopants into nematic liquid crystals is a well-established method to create stimuli-responsive photonic materials with the ability to "control light with light". Herein, we demonstrate a new material design concept by showing that specific supramolecular interactions between the host liquid crystal and the guest dopants enhance the optical performance of the doped liquid crystals. By varying the type and strength of the dopant-host interaction, the phase-transition temperature, the order parameter of the guest molecules, and the diffraction signal in response to interference irradiation, can be accurately engineered. Our concept points out the potential…
Photo-switching and -cyclisation of hydrogen bonded liquid crystals based on resveratrol
A series of hydrogen-bonded liquid crystals based on resveratrol and resveratrone is reported and investigated with respect to their photo-switchability (at 405 nm) and photo-cyclisation (at 300 nm).
Chiral mesophases of hydrogen-bonded liquid crystals
The chiral induction in hydrogen-bonded liquid crystals is investigated. The experimental study was accompanied by detailed density functional theory calculations and variable-temperature solid-state deuteron NMR measurements indicating that interactions between the linking groups of the hydrogen-bond accepting unit play a key role in the chiral induction.
Halogen bonding enhances nonlinear optical response in poled supramolecular polymers
We demonstrate that halogen bonding strongly enhances the nonlinear optical response of poled supramolecular polymer systems. We compare three nonlinear optical chromophores with similar electronic structures but different bond-donating units, and show that both the type and the strength of the noncovalent interaction between the chromophores and the polymer matrix play their own distinctive roles in the optical nonlinearity of the systems. acceptedVersion Peer reviewed
Halogen Bonding beyond Crystals in Materials Science
Halogen bonding has recently gained well deserved attention in present-day research for its importance in many fields of supramolecular science and crystal engineering. Although generally overlooked in comprehensive studies in the past, halogen bonding has become an important tool also in the field of materials science. An increased number of scientific reports are published every year where halogen bonding is exploited in soft materials rather than in crystal engineering. Here, we focus on a description of the most exciting contemporary developments in the field of halogen-bonded functional soft materials, assembled using the guiding principles of crystal engineering. We give a particular …
Azobenzene-based difunctional halogen-bond donor: Towards the engineering of photoresponsive co-crystals
Halogen bonding is emerging as a powerful non-covalent interaction in the context of supramolecular photoresponsive materials design, particularly due to its high directionality. In order to obtain further insight into the solid-state features of halogen-bonded photoactive molecules, three halogen-bonded co-crystals containing an azobenzene-based difunctional halogen-bond donor molecule, (E)-bis(4-iodo-2,3,5,6-tetrafluorophenyl)diazene, C12F8I2N2, have been synthesized and structurally characterized by single-crystal X-ray diffraction. The crystal structure of the non-iodinated homologue (E)-bis(2,3,5,6-tetrafluorophenyl)diazene, C12H2F8N2, is also reported. It is demonstrated that the stud…
CCDC 1445294: Experimental Crystal Structure Determination
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CCDC 1449804: Experimental Crystal Structure Determination
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CCDC 1535157: Experimental Crystal Structure Determination
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CCDC 1866422: Experimental Crystal Structure Determination
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CCDC 1894901: Experimental Crystal Structure Determination
Related Article: Marco Saccone, Steffen Riebe, Jacqueline Stelzer, Christoph Wölper, Constantin G. Daniliuc, Jens Voskuhl, Michael Giese|2019|CrystEngComm|21|3097|doi:10.1039/C9CE00444K
CCDC 1541305: Experimental Crystal Structure Determination
Related Article: Marco Saccone, Francisco Fernandez Palacio, Gabriella Cavallo, Valentina Dichiarante, Matti Virkki, Giancarlo Terraneo, Arri Priimagi, Pierangelo Metrangolo|2017|Faraday Discuss.|203|407|doi:10.1039/C7FD00120G
CCDC 1541306: Experimental Crystal Structure Determination
Related Article: Marco Saccone, Francisco Fernandez Palacio, Gabriella Cavallo, Valentina Dichiarante, Matti Virkki, Giancarlo Terraneo, Arri Priimagi, Pierangelo Metrangolo|2017|Faraday Discuss.|203|407|doi:10.1039/C7FD00120G
CCDC 1446403: Experimental Crystal Structure Determination
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CCDC 1939466: Experimental Crystal Structure Determination
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CCDC 1893331: Experimental Crystal Structure Determination
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CCDC 1895359: Experimental Crystal Structure Determination
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CCDC 1886744: Experimental Crystal Structure Determination
Related Article: Marco Saccone, Michael Pfletscher, Sven Kather, Christoph Wölper, Constantin Daniliuc, Markus Mezger, Michael Giese|2019|J.Mater.Chem.C|7|8643|doi:10.1039/C9TC02787D
CCDC 883070: Experimental Crystal Structure Determination
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CCDC 1895646: Experimental Crystal Structure Determination
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CCDC 1939467: Experimental Crystal Structure Determination
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CCDC 1445292: Experimental Crystal Structure Determination
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CCDC 1895424: Experimental Crystal Structure Determination
Related Article: Marco Saccone, Steffen Riebe, Jacqueline Stelzer, Christoph Wölper, Constantin G. Daniliuc, Jens Voskuhl, Michael Giese|2019|CrystEngComm|21|3097|doi:10.1039/C9CE00444K
CCDC 1866421: Experimental Crystal Structure Determination
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CCDC 1025655: Experimental Crystal Structure Determination
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CCDC 1942435: Experimental Crystal Structure Determination
Related Article: Jan Balszuweit, Meik Blanke, Marco Saccone, Markus Mezger, Constantin G. Daniliuc, Christoph Wölper, Michael Giese, Jens Voskuhl|2021|MSDE|6|390|doi:10.1039/D0ME00171F
CCDC 1445293: Experimental Crystal Structure Determination
Related Article: Francisco Fernandez-Palacio, Marco Saccone, Arri Priimagi, Giancarlo Terraneo, Tullio Pilati, Pierangelo Metrangolo, Giuseppe Resnati|2016|CrystEngComm|18|2251|doi:10.1039/C6CE00059B
CCDC 1895645: Experimental Crystal Structure Determination
Related Article: Andreas Kapf, Hassan Eslahi, Meik Blanke, Marco Saccone, Michael Giese, Marcel Albrecht|2019|New J.Chem.|43|6361|doi:10.1039/C9NJ00652D
CCDC 1877494: Experimental Crystal Structure Determination
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CCDC 1871602: Experimental Crystal Structure Determination
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CCDC 1025656: Experimental Crystal Structure Determination
Related Article: Marco Saccone, Valentina Dichiarante, Alessandra Forni, Alexis Goulet-Hanssens, Gabriella Cavallo, Jaana Vapaavuori, Giancarlo Terraneo, Christopher J. Barrett, Giuseppe Resnati, Pierangelo Metrangolo, Arri Priimagi|2015|J.Mater.Chem.C|3|759|doi:10.1039/C4TC02315C
CCDC 2077920: Experimental Crystal Structure Determination
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CCDC 1886743: Experimental Crystal Structure Determination
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CCDC 1945777: Experimental Crystal Structure Determination
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CCDC 1871491: Experimental Crystal Structure Determination
Related Article: Steffen Riebe, Marco Saccone, Jacqueline Stelzer, Andrea Sowa, Christoph Wölper, Kateryna Soloviova, Cristian A. Strassert, Michael Giese, Jens Voskuhl|2019|Chem.Asian J.|14|814|doi:10.1002/asia.201801564
CCDC 1938656: Experimental Crystal Structure Determination
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CCDC 1866420: Experimental Crystal Structure Determination
Related Article: Marco Saccone, Matthias Spengler, Michael Pfletscher, Kim Kuntze, Matti Virkki, Christoph Wölper, Robert Gehrke, Georg Jansen, Pierangelo Metrangolo, Arri Priimagi, Michael Giese|2019|Chem.Mater.|31|462|doi:10.1021/acs.chemmater.8b04197
CCDC 1895360: Experimental Crystal Structure Determination
Related Article: Marco Saccone, Steffen Riebe, Jacqueline Stelzer, Christoph Wölper, Constantin G. Daniliuc, Jens Voskuhl, Michael Giese|2019|CrystEngComm|21|3097|doi:10.1039/C9CE00444K
CCDC 1449805: Experimental Crystal Structure Determination
Related Article: Francisco Fernandez-Palacio, Mikko Poutanen, Marco Saccone, Antti Siiskonen, Giancarlo Terraneo, Giuseppe Resnati, Olli Ikkala, Pierangelo Metrangolo, and Arri Priimagi|2016|Chem.Mater.|28|8314|doi:10.1021/acs.chemmater.6b03460
CCDC 1449802: Experimental Crystal Structure Determination
Related Article: Francisco Fernandez-Palacio, Mikko Poutanen, Marco Saccone, Antti Siiskonen, Giancarlo Terraneo, Giuseppe Resnati, Olli Ikkala, Pierangelo Metrangolo, and Arri Priimagi|2016|Chem.Mater.|28|8314|doi:10.1021/acs.chemmater.6b03460
CCDC 1884535: Experimental Crystal Structure Determination
Related Article: Marco Saccone, Michael Pfletscher, Sven Kather, Christoph Wölper, Constantin Daniliuc, Markus Mezger, Michael Giese|2019|J.Mater.Chem.C|7|8643|doi:10.1039/C9TC02787D