Halogen‐Bond Effects on the Thermo‐ and Photochromic Behaviour of Anil‐Based Molecular Co‐crystals

Carletta, Andrea; Spinelli, Floriana; D’Agostino, Simone; Ventura, Barbara; Chierotti, Michele R.; Gobetto, Roberto; Wouters, Johan; Grepioni, Fabrizia

doi:10.1002/chem.201605953

Cited by 58 publications

(68 citation statements)

References 81 publications

(209 reference statements)

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“…Therefore, cocrystallization is a potential candidate for tunable optical properties. Also, it has been discovered that the optical behaviors of individual components may be altered in cocrystal systems through synergistic effects . Guldi's group has developed a series of cocrystal nanosheets, wherein C 70 and (metallo)porphyrins act as acceptor and donors, respectively.…”

Section: Functionality‐related Fundamental Principles Of Organic Cocrmentioning

confidence: 99%

Cocrystal Engineering: A Collaborative Strategy toward Functional Materials

et al. 2019

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materials, [9][10][11][12] which are crystalline singlephase materials composed of two or more different compounds generally in a stoichiometric ratio, [13] providing a platform for unveiling the structure-property relationships at a molecular level. [14] The building blocks are assembled via noncovalent interactions, offering the opportunity to achieve noncovalent synthesis of functional molecules. [15] Compared with the traditional covalent synthesis, cocrystal engineering offers numerous advantages, including: 1) avoiding complicated synthesis procedures, and cocrystal assemblies have been successfully fabricated by the vapor methods and solution-processing methods in a facile and low-cost way; 2) manipulating intermolecular interactions through selecting suitable conformers from a plentiful supply of raw materials, resulting in tunable structures, morphologies, and sizes; 3) achieving rare and multifunctional properties through a collaborative strategy in distinct constituent units, which are difficult to realize for individual components. [16][17][18] Cocrystal engineering began to draw much attention since the exploration of the metal conductive tetrathiafulvalene-7,7,8,8-tetracyanoquinodimethane (TTF-TCNQ) cocrystals in 1973. [19] The peculiar conductivity in organic materials makes it possible for cocrystals to serve as organic electrodes, which can effectively lower the contact resistance and further improve device performance. Encouraged by this, cocrystals can serve as a breakthrough and provide an opportunity to discover novel physicochemical properties, which are far beyond the performance of single materials. In this respect, dielectric response [20] and nonlinear optics [21,22] are also realized through rational design of each component, which is absent in their constitute components. Even more, the bottom-up supramolecular assembly provides the opportunity to equip them with the individual properties of the donor or acceptor to create multifunctional materials. [23] Typically, ambipolar charge transport can be generated by coassembling p-type semiconductors and n-type ones, and the charge-carrier mobility is now up to 1.57 cm 2 V −1 s −1 for holes and 0.47 cm 2 V −1 s −1 for electrons. [24] To date, these exciting results accelerate the investigations of organic functional cocrystals, such as room-temperature ferroelectricity, [25][26][27] optical waveguide properties, [28,29] pure organic room-temperature phosphorescent properties, [30][31][32] stimulusresponse (e.g., mechanical stress, [33,34] heat, [35,36] or solvent [37] ) characteristics, photovoltaics, [38] and near-infrared photothermal (PT) conversion and imaging, [39] etc.Cocrystal engineering with a noncovalent assembly feature by simple constituent units has inspired great interest and has emerged as an efficient and versatile route to construct functional materials, especially for the fabrication of novel and multifunctional materials, due to the collaborative strategy in the distinct constituent units. Meanwhile, the precise crystal a...

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Section: Functionality‐related Fundamental Principles Of Organic Cocrmentioning

confidence: 99%

Cocrystal Engineering: A Collaborative Strategy toward Functional Materials

et al. 2019

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“…Chiroptical molecular switches that show directional motion are prototypical synthetic molecular motors . They have been incorporated into a nanocar model, immobilized on solid surfaces, or applied as asymmetric catalysts …”

Section: Molecular Photoswitchesmentioning

confidence: 99%

Recent Implementations of Molecular Photoswitches into Smart Materials and Biological Systems

Pianowski

2019

Chemistry A European J

285

226

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Light is a nearly ideal stimulus for molecular systems. It delivers information encoded in the form of wavelengths and their intensities with high precision in space and time. Light is a mild trigger that does not permanently contaminate targeted samples. Its energy can be reversibly transformed into molecular motion, polarity, or flexibility changes. This leads to sophisticated functions at the supramolecular and macroscopic levels, from light‐triggered nanomaterials to photocontrol over biological systems. New methods and molecular adapters of light are reported almost daily. Recently reported applications of photoresponsive systems, particularly azobenzenes, spiropyrans, diarylethenes, and indigoids, for smart materials and photocontrol of biological setups are described herein with the aim to demonstrate that the 21st century has become the Age of Enlightenment—“Le siècle des Lumières”—in molecular sciences.

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“…[28] Among the advantages of mechanosynthesis are:l arge quantitieso fs tarting materials can be used, timesaving properties, and the possibility to reduce side reactions, af actor that can lead to higher yields and better conversions. [28,29] Furthermore, mechanosynthesis has been successfully employed in co-crystal synthesis [30][31][32] and polymorph selection, [33] allowing the generation of solid forms that are otherwise not accessible. Sonosynthesis (also called ultrasound-assisted synthesis) has been widely used in the synthesis of graphene-based materials and in the catalyst-frees ynthesis of av ariety of organicc ompounds.…”

Section: Introductionmentioning

confidence: 99%

Direct Access by Mechanochemistry or Sonochemistry to Protonated Merocyanines: Components of a Four‐State Molecular Switch

Colaço¹,

Carletta

Gysel

et al. 2018

ChemistryOpen

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Direct access to the protonated merocyanine forms of two substituted spiropyrans by mechanosynthesis or sonochemistry was explored. The compounds were formed by the condensation reaction of the methyleneindolium iodide salt with salicylaldehyde derivatives. X‐ray crystallography, 1H NMR spectroscopy, ab initio geometry optimization, and absorption spectroscopy were combined to provide a better understanding of the four‐state molecular switch system in which the newly synthesized protonated merocyanines were found to play a central role. The results of this study suggest that the stability of the protonated merocyanines requires acidic conditions, as treatment with base led to the corresponding unprotonated merocyanines, which in turn spontaneously converted into photochromic closed spiropyrans.

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Halogen‐Bond Effects on the Thermo‐ and Photochromic Behaviour of Anil‐Based Molecular Co‐crystals

Cited by 58 publications

References 81 publications

Cocrystal Engineering: A Collaborative Strategy toward Functional Materials

Cocrystal Engineering: A Collaborative Strategy toward Functional Materials

Recent Implementations of Molecular Photoswitches into Smart Materials and Biological Systems

Direct Access by Mechanochemistry or Sonochemistry to Protonated Merocyanines: Components of a Four‐State Molecular Switch

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