A Donor–Acceptor–Donor Structured Organic Conductor with S···S Chalcogen Bonding

Bai, Monalisa; Thomas, Sajesh P.; Kottokkaran, Ranjith; Nayak, Susanta K.; Ramamurthy, Praveen C.; Row, Tayur N. Guru

doi:10.1021/cg401069y

Cited by 65 publications

(53 citation statements)

References 62 publications

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“…magnitude smaller than the corresponding value in the BCP associated with the S•••S contact in the S--S_lat(HT) interaction. It is worth mentioning that the computed values of the electronic density in the BCPs associated with the S•••S contacts of HT and the shorter S•••S contacts of LT are very similar to the experimental value determined for the S•••S contacts in TiS2 77 and the computed values for other organic crystals featuring S•••S chalcogen interactions 78,79. …”

supporting

confidence: 80%

Reorganization of Intermolecular Interactions in the Polymorphic Phase Transition of a Prototypical Dithiazolyl-Based Bistable Material

Francese

Mota

Deumal

et al. 2019

Crystal Growth & Design

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The spin transitions undergone by several molecular crystals of dithiazolyl (DTA) radicals make this type of radicals promising candidates for future sensors and memory devices. Here, we present a systematic computational study of the intermolecular interactions existing in the two polymorphs of the neutral radical 1,3,5-trithia-2,4,6-triazapentalenyl in order to elucidate the origin of the difference in energy between those two polymorphs involved in its spin transition and to understand the crystal packing of this prototype of bistable materials. The π-π interactions between radicals are the main driving force for the crystal packing of both polymorphs, which comprises π-stacks of radicals. Among the interstack interactions, the strongest ones are those mediated by six-and four-center S•••N bridges. The difference in energy between polymorphs, in turn, is mainly controlled also by the intrastack π-π intermolecular interactions, and the interstack S•••S contacts instead of the S•••N contacts. Since the supramolecular motifs herein identified as important for the crystal packing and/or for the energy difference between polymorphs (and, thus, for the spin transition temperature) are common to other members of the DTA family, our results provide valuable information to understand better the structure and properties of other switchable DTA-based materials.

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supporting

confidence: 80%

Reorganization of Intermolecular Interactions in the Polymorphic Phase Transition of a Prototypical Dithiazolyl-Based Bistable Material

Francese

Mota

Deumal

et al. 2019

Crystal Growth & Design

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“…22,23 The S … S interaction is also one of the major forces that influence the structures of organic conductors. 24,25 Namely, S … S interactions are responsible for the molecular structures and functions of many well-known examples of organic conducting materials such as different derivates of tetrathiofulvalene (TTF). In these structures S … S interactions support the supramolecular assembly in the absence of any strong hydrogen bonding interactions.…”

Section: Introductionmentioning

confidence: 99%

Preferred Geometries and Energies of Sulfur–Sulfur Interactions in Crystal Structures

Antonijević

Janjić

Milčić

et al. 2016

Crystal Growth & Design

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It has been demonstrated that sulfur-sulfur interactions can exist in various molecular systems. In this work we investigated sulfur-sulfur interactions in crystal structures of small molecules by analyzing geometric data from the Cambridge Structural Database (CSD) and by quantum chemical calculations. The analysis of cysteine residues (R-CH 2 SH) in the crystal structures from the CSD indicates that in the sulfur-sulfur interactions the preferred is parallel orientation of two C-S-H planes. Quantum chemical calculations were performed on model systems of methanethiol dimers. The most stable geometry of methanethiol dimer with parallel orientation of C-S-H planes is significantly strong; the interaction energy is -1.80 kcal/mol calculated at the very accurate CCSD(T)/CBS level. However, the strongest sulfur-sulfur Author Contributions: I.S.A. performed quantum chemical calculations, interpreted the data, and prepared the manuscript.; G.V.J. proposed topic and performed CSD search.; M.K.M. has done SAPT, QTAIM and NCI index method calculations and analyzed data.; S.D.Z. analyzed the results, supervised, wrote and edited the manuscript.

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“…For the next three solvents used; CF, THF and 12DCE, formation of spikes on spheres with variation in spike size and shape of spheres are observed. 34 There are two peaks in between 8.5 -9°, at 8.6° and 8.75°. Solvents from acetone to 12DCE have poor to partial solubility, leaving the crystallites as such by just forming spheres due to rapid solvent evaporation.…”

Section: Rsc Advances Accepted Manuscriptmentioning

confidence: 98%

“…30,31 In the current work, effect of various solvents, their solubilities and rate of evaporation at ambient temperature, on the morphology of conducting organic molecule when electrosprayed is evaluated. 34 It was also blended with poly (ethylene oxide) obtaining electrospun nanofibers of barb wires architecture. It has been studied for feasibility in OPVs via spincoating technique in poly DAD form with [6,6]-Phenyl-C61-Butyric Acid Methyl Ester (PCBM) using chlorobenzene as solvent 32 and as poly (3-hexyl thiophene):DTCPA composites using chloroform as solvent.…”

Section: Introductionmentioning

confidence: 99%

Design and morphology control of a thiophene derivative through electrospraying using various solvents

Khanum

Ramamurthy

2015

RSC Adv.

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In the present work, electrospraying of an organic molecule is carried out using various solvents, obtaining fibril structures along with a range of distinct morphologies. Solvent characteristics play a major role in achieving the morphology of the organic material. A thiophene derivative (7, 9-di (thiophen-2-yl)-8H-cyclopenta[a]acenaphthylen-8-one) (DTCPA) of donor-acceptordonor (DAD) architecture is used to study this solvent effect. Seven solvents with decreasing vapour pressure are selected for experiments. Electrospraying is conducted at a solution concentration of 1.5 wt % and a constant applied voltage of 15 kV. Gradual transformation in morphology of the electrospun product from spikes-sphere to only spikes is observed. A mechanism describing this transformation is proposed based on the electron micrograph analysis and XRD analysis. These data indicate that the morphological change is due to the synergistic effect of both vapour pressure and dielectric constant of the solvents. Through a reasonable control over the crystallites size and morphology along with supporting transformation mechanism theory, this study elucidates electrospraying as a prospective method for designing the architectures in organic electronics.

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A Donor–Acceptor–Donor Structured Organic Conductor with S···S Chalcogen Bonding

Cited by 65 publications

References 62 publications

Reorganization of Intermolecular Interactions in the Polymorphic Phase Transition of a Prototypical Dithiazolyl-Based Bistable Material

Reorganization of Intermolecular Interactions in the Polymorphic Phase Transition of a Prototypical Dithiazolyl-Based Bistable Material

Preferred Geometries and Energies of Sulfur–Sulfur Interactions in Crystal Structures

Design and morphology control of a thiophene derivative through electrospraying using various solvents

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