An X-ray structural study of 3-tricyanovinyl-N-methylcarbazole

Popova, E. G.; Chetkina, L. A.; Kotov, B. V.

doi:10.1007/bf00745199

Cited by 2 publications

(3 citation statements)

References 2 publications

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“…For compound 1, two different crystalline structures have been reported. 10,18 The detailed crystallographic data of 2-5 can be found in Table S1-S4 † in the ESI. Molecules 1-5 adopt an almost planar conformation independently of the length of the N-alkyl chain ( Fig.…”

Section: Single-crystal X-ray Analysesmentioning

confidence: 99%

Solid-state organization of n-type carbazole-based semiconductors for organic thin-film transistors

Reig

Puigdollers

Velasco

2018

Phys. Chem. Chem. Phys.

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The development of new organic semiconductors has been mainly led by the search for new π-conjugated cores, but recently the use of flexible side chains is attracting more and more attention to control the molecular packing and order in the solid state to improve the charge-transporting properties. In this work, the charge transport properties of a series of tricyanovinyl-substituted carbazole-based materials with different alkyl chain lengths have been investigated and correlated with the respective intermolecular interactions and molecular packings via X-ray diffraction (XRD) studies.

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Section: Single-crystal X-ray Analysesmentioning

confidence: 99%

Solid-state organization of n-type carbazole-based semiconductors for organic thin-film transistors

Reig

Puigdollers

Velasco

2018

Phys. Chem. Chem. Phys.

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“…Although the compounds herein are known, to the best of our knowledge, none of the structures in the current work have been reported except for compound 1 whose structure was reported in a conference paper and a brief report in 1975 and 1979, respectively, with rather limited details . The authors described two polymorphs . However, despite many crystallization experiments from different solvents and by sublimation, we were able to obtain only one polymorph (the orthorhombic form).…”

Section: Resultsmentioning

confidence: 72%

“… 20 The authors described two polymorphs. 21 However, despite many crystallization experiments from different solvents and by sublimation, we were able to obtain only one polymorph (the orthorhombic form). We point out the slightly different values for the unit cell axes we obtained compared to those reported earlier in [square brackets], a = 11.154; [11.335]; b = 14.604; [14.603]; c = 21.685; [21.731] Å (CYVTPA; CYVTPA01).…”

Section: Resultsmentioning

confidence: 89%

Di- and Tricyanovinyl-Substituted Triphenylamines: Structural and Computational Studies

Pham,

Bader

2024

ACS Omega

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We report herein on the solid-state structures of three closely related triphenylamine derivatives endowed with tricyanovinyl (TCV) and dicyanovinyl (DCV) groups. The molecules described contain structural features commonly found in the design of functional organic materials, especially donor−acceptor molecular and polymeric architectures. The common feature noticeable in these structures is the impact of these exceptionally strong electron-accepting groups in forcing partial planarity of the portion of the molecule carrying these groups and directing the molecular packing in the solid state, resulting in the formation of πstacks of dimers within the unit cell of each. Stacks are formed between phenyl groups bearing electron-accepting groups on two adjacent molecules. Short π−π stack distances ranging from 3.283 to 3.671 Å were observed. Such motif patterns are thought to be conducive for better charge transport in organic semiconductors and enhanced device performance. Intramolecular charge transfer is evident from the shortening of the observed experimental bond lengths in all three compounds. The nitrogen atoms (of the cyano groups) have been shown to be extensively involved in short contacts in all three structures, primarily through C−H•••NC interactions with distances as short as 2.462 Å. The compounds reported here are (3,3-dicyano-2-(4-(diphenylamino)phenyl)-1λ 3allylidene)amide or tricyanovinyltriphenylamine, Ph 3 NTCV (1); 2-(4-(diphenylamino)benzylidene)-malononitrile or dicyanovinyltriphenylamine, Ph 3 NDCV (2); and (3,3-dicyano-2-(4-(di-p-tolylamino)phenyl)-1λ 3 -allylidene)amide or dimethyltricyanovinyltriphenylamine, Me 2 Ph 3 NTCV (3). Results of density functional theory calculations using p) indicate the lowering of LUMO levels as a result of the introduction of these groups with band gaps of 3.13, 2.61, and 2.55 eV for compounds 1− 3, respectively, compared with 4.65 eV calculated for triphenylamine. This is supported by the electronic and fluorescence spectra of these molecules with absorption λ max of 483, 515, and 545 nm for compounds 1, 2, and 3, respectively.

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An X-ray structural study of 3-tricyanovinyl-N-methylcarbazole

Cited by 2 publications

References 2 publications

Solid-state organization of n-type carbazole-based semiconductors for organic thin-film transistors

Solid-state organization of n-type carbazole-based semiconductors for organic thin-film transistors

Di- and Tricyanovinyl-Substituted Triphenylamines: Structural and Computational Studies

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