Molecular Assemblies of Tetrahedral Triphenylmethanol and Triphenylamine Derivatives Bearing −NHCOCnH2n+1 Chains

Akahane, Satoru; Takeda, Takashi; Hoshino, Norihisa; Akutagawa, Tomoyuki

doi:10.1021/acs.cgd.8b01152

Cited by 4 publications

(3 citation statements)

References 52 publications

(68 reference statements)

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“…This holds for compounds with thioamides as well (unpublished), the only difference being higher achievable remnant polarizations due to a larger dipole moment of thioamides ~5.1 D compared to ~4 D of amides. The absence of a ferroelectric signal in a nonplanar triphenylamine-cored trisamide, which showed neither liquid-crystal phases nor dielectric anomaly 152 , and in non-planar tetraphenyl-ethylene (TPE)-cored 153 as well as tetra [2,3]thienylene-cored 154 tetraamides supports the hypothesis (Fig. 35).…”

Section: Amidesmentioning

confidence: 60%

Multifunctional Supramolecular Organic Ferroelectrics

Urbanavičiūtė

2019

Linköping Studies in Science and Technology. Dissertations

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Ferroelectric materials are known and valued for their multifunctionality arising from the possibility to perturb the remnant ferroelectric polarization by electric field, temperature and/or mechanical stimuli. While inorganic ferroelectrics dominate the current market, their organic counterparts may provide highly desired properties like eco-friendliness, easy-processability and flexibility, concomitantly opening unique opportunities to combine multiple functionalities into a single compound that facilitates unprecedented device concepts and designs. Supramolecular organic ferroelectrics of columnar discotic type, that are the topic of this thesis, offer additional advantages related to their strong hierarchical self-assembly and easy tunability by molecular structure modifications, allowing optimization of ferroelectric characteristics and their hybridization with, e.g., semiconductivity. This not only leads to textbook ferroelectric materials that can be used as model systems to understand the general behaviour of ferroics, but also gives rise to previously unobserved effects stemming from the interplay of different functionalities.

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Section: Amidesmentioning

confidence: 60%

Multifunctional Supramolecular Organic Ferroelectrics

Urbanavičiūtė

2019

Linköping Studies in Science and Technology. Dissertations

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“…There are no significant close interactions within the unit cell of triphenylamine except for C–H···π with a relatively long distance (2.817 Å). We also note that there have been several recent structural reports on triphenylamine derivatives, − with various structural features including multicyanoderivatives …”

Section: Resultsmentioning

confidence: 83%

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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“…The crystal structure of triphenylamine is known and has been examined several times (Martin et al, 2007;Sobolev et al, 1985;Howells et al, 1954) There are no significant close interactions within the unit cell of triphenylamine except for C-H� � �� with a relatively long distance (2.817A ˚). We also note that there have been several recent structural reports on triphenylamine derivatives, with various structural features including multicyanoderivatives (Ishi et al, 2019;Akahane et al, 2018;Hariharan et al, 2017;Song et al, 2006;Tang et al, 2010).…”

Section: Structural Commentarymentioning

confidence: 84%

Crystal structure of 1-{4-[bis(4-methylphenyl)amino]phenyl}ethene-1,2,2-tricarbonitrile

Bader,

Pham

2024

Acta Cryst E

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The title compound, C25H18N4, crystallizes in the centrosymmetric orthorhombic space group Pbca, with eight molecules in the unit cell. The main feature noticeable in the structure is the impact of the tricyanovinyl (TCV) group in forcing partial planarity of the portion of the molecule carrying the TCV group and directing the molecular packing in the solid state, resulting in the formation of π-stacks of dimers within the unit cell. Short π–π stack closest atom-to-atom distances of 3.444 (15) Å are observed. Such motif patterns are favorable as they are thought to be conducive for better charge transport in organic semiconductors, which results in enhanced device performance. Intramolecular charge transfer is evident from the shortening in the observed experimental bond lengths. The nitrogen atoms (of the cyano groups) are involved in extensive short contacts, primarily through C—H...NC interactions with distances of 2.637 (17) Å.

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Molecular Assemblies of Tetrahedral Triphenylmethanol and Triphenylamine Derivatives Bearing −NHCOC_nH_2n+1 Chains

Cited by 4 publications

References 52 publications

Multifunctional Supramolecular Organic Ferroelectrics

Multifunctional Supramolecular Organic Ferroelectrics

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

Crystal structure of 1-{4-[bis(4-methylphenyl)amino]phenyl}ethene-1,2,2-tricarbonitrile

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