69079-52-3Relevant articles and documents
Synthesis of triphenylene and dibenzopyrene derivatives: Vanadium oxytrichloride a novel reagent
Kumar,Varshney
, p. 305 - 311 (2001)
This paper presents an efficient synthetic procedure for the preparation of various triphenylene and dibenzopyrene derivatives using VOC13 as a novel reagent. Symmetrically substituted hexaalkoxytriphenylenes are obtained from o-dialkoxybenzenes by oxidative trimerization with VOC13 in high yields. The oxidative coupling of a 3,3′,4,4′-tetraalkoxybiphenyl and 1,2-dialkoxybenzenes or 1,2,3-trialkoxybenzenes affords unsymmetrically substituted derivatives of triphenylene. The reagent oxidizes 3,3′,4,4′-tetraalkoxybiphenyl efficiently to 2,5,6,9,12,13-hexaalkoxydibenzo[fg, op]naphthacene-1,8-quinone and its 1,10-quinone isomer. Both the quinones can be converted to liquid crystalline derivatives using well-established chemistry. Effects of solvent, reagent concentration, acid catalyst and temperature have been studied.
Influence of disorder on electronic excited states: An experimental and numerical study of alkylthiotriphenylene columnar phases
Marguet, Sylvie,Markovitsi, Dimitra,Millié, Philippe,Sigal, Hervé,Kumar, Sandeep
, p. 4697 - 4710 (1998)
The spectroscopic properties of discotic hexa-alkylthiotriphenylenes are studied in solution and thin films and compared to those of hexa-alkyloxytriphenylenes. The solution properties are analyzed in the light of CS-INDO-CIPSI quantum chemistry calculations. The absorption maximum is assigned to the degenerate S0 → S4 transition. The fluorescence of the neat phases is attributed to weakly bound excimers. The phase transition leading from ordered to disordered columnar stacks induces an increase in the oscillator strength of the S0 → S1 transition and favors excimer formation. The influence of structural disorder on the properties of the delocalized states is rationalized by using various approximations within the frame of the exciton theory; three models for the calculation of the exciton coupling (point dipole, extended dipole, atomic transition charge distribution) are tested, short and long range interactions are considered, and the introduction of a dielectric constant is discussed. The best agreement between experimental and calculated absorption maxima is obtained using the atomic charge transition model. Off-diagonal disorder is correlated to structural disorder by changing the orientation and the position of the molecules within the aggregate. The case of degenerate molecular states is compared to that of nondegenerate ones. Orientational disorder has a dramatic effect on the energy and the localization of the upper eigenstate when molecular states are nondegenerate. Conversely, the properties of degenerate eigenstates are quite insensitive to orientational disorder. The magnitude of the off-diagonal disorder induced by positional disorder largely depends on the model used in the calculation of the exciton coupling. The results of the numerical calculations are in agreement with the small change observed in the neat phases absorption maxima upon a quasi one-dimensional melting of columnar stacks.
A high yield easy method for the preparation of alkoxy-substituted triphenylenes
Naarmann,Hanack,Mattmer
, p. 477 - 478 (1994)
2,3,6,7,10,11-Hexamethoxytriphenylene is prepared by oxidative trimerization of 1,2-dimethoxybenzene (veratrol) with iron(III) chloride/sulfuric acid in nearly quantitative yield. The obtained crude product is almost pure. Other alkoxy-substituted triphenylenes are also synthesized by this method.
Molecular Structure and Donor–Acceptor Properties of β-(2,4,7-Trinitro-9-fluorenylideneaminooxy)propionic Acid Complexes with Triphenylene-Containing Systems
Bondarenko, G. N.,Legkov, S. A.,Merekalov, A. S.,Otmakhova, O. A.,Talroze, R. V.
, p. 347 - 362 (2022/03/17)
Abstract: Quantum chemical calculations and FTIR spectroscopic studies show that β-(2,4,7-trinitro-9-fluorenylideneiminooxy)propionic acid (TNF-carb) can act as an electron acceptor. It stabilizes charge transfer complexes with discotic triphenylene-conta
Highly ordered columnar superlattice nanostructures with improved charge carrier mobility by thermotropic self-assembly of triphenylene-based discotics
Bi, Jingze,Wu, Hao,Zhang, Zhenhu,Zhang, Ao,Yang, Huanzhi,Feng, Yuwen,Fang, Yi,Zhang, Lina,Wang, Zhengran,Qu, Wentao,Liu, Feng,Zhang, Chunxiu
, p. 12463 - 12469 (2019/10/28)
A series of triphenylene esters with two ester groups at 2,3-, 2,7-, 2,6- and 3,6- substituent positions was successfully synthesized and fully investigated. Their self-assembly properties were exhaustively examined by DSC, POM, 1DXRD, 2DXRD, SAXS, TEM methods together with EDM and ESP calculations. It was unexpected that the 3,6-substituted triphenylene ester T5E36 formed an uncommonly helical hexagonal columnar superlattice structure made up of 91 right-handed helixes with a pitch of 60.3 ?. This helical superlattice structure was further studied by using transmission electron microscopy and the diameter of the T5E36 particles was found to be at the nanometer scale. Ultimately, the bipolar charge carrier mobility was measured by the time-of-flight method to be in the order of 10-1 cm2 V-1 s-1. The formation of this helical superlattice nanostructure no doubt improved their electronic properties and made them more attractive in organic electronics.
