69079-52-3Relevant academic research and scientific papers
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.
Synthesis of hexa-alkyloxytriphenylenes using FeCl3 supported on alumina
Cooke, Graeme,Sage, Valerie,Richomme, Tanguy
, p. 1767 - 1771 (1999)
Several symmetrical and unsymmetrical hexa-alkyloxytriphenylenes have been synthesised in good yield from diakyloxy benzenes and terphenyl derivatives using FeCl3 supported on alumina.
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.
Triphenylene Columnar Liquid Crystals: Excited States and Energy Transfer
Markovitsi, Dimitra,Germain, Arnaud,Millie, Philippe,Lecuyer, Pierre,Gallos, Lazaros K.,at al.
, p. 1005 - 1017 (1995)
The present paper deals with the photophysical properties of columnar liquid crystals formed by hexakis(alkyloxy)triphenylenes.Absorption and fluorecence spectra of solutions are analyzed on the basis of quantum chemical calculations performed by the CS-INDO-CI (conformations spectra-intermediate neglect of differential overlap-configuration interaction) method: the absorption maximum is due to the S0->S4 transition while fluorescence originates from the weak S0->S1 transition.In columnar aggregates, the former transition corresponds to delocalized excited states while the latter corresponds to localised ones; calculation of intermolecular interactions shows that, at the temperature domain of the mesophases, all the molecules have the same excitation energy and, therefore, no spectral diffusion of the fluorescence is expected, in agreement with the time-resolved emission spectra.Excitation transfer is investigated by studying the fluorescence decays of mesophases doped with energy traps.Their analysis is made by means of Monte Carlo simulations considering both intracolumnar and intercolumnar jumps and using four different models for the distance dependence of the hopping probability.The best description is obtained with a model based on the extended dipole approximation and taking into account molecular orientation.
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.
Facile transformation of 1-aryltriphenylenes into dibenzo[fg,op]tetracenes by intramolecular Scholl cyclodehydrogenation: synthesis, self-assembly, and charge carrier mobility of large π-extended discogens
Zhao, Ke-Qing,Jing, Min,An, Ling-Ling,Du, Jun-Qi,Wang, Yan-Hong,Hu, Ping,Wang, Bi-Qin,Monobe, Hirosato,Heinrich, Beno?t,Donnio, Bertrand
, p. 669 - 682 (2017)
The search for new organic semiconductors with enhanced charge transport properties and self-organizing abilities plays a pivotal role in the development of new applications in the emerging field of organic electronics. We have synthesized two series of d
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
New complexes of liquid crystal discotic triphenylenes: Induction of the double gyroid phase
Bondarenko, G. N.,Ivanov, D. A.,Maryasevskaya, A. V.,Merekalov, A. S.,Otmakhova, O. A.,Piryazev, A. A.,Shandryuk, G. A.,Talroze, R. V.
, p. 16827 - 16836 (2021/08/20)
Electron donor-acceptor liquid crystals have been attracting considerable attention due to possible applications in optoelectronics and photonics. The creation of such charge transfer complexes is a powerful and flexible instrument for modifying the structures and properties compared to those of the initial components. In the present work, such an approach is exemplified on new complexes formed via non-covalent interactions of triphenylene discotics, namely, 2,3,6,7,10,11-hexakis(pentyloxy) triphenylene (H5T) and 2-(acryloyloxypropyloxy)-3,6,7,10,11-pentapentylox-triphenylene (TPh-3A), with an electron acceptor, β-(2,4,7-trinitro-9-fluorenylideneaminooxy) propionic acid (TNF-carb). The structure of thin supported films of H5T, TPh-3A and their blends with TNF-carb was investigated by grazing-incidence wide-angle X-ray scattering using a synchrotron source. At room temperature, the pristine discotics crystallize in orthorhombic unit cells whereas the self-assembly of H5T and TPh-3A with TNF-carb results in a double gyroid and hexagonal phases, respectively. Formation of the double gyroid phase with the lattice parameter of 36.5 ? is driven by phase separation between the aromatic and alkyl regions of the system. It is supposed that the TNF-carb molecules of the complex are positioned in the nodes of the structure while the H5T molecules are located in the struts adjoining the nodes via triple junctions. For the hexagonal crystal of the TPh-3A/TNF-carb complex, the acceptor molecules are likely located in the interstices between the neighboring supramolecular columns of TPh-3A. The molecular structures of the blends were also explored by means of FTIR spectroscopy. A detailed FTIR spectra analysis illustrates fine changes in inter-molecular bonds. For example, the initially dimerized acceptor molecules totally disappear in the complex structures whereas in TPh-3A/TNF-carb additional H-bonds between the carboxylate group in TNF-carb and the ester group of TPh-3A form. The experimental data allows putting forward possible molecular models of the complex structures. This journal is
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
supporting information, 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.
The leading role of the steric hindrance effect and dipole-dipole interaction in superlattice nanostructures formed via the assembly of discotic liquid crystals
Zhang, Zhenhu,Yang, Huanzhi,Bi, Jingze,Zhang, Ao,Fang, Yi,Feng, Yuwen,An, Li,Liang, Lijuan,Zhang, Chunxiu,Pu, Jialing
supporting information, p. 20087 - 20094 (2018/12/13)
To reveal the relationships among molecular structures, self-assembly behavior and the organic electronic properties of discotic liquid crystals, 2-(neopentyloxy)-3,6,7,10,11-pentakis(pentyloxy)triphenylene (T5ON1) and 2-pivalate-3,6,7,10,11-penta-pentylo
