Theoretical study on the charge transport properties of triphenylene discogens with a phenylpropionyloxy or 3-phenylpropenoyloxy side chain

Abstract

Charge transport is one of the most important properties in organic materials. Charge transport properties of triphenylene discogens with a phenylpropionyloxy or 3-phenylpropenoyloxy side chain have been investigated computationally on the basis of semi-classical Marcus theory. The results show that three triphenylene derivatives have high charge mobility. Title compounds have much better electronic mobility than the triphenylene. The triphenylenes containing 3-phenylpropenoyloxy have better hole mobility, but smaller electronic mobility than the triphenylenes with phenylpropionyloxy. For the triphenylene discogens with a phenylpropionyloxy, the longer the alkloxy chains, the better the positive charge transfer rate, but the smaller the negative charge transfer rate.triphenylene, charge transport, discotic liquid crystals, phenylpropilate, phenylpropenoate

Theoretical Approach to the Study of Thiophene-Based Discotic Systems As Organic Semiconductors

“…According to the M06-2X (B3LYP) method, the relative energy profile shows a minimum located at 40° (45°) for D 3 h symmetry compounds (RO-TriPh and RO-TriT) and at 30° (35°) and 60° (65°) for RO-BiPhT and RO-TetraT, respectively. Liquid crystal triphenylene derivatives show an experimental azimuthal angle of ∼45°. ,,,− For all molecules studied, azimuthal angles obtained from cluster optimization lie between those calculated from M06-2X and B3LYP using a restricted energy profile. The difference in the azimuthal angles attained after cluster optimization or using a restricted energy profile for a dimer model could be due, in part, to the different environment in each case.…”

“…The combined weak nature of the intermolecular interactions and the sensitivity of the transfer integrals to nuclear displacements make charge mobility parameters sensitive to the local ordering and relative disposition between molecules. , In general, charge transport is favored by face-to-face configurations even though they do not match the most favorable interdisc interaction potential energy. Therefore, it is important to get reliable intermolecular potential energy curves.…”

“…In the case of π-conjugated oligomers and polymers, thiophene based-materials have proven to be a good choice for an assortment of applications (see for instance ref ). However in the case of discotic systems, most of the works deal only with carbon-based molecules, such as triphenylene (TriPh, Figure a) related discotic systems (see refs − and − and references therein). Thus, very few works on thiophene-based discotic systems and their applications as organic semiconductors are known (see for instance refs and ).…”

“…Although we are only interested in the charge transport related properties for the selected aromatic cores, a deeper study would require side chains to be also considered since they could affect π-interactions between different discs and, therefore, charge transport. 3,4,14,17 2. THEORETICAL METHODOLOGY All of the calculations were performed with Gaussian 09 (revision A.02).…”

Theoretical investigations on charge transport properties of tetrabenzo[a,d,j,m]coronene derivatives using different density functional theory functionals (B3LYP, M06-2X, and wB97XD)

“…At present, highly reliable and computationally cheap quantum chemical methods, such as density functional theory (DFT), are being widely used in the field of organic optoelectronics to validate the results of experimental studies and to predict the performance of novel organic semiconductor molecules. Based on DFT quantum chemistry, researchers have calculated and predicted the intrinsic electron and hole transport rates of organic molecular systems with various molecular structures, substituents, or hybridizations, including molecular derivatives such as thiophene, 2 bithiazole, 3 tetracene, 4 anthracene, 5,6 pentacene, [7][8][9] heptacenes, 10 diindole-diimide, 11 perylene, 12,13 triphenylene, 14,15 truxene, 16,17 coronene, 18 and phthalocyanine. 19,20 These theoretical studies on the relationship between the molecular structures of different systems and their charge transport properties are extremely useful for guiding experimental studies.…”