Theoretical Studies of Distyrylbenzene and its Optical Properties

Abstract

The electronic and geometrical properties of distyrylbenzene (DSB) are investigated by using chemistry theoretical calculation methods. Specifically, the excited state properties are studied by performing ab initio correlation interaction singlet (CIS) and time-dependent density functional theory; the ground state and Raman activities are computed by density functional theory with the B3LYP method. Eight conformers of distyrylbenzene are found and they are derived from three isomers which are cis,cis-, cis,trans-, and trans,trans-, respectively. The relative energy shows that each isomer of three types is separated with a large energy barrier, but a small energy difference of each conformer is found if they are in the same type. The transition state also shows the barrier between conformers is lower than isomers. The computed excited transition energies using ZINDO/S based on the optimized geometries at a DFT/B3LYP level with 6-31+G* show an excellent agreement with experimental absorption spectra.

Mechanistic insights into the thermal transformations of heterocyclic o-distyrylbenzenes: an experimental and computational study

“…DFT methods have previously proven to be very successful in computing structural and spectroscopic properties of the similar compounds. 21–31 For the first time, we calculated the free energy profiles for the most favorable reaction pathways for the reactions considered above, thus providing an explanation for the experimental observations concerning the thermal reaction of furyl and thienyl o -divinylbenzenes ( I–II , VII–VIII and 1–4 ) under acidic conditions. The intriguing issue of lack of reactivity of some starting precursors to obtain indane/indene products or phenantrene products, or in some cases both of them, was addressed, by (a) revealing the protonation preference of the systems under consideration, which appears to be a reaction-determining factor to produce indane/indene derivatives and (b) giving insights into the energetic requirements and formed product concerning the starting [4+2] cycloaddition step being crucial for reactions to proceed towards fenantrene products.…”

Spectroscopic and Time-Dependent DFT Study of the Photophysical Properties of Substituted 1,4-Distyrylbenzenes

“…Perhaps, the most studied OPVs are distyrylbenzene (DSBs) derivatives. The optoelectronic properties of numerous substituted DSBs have been investigated by both experimental − and computational methods. − With the goal of understanding the structure–property relationships of these technologically attractive materials, we reported the synthesis of a full trans – trans DSBs series with different electron-donating (ED) and electron-withdrawing (EW) substituents by Mizoroki–Heck cross-coupling reactions . The interest in the trans -configuration of the vinyl bonds reflects that a more-planar conformation is obtained, which facilitates conjugation and improves their optical and electronic properties. , …”