Influence of push–pull configuration on the electro-optical and charge transport properties of novel naphtho-difuran derivatives: a DFT study

Abstract

We present a density functional theory (DFT) study pertaining to electro-optical and charge transport properties of two novel derivatives of diphenyl-naphtho[2,1-b:6,5-b 0 ]difuran (DPNDF) as investigated based on push-pull configuration. Both molecular structures of the designed derivatives were optimized, in ground state (S 0 ) as well as excited state (S 1 ), using DFT and time-dependent DFT (TD-DFT) respectively. The push-pull configuration effect was studied meticulously for different electro-optical properties including adiabatic/vertical electron affinity (EAa/EAv), adiabatic/vertical ionization potential (IPa/IPv) and hole/electron reorganization energies (l h /l e ), hole/electron transfer integrals (V h /V e ), hole/ electron mobility and photostability. We observed smaller l e , improved V e and higher electron mobility for compound 1 compared with the parent molecule. Our calculated value of the electron mobility for compound 1 (2.43 cm 2 V À1 s À1 ) revealed it to be an efficient electron transport material. Moreover, the influence of the push-pull on the electronic structure was also investigated by calculating the total and partial density of states (DOS). Taking advantage of the strong push-pull configurations effect on other properties, the study of the designed chemical systems was extended to their nonlinear optical (NLO) properties. Our designed novel derivatives (1 & 2) exhibited significantly larger amplitude values for first hyperpolarizability with b tot equal to 209.420 Â 10 À30 esu for compound 1 and 333.830 Â 10 À30 esu for compound 2. It was found that the first hyperpolarizability and HOMO-LUMO energy gap are in an inverse relationship for compounds 1 and 2.

In-depth quantum chemical investigation of electro-optical and charge-transport properties of trans-3-(3,4-dimethoxyphenyl)-2-(4-nitrophenyl)prop-2-enenitrile

“…It has been shown in previous studies that B3LYP is a suitable and consistent functional to calculate the properties of interest for both small and large p-conjugated organic compounds [18][19][20]. In particular, it has reproduced the experimental data for compounds such as azo dyes [21,22], triphenylamine dyes [23], chemosensors [24], phthalocyanines [25], chromene derivatives [26] and oxadiazoles [27].…”

“…Yang and co-workers reported that the direct method corresponds to ''the site-energy corrected frontier orbital splitting method'' [39]. Details can be found in the literature [13,14,19,38,41,44,45].…”

Theoretical Studies of Photophysical Properties of D−π−A−π−D-Type Diketopyrrolopyrrole-Based Molecules for Organic Light-Emitting Diodes and Organic Solar Cells

“…The PBE0/6-31G (d,p) method was applied to calculate the AIP and AEA values of the molecules. The electrostatic surface potentials can also be used to estimate the stability properties of molecules [58][59][60]. Therefore, we calculated the electrostatic surface potentials of molecules at the PBE0/6-31G (d,p) level.…”

Effect of donor strength of extended alkyl auxiliary groups on optoelectronic and charge transport properties of novel naphtha[2,1-b:6,5-b′]difuran derivatives: simple yet effective strategy

“…Previously, the photostability of organic materials was explained on the basis of MEP [37,41,67]. Recently, we pointed out that greater negative potential distributed on the system would enhance the photostability [40,41,70]. The higher negative electrostatic potential distribution on the surface will make the oxidation more difficult and resist against the degradation of the molecule (due to the oxidation and photoreactions) [37,40,41,67,70].…”

“…In our earlier study, furan ring with a very low electron reorganization energy λ (e) [36] was analyzed as a good electron transport material. Two furan rings containing DPNDF [25] has been used as parent molecule and the effects of electron withdrawing groups (EWGs) [37,38], heteroatoms substitution [39], push-pull strategy [40] and increasing conjugation [41] were investigated in our previous studies.…”