Izvorni znanstveni članak

https://doi.org/10.5562/cca2787

Theoretical Investigation on Charge Transfer Properties of 1,3,5-Tripyrrolebenzene (TPB) and its Derivatives with Electron-withdrawing Substituents

Yong Hu ; Key Laboratory of Soft Chemistry and Functional Materials of MOE, School of Chemical Engineering, Nanjing University of Science and Technology, Nanjing 210094, P. R. China
Jun Yin ; Key Laboratory of Soft Chemistry and Functional Materials of MOE, School of Chemical Engineering, Nanjing University of Science and Technology, Nanjing 210094, P. R. China
Kadali Chaitanya ; Key Laboratory of Soft Chemistry and Functional Materials of MOE, School of Chemical Engineering, Nanjing University of Science and Technology, Nanjing 210094, P. R. China
Xue-Hai Ju ; Key Laboratory of Soft Chemistry and Functional Materials of MOE, School of Chemical Engineering, Nanjing University of Science and Technology, Nanjing 210094, P. R. China

Sažetak

The electronic structures and charge transport properties of 1,3,5-tripyrrolebenzene (TPB) and its substituted derivatives with
–F and –CN groups have been investigated by DFT calculations in combination with the Marcus hopping model. The dimer geometry was optimized by density functional theory method with dispersion force correction being included (DFT-D). Consequently, the charge transfer integral was evaluated. The calculation results show that the introduction of electron-withdrawing substituents does not significantly change the bond lengths and molecular symmetry of TPB, but lower the coplanarity between the pyrrole and benzene rings, especially in the case of CN substitution. Meanwhile, the introduction of electron-withdrawing groups can decrease the energy of the frontier molecular orbital and enhance the air stability. Fluorination makes the λe increase obviously while cyanation dose not. Generally speaking, the λe values of the title compounds are larger than their λh. Except for compounds 6 and 9, all others keep the face to face packing or have a slight slip in dimers, but the center of mass distances increase after fluorination or cyanation due to the distortion of the monomer’s coplanarity. The predicted quasi-one-dimensional electron mobility of the dimers is up to 0.433 cm2 V-1 s-1 at 298.15 K. The electron injection barriers of 2 and 7 are lower than that of TPB. The TPB derivatives of 1, 2, and 7 are potential n-channel materials with the high electron mobility.

This work is licensed under a Creative Commons Attribution 4.0 International License.

Ključne riječi

1,3,5-tripyrrolebenzene (TPB) and its derivatives; fluorination and cyanation; DFT; Marcus-Hush theory; organic semiconductor; charge mobility

Hrčak ID:

159414

URI

https://hrcak.srce.hr/159414

Datum izdavanja:

20.6.2016.

Posjeta: 3.017 *