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Organic thin film transistors (OTFTs); oligothiophenes; electron-deficient core; electro-optical properties; charge transfer.

In order to tune the optoelectronic and charge transfer properties of 4,6-di(thiophen-2-yl)pyrimidine (1), some new compounds were designed, i.e., 4,6-bis(benzo[$b$]thiophen-2-yl)pyrimidine (2), 4,6-bis(naphtho[2,3-b]thiophen-2-yl)pyrimidine (3), 4,6-bis(anthra[2,3-b]thiophen-2-yl)pyrimidine (4), 4,6-bis(tetraceno[2,3-$b$]thiophen-2-yl)pyrimidine (5) and 4,6-bis(pentaceno[2,3-$b$]thiophen-2-yl)pyrimidine (6). Compounds 2–6 were designed by assimilation of benzene, naphthalene, anthracene, tetracene and pentacene, respectively at both ends of compound 1. Integration of oligocene end cores reduces the energy gap resulting in a red shift in the absorption and fluorescence emission spectra. The legible intra-molecularcharge transfer is significant from electron-rich moieties to the electron-deficient core (pyrimidine). The elongation of $\pi$-conjugation led to escalate the electron affinity, lower the ionization potential and hole reorganization energy. The hole reorganization energies of compounds 3–6 exposed that these materials would be effective hole transport contenders to be used in diverse semiconductor devices.

AHMAD IRFAN¹ ABDULLAH G AL-SEHEMI¹ MOHAMMED A ASSIRI¹ MUHAMMAD WASEEM MUMTAZ²

1. Department of Chemistry, Faculty of Science, King Khalid University, P.O. Box 9004, Abha 61413, Saudi Arabia
2. Department of Chemistry, University of Gujrat, Gujrat, Punjab 50700, Pakistan

Published

15 August 2019

Manuscript received

9 October 2018

Accepted

20 December 2018