Synthesis, Crystal Structure and Quantum-chemical Calculation of Novel π-Extended Tetrathiafulvalene Derivatives

doi:10.7503/cjcu20120694

Abstract

Abstract:

Two novel π-extended tetrathiafulvalene derivatives, N,N'-bisbenzene-1,4-diamine(5a) and N,N'-bisbenzene-\{1,4-diamine(5b) were synthesized with p-phenylenediamine as starting material. The molecular structures were identified and characterized by ¹H NMR, mass spectrometry(MS), Fourier transform infrared(FTIR) and single-crystal X-ray diffraction(XRD). Crystal structure analysis shows that compounds 5a and 5b belong to triclinic and monoclinic system, with space group P1 and P2₁/n, respectively. The planes of the bis(imino)benzene in compounds 5a and 5b twisted from the plane of the two dithiole rings with a dihedral angle of 87.61° for compound 5a, and 43.77° for compound 5b, respectively. Moreover, the density functional theory(DFT) calculations are also carried out with Gaussian 09 program at the B3LYP/6-31+G(d,p) level to investigate the frontier orbital, electrostatic potential and spectroscopy. The experimental results are generally in good agreement with those obtained from DFT calculations.

Key words: Tetrathiafulvalene, Crystal structure, Density functional theory

CLC Number:

O621
O641

TrendMD:

ZHU Yu-Lan, CAO Li, MA Kui-Rong, TIAN Li-Bin, WANG Xin-Long, SU Zhong-Min. Synthesis, Crystal Structure and Quantum-chemical Calculation of Novel π-Extended Tetrathiafulvalene Derivatives[J]. Chem. J. Chinese Universities, 2013, 34(4): 952.

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