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Molecules 2011, 16(6), 4467-4481; doi:10.3390/molecules16064467
Article

A Novel Thiophene-Fused Polycyclic Aromatic with a Tetracene Core: Synthesis, Characterization, Optical and Electrochemical Properties

1,2,* , 3, 4, 1, 4, 2 and 1,*
1 College of Science and Technology, Nihon University, Narashinodai, Funabashi, Chiba 2748501, Japan 2 School of Materials Science and Engineering, Xi’an University of Technology, Xi’an 710048, China 3 College of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, China 4 College of Pharmacy, Nihon University, Narashinodai, Funabashi, Chiba 2748555, Japan
* Authors to whom correspondence should be addressed.
Received: 9 May 2011 / Revised: 25 May 2011 / Accepted: 25 May 2011 / Published: 27 May 2011
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Abstract

FeCl3-mediated oxidative cyclization was successfully used to construct an extended thiophene-pendant pyrene skeleton and synthesize a novel thiophene-fused polycyclic aromatic (THTP-C) with a tetracene core. The identity of the compound was confirmed by 1H-NMR, 13C-NMR, MS, and elemental analysis. Meanwhile, a single crystal of THTP-C was obtained and analyzed by X-ray single-crystal diffraction. THTP-C has a “saddle” shaped π-conjugated 1-D supramolecular structure, and favors highly ordered self-assembly by π-π interactions as evidenced by its concentration-dependent 1H-NMR spectra in solution. The optical properties of THTP-C were investigated by ultraviolet-visible (UV-Vis) and photoluminescence (PL) spectroscopy and its electrochemical properties were investigated by cyclic voltammetry (CV). The relatively large band gap (2.86 eV), low EHOMO level (−5.64 eV) and intermolecular π-π interactions imply that THTP-C has a high stability against photo-degradation and oxidation, and may be a promising candidate for stable hole-transporting materials.
Keywords: polycyclic aromatics; oxidative cyclization; organic semiconductor materials polycyclic aromatics; oxidative cyclization; organic semiconductor materials
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Duan, Z.-F.; Huang, X.-Q.; Yang, Z.-G.; Hoshino, D.; Kitanaka, S.; Zhao, G.-Y.; Nishioka, Y. A Novel Thiophene-Fused Polycyclic Aromatic with a Tetracene Core: Synthesis, Characterization, Optical and Electrochemical Properties. Molecules 2011, 16, 4467-4481.

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