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

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

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 (CC BY 3.0).

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MDPI and ACS Style

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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