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
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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.
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(6):4467-4481.
Duan, Zong-Fan; Huang, Xian-Qiang; Yang, Zhi-Gang; Hoshino, Daiki; Kitanaka, Susumu; Zhao, Gao-Yang; Nishioka, Yasushiro. 2011. "A Novel Thiophene-Fused Polycyclic Aromatic with a Tetracene Core: Synthesis, Characterization, Optical and Electrochemical Properties." Molecules 16, no. 6: 4467-4481.