title: A novel thiophene-fused polycyclic aromatic with a tetracene core: synthesis, characterization, optical and electrochemical properties.
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 E(HOMO) 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.
authors.affiliation: College of Science and Technology, Nihon University, Narashinodai, Funabashi, Chiba 2748501, Japan. duanzf-2002@163.com
authors.forename: Zong-Fan
authors.initials: ZF
authors.lastname: Duan
authors.forename: Xian-Qiang
authors.initials: XQ
authors.lastname: Huang
authors.forename: Zhi-Gang
authors.initials: ZG
authors.lastname: Yang
authors.forename: Daiki
authors.initials: D
authors.lastname: Hoshino
authors.forename: Susumu
authors.initials: S
authors.lastname: Kitanaka
authors.forename: Gao-Yang
authors.initials: GY
authors.lastname: Zhao
authors.forename: Yasushiro
authors.initials: Y
authors.lastname: Nishioka
mesh_terms: D018360:Crystallography, X-Ray; D004563:Electrochemistry; D008958:Models, Molecular; D009279:Naphthacenes / Q000138:chemical synthesis* / Q000737:chemistry*; D019906:Nuclear Magnetic Resonance, Biomolecular; D013876:Thiophenes / Q000737:chemistry*
chemical_list: D009279:Naphthacenes; D013876:Thiophenes; C487736:naphthacene