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

FeCl(3)-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 (1)H-NMR, (13)C-NMR, MS, and elemental anal...

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Autores principales: Duan, Zong-Fan, Huang, Xian-Qiang, Yang, Zhi-Gang, Hoshino, Daiki, Kitanaka, Susumu, Zhao, Gao-Yang, Nishioka, Yasushiro
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2011
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6264305/
https://www.ncbi.nlm.nih.gov/pubmed/21623316
http://dx.doi.org/10.3390/molecules16064467
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author Duan, Zong-Fan
Huang, Xian-Qiang
Yang, Zhi-Gang
Hoshino, Daiki
Kitanaka, Susumu
Zhao, Gao-Yang
Nishioka, Yasushiro
author_facet Duan, Zong-Fan
Huang, Xian-Qiang
Yang, Zhi-Gang
Hoshino, Daiki
Kitanaka, Susumu
Zhao, Gao-Yang
Nishioka, Yasushiro
author_sort Duan, Zong-Fan
collection PubMed
description FeCl(3)-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 (1)H-NMR, (13)C-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 (1)H-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.
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spelling pubmed-62643052018-12-10 A Novel Thiophene-Fused Polycyclic Aromatic with a Tetracene Core: Synthesis, Characterization, Optical and Electrochemical Properties Duan, Zong-Fan Huang, Xian-Qiang Yang, Zhi-Gang Hoshino, Daiki Kitanaka, Susumu Zhao, Gao-Yang Nishioka, Yasushiro Molecules Article FeCl(3)-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 (1)H-NMR, (13)C-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 (1)H-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. MDPI 2011-05-27 /pmc/articles/PMC6264305/ /pubmed/21623316 http://dx.doi.org/10.3390/molecules16064467 Text en © 2011 by the authors; licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Duan, Zong-Fan
Huang, Xian-Qiang
Yang, Zhi-Gang
Hoshino, Daiki
Kitanaka, Susumu
Zhao, Gao-Yang
Nishioka, Yasushiro
A Novel Thiophene-Fused Polycyclic Aromatic with a Tetracene Core: Synthesis, Characterization, Optical and Electrochemical Properties
title A Novel Thiophene-Fused Polycyclic Aromatic with a Tetracene Core: Synthesis, Characterization, Optical and Electrochemical Properties
title_full A Novel Thiophene-Fused Polycyclic Aromatic with a Tetracene Core: Synthesis, Characterization, Optical and Electrochemical Properties
title_fullStr A Novel Thiophene-Fused Polycyclic Aromatic with a Tetracene Core: Synthesis, Characterization, Optical and Electrochemical Properties
title_full_unstemmed A Novel Thiophene-Fused Polycyclic Aromatic with a Tetracene Core: Synthesis, Characterization, Optical and Electrochemical Properties
title_short A Novel Thiophene-Fused Polycyclic Aromatic with a Tetracene Core: Synthesis, Characterization, Optical and Electrochemical Properties
title_sort novel thiophene-fused polycyclic aromatic with a tetracene core: synthesis, characterization, optical and electrochemical properties
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6264305/
https://www.ncbi.nlm.nih.gov/pubmed/21623316
http://dx.doi.org/10.3390/molecules16064467
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