Synthesis and Characterization of Novel Pyrene Derivatives Containing Thienyl Groups

Duan, Zongfan; Hoshino, Daiki; Yang, Zhigang; Yano, Hiroaki; Ueki, Hideharu; Liu, Yingwei; Ohuchi, Hirokuni; Takayanagi, Yutaro; Zhao, Gaoyang; Nishioka, Yasushiro

doi:10.1080/15421406.2011.564018

Cited by 2 publications

(2 citation statements)

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“…Scheme 1 outlines the synthetic pathways to prepare THTP, TTP, and THTP-C. The facile synthetic approach for pyrene derivatives THTP and TTP with pendant thienyl rings mainly involved Friedel-Crafts alkylation, bromination, and Stille coupling reactions and was performed [ 11 ].…”

Section: Resultsmentioning

confidence: 99%

“…Pyrene and its derivatives are well known as polycyclic aromatic hydrocarbons, and are mainly used as electro-conductive and photo-sensitive materials [ 8 , 9 , 10 ]. We have reported the successful synthesis of two new thiophene-containing oligomers based on a pyrene core with pendant thienyl rings [ 11 ]; an expanded and elongated conjugated system would be expected to lead to even more interesting electronic and optical properties. In this paper, FeCl 3 -mediated oxidative cyclization of 4,5,9,10-tetra[2-(5-hexyl)thienyl]-2,7-di- tert -butylpyrene (THTP) was used to construct an extended thiophene-pendant pyrene skeleton via thienyl-thienyl carbon-carbon bond formation and to eventually obtain the flat molecule THTP-C with a larger rigid tetracene core ( Scheme 1 ).…”

Section: Introductionmentioning

confidence: 99%

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

et al. 2011

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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.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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

et al. 2011

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Regioselective (thio)carbamoylation of 2,7-di-tert-butylpyrene at the 1-position with iso(thio)cyanates

Wrona-Piotrowicz¹,

Witalewska²,

Zakrzewski³

et al. 2017

Beilstein J. Org. Chem.

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It has been found that 2,7-di-tert-butylpyrene reacts with aliphatic iso(thio)cyanates in the presence of trifluoromethanesulfonic acid to exclusively afford the corresponding 1-substituted (thio)amides in high yields. For aromatic iso(thio)cyanates the reaction is less regioselective, although substitution at the 1-position prevails. For ethoxycarbonyl isothiocyanate, apart from the 1-substituted thioamide, 1,8-disubstituted thioamide and 2,7-di-tert-butylpyrene-1-carbonitrile are formed (especially at longer reaction times).

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Synthesis and Characterization of Novel Pyrene Derivatives Containing Thienyl Groups

Cited by 2 publications

References 26 publications

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

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

Regioselective (thio)carbamoylation of 2,7-di-tert-butylpyrene at the 1-position with iso(thio)cyanates

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