ortho-Phenylene-Bridged Hybrid Nanorings of 2,5-Pyrrolylenes and 2,5-Thienylenes

Fengkun Chen, Jinseok Kim, Yusuke Matsuo, Yongseok Hong, Dongho Kim, Takayuki Tanaka, Atsuhiro Osuka

Research output: Contribution to journalArticlepeer-review

8 Citations (Scopus)

Abstract

Hybrid nanorings composed of 2,5-pyrrolylene, 2,5-thienylene, and bridging ortho-phenylene were synthesized by strategic cross-coupling reactions, and their structures were unambiguously revealed by X-ray diffraction analysis. These nanorings showed highly twisted structures in the solid-state, while exhibiting symmetric 1H NMR spectra, indicating their conformational flexibilities in solution. The photophysical and electrochemical properties of these nanorings were studied in detail by UV/Vis and fluorescence spectroscopy, femto-second laser-based spectroscopy, and cyclic voltammetry with the aid of DFT calculations. It is shown that hybridization of nanorings with 2,5-thienylene and 2,5-pyrrolylene is an effective means to tune their electronic properties.

Original languageEnglish
Pages (from-to)994-1000
Number of pages7
JournalAsian Journal of Organic Chemistry
Volume8
Issue number7
DOIs
Publication statusPublished - 2019 Jul

Bibliographical note

Funding Information:
This work was supported by JSPS KAKENHI Grant Numbers (JP26810021, JP18H03910, and JP18K14199). The work at Yonsei University was supported by Global Research Laboratory (2013K1A1A2A02050183) through the National Research Foundation of Korea.

Publisher Copyright:
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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