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

12 Citations (Scopus)


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
Issue number7
Publication statusPublished - 2019 Jul

Bibliographical note

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

All Science Journal Classification (ASJC) codes

  • Organic Chemistry


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