Ortho‐Phenylene‐Bridged Hybrid Nanorings of 2, 5‐Pyrrolylenes and 2, 5‐Thienylenes. Issue 7 (18th April 2019)

• Record Type: Journal Article
• Authors: Chen, Fengkun; Kim, Jinseok; Matsuo, Yusuke; Hong, Yongseok; Kim, Dongho; Tanaka, Takayuki; Osuka, Atsuhiro
• Is Part Of: Asian journal of organic chemistry. Volume 8:Issue 7(2019)
• Page Start: 994
• Page End: 1000
• Publication Date: 2019-04-18
• Subjects: heterocycles -- hybrid nanorings -- cross-coupling -- absorption -- emission; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.201900168
• Languages: English
• ISSNs: 2193-5807

Abstract

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 1 H 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. Abstract : Twisted rings : Conjugated nanorings composed of 2, 5‐pyrrolylene and 2, 5‐thienylene bridged by ortho ‐phenylenes were synthesized. The solid‐state structures proved to be highly twisted, depending on the ratio of thienylene and pyrrolylene units. The optical and electrochemical properties were also studied, demonstrating the tunability of these properties by hybridization.