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.
Bibliographical noteFunding 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.
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All Science Journal Classification (ASJC) codes
- Organic Chemistry