Synthesis and properties of fully conjugated macrocycles composed of m-diethynylene-phenylene-bridged two dibenzofuran,dibenzothiophene and carbazole units |
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| Authors: | Toshiaki Shimasaki Shunsuke Okajima Rino Ishikawa Shinji Kawaguchi Takeshi Akimoto Naoto Asano Tetsuo Iwanaga Motonori Watanabe Naozumi Teramoto Mitsuhiro Shibata |
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| Affiliation: | 1. Department of Applied Chemistry, Faculty of Engineering, Chiba Institute of Technology, Narashino, Chiba, 275-0016, Japan;2. Department of Chemistry, Faculty of Science, Okayama University of Science, 1-1 Ridaicho, Kita-ku, Okayama, 700-0005, Japan;3. International Institute for Carbon-Neutral Energy Research (I2CNER), Molecular Photoconversion Devices Division, Kyushu University, 744 Motooka, Nishi-ku, Fukuoka, 819-0395, Japan |
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| Abstract: | Fully conjugated macrocycles 1a?1c composed of m-diethynylene-phenylene-bridged two dibenzofuran, dibenzothiophene and carbazole units were synthesized via Sonogashira cross coupling reactions under high-diluted condition. These conjugated macrocycles were fully characterized by 1H NMR, 13C NMR, FT-IR, Mass spectroscopies and elemental analysis. Photophysical and redox properties of 1a?1c were investigated by means of UV–vis/fluorescence spectroscopies and cyclic voltammetry, respectively, and those features were compared with those of the corresponding linear phenylethynyldibenzoheterols 11a?11c. Furthermore, their structural and electronic insights were studied by theoretical calculations at the B3LYP/cc-pVDZ//B3LYP/6-31G(d) level of theory. |
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| Keywords: | Conjugated macrocycle Dibenzoheteroles UV–vis spectra Fluorescence Cyclic voltammetry DFT calculation |
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