期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 134, 期 40, 页码 16540-16543出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja3082999
关键词
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资金
- Funding Program for Next-Generation World-Leading Researchers
- Midcareer Researcher Program [2010-0029668]
- Ministry of Education, Science, and Technology (MEST) of Korea [R32-2010-000-10217]
- Deutsche Forschungsgemeinschaft Cluster of Excellence
- NDRL
- Division of Chemical Sciences, Geosciences and Biosciences, Basic Energy Sciences, Office of Science, United States Department of Energy [DE-FC02-04ER15533]
Two types of thieno-bridged porphyrins were synthesized by incorporating a thiophene group across their meso and beta positions with different directions of the thiophene ring to investigate the aromaticity of these porphyrins with extended pi-systems. The 2,3-thienobridged porphyrin showed a larger antiaromatic contribution than did the 3,4-thieno-bridged porphyrin. In the former, the antiaromatic contribution is based on a 20-pi-electron conjugated circuit. The two thieno-bridged porphyrins were characterized by calculations of nucleus-independent chemical shift and anisotropy of the induced current density as well as by X-ray crystallography, NMR spectroscopy, UV-vis-NIR absorption spectroscopy, electrochemical studies, time-resolved excited-state analysis, and two-photon absorption cross section measurements. Chemical derivatization of the 2,3-thieno-bridged porphyrin was also demonstrated.
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