1401686-76-7Relevant academic research and scientific papers
Synthesis of thieno-bridged porphyrins: Changing the antiaromatic contribution by the direction of the thiophene ring
Mitsushige, Yusuke,Yamaguchi, Shigeru,Matsuo, Yutaka,Lee, Byung Sun,Sung, Young Mo,Kim, Dongho,Kuhri, Susanne,Schierl, Christoph A.,Guldi, Dirk M.
supporting information, p. 16540 - 16543,4 (2020/09/15)
Two types of thieno-bridged porphyrins were synthesized by incorporating a thiophene group across their meso and β positions with different directions of the thiophene ring to investigate the aromaticity of these porphyrins with extended π-systems. The 2,3-thieno-bridged 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-π-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.
