Synthesis of thieno-bridged porphyrins: Changing the antiaromatic contribution by the direction of the thiophene ring

Mitsushige Y, Yamaguchi S, Lee BS, Sung YM, Kuhri S, Schierl C, Guldi DM, Kim D, Matsuo Y (2012)

Publication Type: Journal article, Original article

Publication year: 2012

Journal

Journal of the American Chemical Society American Chemical Society

Original Authors: Mitsushige Y., Yamaguchi S., Lee B.S., Sung Y.M., Kuhri S., Schierl C.A., Guldi D.M., Kim D., Matsuo Y.

Publisher: American Chemical Society

Book Volume: 134

Pages Range: 16540-16543

Journal Issue: 40

DOI: 10.1021/ja3082999

Abstract

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. © 2012 American Chemical Society.

Authors with CRIS profile

Susanne Kuhri Lehrstuhl für Physikalische Chemie I Christoph Schierl Lehrstuhl für Physikalische Chemie I Dirk Michael Guldi Lehrstuhl für Physikalische Chemie I

Involved external institutions

University of Tokyo JP Japan (JP) Yonsei University KR Korea, Republic of (KR)

How to cite

APA:

Mitsushige, Y., Yamaguchi, S., Lee, B.S., Sung, Y.M., Kuhri, S., Schierl, C.,... Matsuo, Y. (2012). Synthesis of thieno-bridged porphyrins: Changing the antiaromatic contribution by the direction of the thiophene ring. Journal of the American Chemical Society, 134(40), 16540-16543. https://doi.org/10.1021/ja3082999

MLA:

Mitsushige, Yusuke, et al. "Synthesis of thieno-bridged porphyrins: Changing the antiaromatic contribution by the direction of the thiophene ring." Journal of the American Chemical Society 134.40 (2012): 16540-16543.

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