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

Yusuke Mitsushige, Shigeru Yamaguchi, Byung Sun Lee, Young Mo Sung, Susanne Kuhri, Christoph A. Schierl, Dirk M. Guldi, Dongho Kim, Yutaka Matsuo

Research output: Contribution to journalArticle

35 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)16540-16543
Number of pages4
JournalJournal of the American Chemical Society
Volume134
Issue number40
DOIs
Publication statusPublished - 2012 Oct 10

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Fingerprint Dive into the research topics of 'Synthesis of thieno-bridged porphyrins: Changing the antiaromatic contribution by the direction of the thiophene ring'. Together they form a unique fingerprint.

  • Cite this

    Mitsushige, Y., Yamaguchi, S., Lee, B. S., Sung, Y. M., Kuhri, S., Schierl, C. A., Guldi, D. M., Kim, D., & 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