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

34 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

Fingerprint

Thiophenes
Porphyrins
Thiophene
Time and motion study
Near-Infrared Spectroscopy
X ray crystallography
X Ray Crystallography
Anisotropy
Induced currents
Chemical shift
Absorption spectroscopy
Photons
Excited states
Nuclear magnetic resonance spectroscopy
Direction compound
Current density
Magnetic Resonance Spectroscopy
Electrons
Networks (circuits)

All Science Journal Classification (ASJC) codes

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

Cite this

Mitsushige, Y., Yamaguchi, S., Lee, B. S., Sung, Y. M., Kuhri, S., Schierl, C. A., ... 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
Mitsushige, Yusuke ; Yamaguchi, Shigeru ; Lee, Byung Sun ; Sung, Young Mo ; Kuhri, Susanne ; Schierl, Christoph A. ; Guldi, Dirk M. ; Kim, Dongho ; Matsuo, Yutaka. / Synthesis of thieno-bridged porphyrins : Changing the antiaromatic contribution by the direction of the thiophene ring. In: Journal of the American Chemical Society. 2012 ; Vol. 134, No. 40. pp. 16540-16543.
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Mitsushige, Y, Yamaguchi, S, Lee, BS, Sung, YM, Kuhri, S, Schierl, CA, Guldi, DM, 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, vol. 134, no. 40, pp. 16540-16543. https://doi.org/10.1021/ja3082999

Synthesis of thieno-bridged porphyrins : Changing the antiaromatic contribution by the direction of the thiophene ring. / Mitsushige, Yusuke; Yamaguchi, Shigeru; Lee, Byung Sun; Sung, Young Mo; Kuhri, Susanne; Schierl, Christoph A.; Guldi, Dirk M.; Kim, Dongho; Matsuo, Yutaka.

In: Journal of the American Chemical Society, Vol. 134, No. 40, 10.10.2012, p. 16540-16543.

Research output: Contribution to journalArticle

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AU - Mitsushige, Yusuke

AU - Yamaguchi, Shigeru

AU - Lee, Byung Sun

AU - Sung, Young Mo

AU - Kuhri, Susanne

AU - Schierl, Christoph A.

AU - Guldi, Dirk M.

AU - Kim, Dongho

AU - Matsuo, Yutaka

PY - 2012/10/10

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N2 - 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.

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