Thiatriphyrin(2.1.1): A Core-Modified Contracted Porphyrin

Authors

  • Dr. Daiki Kuzuhara,

    1. Graduate School of Materials Science, Nara Institute of Science and Technology, Ikoma 630-0192 (Japan)
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  • Yuka Sakakibara,

    1. Graduate School of Materials Science, Nara Institute of Science and Technology, Ikoma 630-0192 (Japan)
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  • Dr. Shigeki Mori,

    1. Department of Molecular Science, Integrated Center for Sciences, Ehime University, Matsuyama 790-8577 (Japan)
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  • Prof. Dr. Tetsuo Okujima,

    1. Department of Chemistry and Biology, Graduate School of Science and Engineering, Ehime University, Matsuyama 790-8577 (Japan)
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  • Prof. Dr. Hidemitsu Uno,

    1. Department of Chemistry and Biology, Graduate School of Science and Engineering, Ehime University, Matsuyama 790-8577 (Japan)
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  • Prof. Dr. Hiroko Yamada

    Corresponding author
    1. Graduate School of Materials Science, Nara Institute of Science and Technology, Ikoma 630-0192 (Japan)
    2. CREST, JST, Chiyoda-ku, Tokyo 102-0075 (Japan)
    • Graduate School of Materials Science, Nara Institute of Science and Technology, Ikoma 630-0192 (Japan)
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  • We thank S. Katao for the measurements of X-ray diffraction and M. Yamamura and Y. Nishikawa for ESIMS measurements. This research was partly supported by Grants-in-Aid (No. 24655034 to H.Y. and D.K.) and the Green Photonics Project at NAIST sponsored by the Ministry of Education, Culture, Sports, Science and Technology, MEXT (Japan).

Abstract

original image

Elusive in its free-base form, the core-modified contracted porphyrin thiatriphyrin(2.1.1) was prepared with p-tolyl substituents by intramolecular McMurry coupling and then converted into various alkoxy-substituted analogues (see scheme; DBU=1,8-diazabicyclo[5.4.0]undec-7-ene). In the presence of trifluoroacetic acid (TFA), each of these compounds was transformed into the protonated thiatriphyrin(2.1.1), which exhibited moderate aromaticity.

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