Synthesis of Helically π-Extended N-Confused Porphyrin Dimer via meso-Bipyrrole-Bridge with Near-Infrared-II Absorption Capability

Kazuhisa Yamasumi, Yusuke Notsuka, Yoshihisa Yamaoka, Shigeki Mori, Masatoshi Ishida, Hiroyuki Furuta

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)

Abstract

Quinoidal dimeric porphyrin dye synthesis exhibiting second near-infrared (NIR-II) absorbability is described herein. A precisely designed meso-pyrrolyl-substituted N-confused porphyrin possesses a distinct metal coordination site at the periphery. Nickel metalation of this compound led to the oxidative C−H coupling between adjacent α-pyrrole rings, affording two dimeric complexes, which exhibited intense NIR-II absorptions ranging from 1000 to 1400 nm. As was evidenced by decreased aromaticity, the quinoidal resonant structures contributed to the emergence of photoacoustic spectral capabilities in the NIR-II window. Thus, the potential of these compounds as prototypical contrast agents in various bioimaging applications has been demonstrated.

Original languageEnglish
Pages (from-to)13590-13594
Number of pages5
JournalChemistry - A European Journal
Volume26
Issue number60
DOIs
Publication statusPublished - Oct 27 2020

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

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