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Synthesis of Helically π‐Extended N‐Confused Porphyrin Dimer via meso ‐Bipyrrole‐Bridge with Near‐Infrared‐II Absorption Capability
Author(s) -
Yamasumi Kazuhisa,
Notsuka Yusuke,
Yamaoka Yoshihisa,
Mori Shigeki,
Ishida Masatoshi,
Furuta Hiroyuki
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202002406
Subject(s) - porphyrin , metalation , pyrrole , photochemistry , dimer , chemistry , absorption (acoustics) , nickel , aromaticity , infrared , metal , crystallography , materials science , stereochemistry , organic chemistry , molecule , optics , physics , composite material
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.