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Synthesis, Structures, and Near‐IR Absorption of Heterole‐Fused Earring Porphyrins
Author(s) -
Wu Licheng,
Li Feilong,
Rao Yutao,
Wen Bin,
Xu Ling,
Zhou Mingbo,
Tanaka Takayuki,
Osuka Atsuhiro,
Song Jianxin
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201903446
Subject(s) - pyrrole , porphyrin , thiophene , regioselectivity , chemistry , absorption (acoustics) , oxidative coupling of methane , ring (chemistry) , coupling reaction , photochemistry , polymer chemistry , organic chemistry , materials science , catalysis , composite material
A reaction sequence of regioselective peripheral bromination, Suzuki–Miyaura coupling with 2‐borylated thiophene or pyrrole, and oxidative ring‐closure with FeCl 3 allowed the synthesis of heterole‐fused earring porphyrins 4Pd and 9Pd from the parent earring porphyrin 1 . Differently pyrrole‐fused porphyrins 5H and 6H and their Pd II complexes 5Pd and 6Pd were also synthesized. The structures of 4Pd , 5H, 6Pd , and 8Pd have been revealed by X‐ray analysis to be slightly twisted owing to constraints imposed by heterole‐fused structures. 5Pd exhibits an intensified band at 1505 nm, while 4Pd and 9Pd display small but remarkably red‐shifted absorption bands reaching around 2200 nm.