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Extremely Photostable Electron‐Deficient Phthalocyanines that Generate High Levels of Singlet Oxygen
Author(s) -
Furuyama Taniyuki,
Miyaji Yusuke,
Maeda Kazuya,
Maeda Hajime,
Segi Masahito
Publication year - 2019
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.201805082
Subject(s) - singlet oxygen , phthalocyanine , photochemistry , polar effect , chemistry , oxygen , singlet state , metal , palladium , catalysis , organic chemistry , excited state , physics , nuclear physics
A robust lead‐mediated synthetic procedure for the generation of phthalocyanines substituted with electron‐withdrawing groups has been developed. The free‐base phthalocyanine and various metal complexes were prepared without discernible degradation of the peripheral electron‐withdrawing substituents. Upon irradiation with red light, some of the thus‐obtained metal complexes generated high levels of singlet oxygen. In particular, a palladium complex exhibited attractive photostability upon exposure to singlet oxygen as a bleaching agent. The photostability of such complexes that may manifest concomitantly to the generation of high levels of singlet oxygen was attributed to the presence of the electron‐withdrawing groups, which results in energetically low‐lying highest occupied molecular orbitals.