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Effect of Axial Ligands on the Molecular Configurations, Stability, Reactivity, and Photodynamic Activities of Silicon Phthalocyanines
Author(s) -
Luan Liqiang,
Ding Lanlan,
Shi Jiawei,
Fang Wenjuan,
Ni Yuxing,
Liu Wei
Publication year - 2014
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201402813
Subject(s) - singlet oxygen , photodynamic therapy , phthalocyanine , reactivity (psychology) , chemistry , ligand (biochemistry) , photochemistry , quantum yield , porphyrin , yield (engineering) , ring (chemistry) , singlet state , silicon , crystallography , oxygen , materials science , fluorescence , organic chemistry , receptor , excited state , medicine , biochemistry , physics , alternative medicine , pathology , nuclear physics , metallurgy , quantum mechanics
To demonstrate the effect of axial ligands on the structure–activity relationship, a series of axially substituted silicon phthalocyanines (SiPcs) have been synthesized with changes to the axial ligands. The reactivity of the axial ligand upon shielding by the phthalocyanine ring current, along with their stability, photophysical, and photodynamic therapy (PDT) activities were compared and evaluated for the first time. As revealed by single‐crystal XRD analysis, rotation of the axial OMe ligands was observed in SiPc 3 , which resulted in two molecular configurations coexisting synchronously in both the solid and solution states and causing a split of the phthalocyanine α protons in the 1 H NMR spectra that is significantly different from all SiPcs reported so far. The remarkable photostability, good singlet oxygen quantum yield, and efficient in vitro photodynamic activity synergistically show that compound 3 is one of the most promising photosensitizers for PDT.