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Introduction of Bulky Perfluoroalkyl Groups at the Periphery of Zinc Perfluorophthalocyanine: Chemical, Structural, Electronic, and Preliminary Photophysical and Biological Effects
Author(s) -
Bench Barbara A.,
Beveridge Andrew,
Sharman Wesley M.,
Diebold Gerald J.,
van Lier Johan E.,
Gorun Sergiu M.
Publication year - 2002
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/1521-3773(20020301)41:5<747::aid-anie747>3.0.co;2-j
Subject(s) - foundation (evidence) , zinc , finance , chemistry , business , political science , law , organic chemistry
A higher anticancer activity is observed in photodynamic tests with the first sterically bulky (nonplanar) perhalogenated zinc phthalocyanine (Pc), [F 64 PcZn(acetone) 2 ] (see structure: F green, N blue, O red, C gray) in comparison with planar zinc perfluorophthalocyanine. The perfluoroisopropyl substituents enhance the solubility, stabilize axial ligands (such as the coordinated acetone molecules in the structure shown), narrow the HOMO–LUMO gap, shift redox potentials, and increase the lifetime of the excited triplet state of the new complex.