NDLI: The effect of “on/off” molecular switching on the photophysical and photochemical properties of axially calixarene substituted activatable silicon(IV)phthalocyanine photosensitizers

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Altinbas Özpinar, Gül Ahsen, Vefa Durmus, Mahmut Güngör, Ömer
Description	Author Affiliation: Güngör Ö ( Department of Chemistry, Gebze Technical University, P.O. Box: 141, Gebze, 41400, Kocaeli, Turkey. durmus@gtu.edu.tr and Department of Chemistry Technology, Kocaeli University, Advance Vocational School of Hereke Omer Ismet Uzunyol, Kocaeli, 41800, Turkey.); Altinbas Özpinar G ( Department of Chemistry Engineering, Çanakkale Onsekiz Mart University, Faculty of Engineering, Terzioglu Campus, 17100, Çanakkale, Turkey.); Durmus M ( Department of Chemistry, Gebze Technical University, P.O. Box: 141, Gebze, 41400, Kocaeli, Turkey. durmus@gtu.edu.tr.); Ahsen V ( Department of Chemistry, Gebze Technical University, P.O. Box: 141, Gebze, 41400, Kocaeli, Turkey. durmus@gtu.edu.tr.)
Abstract	Silicon(IV) phthalocyanines (4 and 5) bearing two calixarene groups as axial ligands were synthesized. Surprisingly, both phthalocyanines were obtained as two different isomers (4a–b and 5a–b) depending on the distance between calixarene benzene groups and the phthalocyanine ring. DFT and TD-DFT computations were performed to model plausible structures of these isomers and to simulate electronic absorption spectra. These isomers converted into each other depending on the polarity of the used solvent, temperature and light irradiation. The photophysical and photochemical properties of each isomer were investigated in dimethylsulfoxide (DMSO) for the determination of photodynamic therapy (PDT) activities of these compounds. The more blue-shifted isomers (4b and 5b) showed higher fluorescence quantum yields and singlet oxygen generation compared to more red-shifted counterparts (4a and 5a). This behavior is extremely important for developing activatable photosensitizers for cancer treatment by PDT. Although these photosensitizers produce lower singlet oxygen in normal cells, they produce higher singlet oxygen (six times higher for 5b) in cancer cells since these photosensitizers converted to more blue-shifted isomers by using light irradiation.
ISSN	14779226
Issue Number	18
Journal	Dalton Trans.
Volume Number	45
e-ISSN	13645447
Language	English
Publisher	Royal Society of Chemistry
Publisher Date	2016-05-04
Publisher Place	Great Britain (UK)
Access Restriction	Subscribed
Subject Keyword	Chemistry
Content Type	Text
Resource Type	Article
Subject	Inorganic Chemistry

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