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Issue 18, 2016
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The effect of “on/off” molecular switching on the photophysical and photochemical properties of axially calixarene substituted activatable silicon(iv)phthalocyanine photosensitizers

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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.

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

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Supplementary files

Article information


Submitted
04 Mar 2016
Accepted
18 Mar 2016
First published
18 Mar 2016

Dalton Trans., 2016,45, 7634-7641
Article type
Paper

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

Ö. Güngör, G. Altınbaş Özpınar, M. Durmuş and V. Ahsen, Dalton Trans., 2016, 45, 7634
DOI: 10.1039/C6DT00874G

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