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Novel axially-substituted silicon phthalocyanines with pH-modulated fluorescence ON/OFF switching properties

Belgin Şahin

Gebze Technical University, Faculty of Science, Department of Chemistry, 41400, Gebze, Kocaeli, Turkey

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Merve Zeyrek Ongun

Dokuz Eylul University, Chemistry Technology Program, Izmir Vocational High School, 35160, Izmir, Turkey

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Sevinc Zehra Topal

Gebze Technical University, Faculty of Science, Department of Chemistry, 41400, Gebze, Kocaeli, Turkey

E-mail Address: sztopal@gtu.edu.tr

Corresponding author

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Ayşe Gül Gürek

Gebze Technical University, Faculty of Science, Department of Chemistry, 41400, Gebze, Kocaeli, Turkey

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, and

Devrim Atilla

Gebze Technical University, Faculty of Science, Department of Chemistry, 41400, Gebze, Kocaeli, Turkey

E-mail Address: datilla@gtu.edu.tr

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https://doi.org/10.1142/S1088424619500329Cited by:1 (Source: Crossref)

Abstract

Two novel axially-substituted asymmetric silicon (IV) phthalocyanines, the first one substituted with both polyethylene glycol and indomethacin groups (Pc1) and second one substituted with both polyethylene glycol and mefenamic acid groups (Pc2) have been designed and synthesized for the purpose of pH sensing examinations. Their absorption and fluorescence emission-based spectral properties were investigated in chloroform, tetrahydrofuran and toluene. The pH-sensing properties of Pc1 and Pc2 were examined in detail by using UV-vis absorption and fluorescence spectroscopies in tetrahydrofuran. The effects of the substituents on the spectroscopic properties and pH-sensing behavior of these silicon phthalocyanines were revealed. Pc1 didn’t show a pH response; however, Pc2 exhibited a signal increase from pH 5.40 to 0.37 (turn on) and a drastic quenching when pH went from 0.37 to 5.40 (turn off). The protonation/deprotonation stage of the NH group of Pc2 presented fluorescence-based “on-off” type molecular switch properties.

This paper is part of the 2019 Women in Porphyrin Science special issue.

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