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Ayhan MM, Altınbaş Özpinar G, Durmuş M, et al. Effects of position (α or β) and linker heteroatom (O or S) of substituent on the photophysicochemical behavior of poly(oxyethylene) substituted ZnPcs and assessment of J-aggregation or protonation using TD-DFT computations. Dalton Trans. 2013;42(41):14892-904doi: 10.1039/c3dt51549d.
Ayhan, M. M., Altınbaş Özpinar, G., Durmuş, M., & Gürek, A. G. (2013). Effects of position (α or β) and linker heteroatom (O or S) of substituent on the photophysicochemical behavior of poly(oxyethylene) substituted ZnPcs and assessment of J-aggregation or protonation using TD-DFT computations. Dalton transactions (Cambridge, England : 2003), 42(41), 14892-904. https://doi.org/10.1039/c3dt51549d
Ayhan, Mehmet Menaf, et al. "Effects of position (α or β) and linker heteroatom (O or S) of substituent on the photophysicochemical behavior of poly(oxyethylene) substituted ZnPcs and assessment of J-aggregation or protonation using TD-DFT computations." Dalton transactions (Cambridge, England : 2003) vol. 42,41 (2013): 14892-904. doi: https://doi.org/10.1039/c3dt51549d
Ayhan MM, Altınbaş Özpinar G, Durmuş M, Gürek AG. Effects of position (α or β) and linker heteroatom (O or S) of substituent on the photophysicochemical behavior of poly(oxyethylene) substituted ZnPcs and assessment of J-aggregation or protonation using TD-DFT computations. Dalton Trans. 2013 Oct 01;42(41):14892-904. doi: 10.1039/c3dt51549d. PMID: 23995014.
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Dalton Trans. 2013 Oct 01;42(41):14892-904. doi: 10.1039/c3dt51549d.

Effects of position (α or β) and linker heteroatom (O or S) of substituent on the photophysicochemical behavior of poly(oxyethylene) substituted ZnPcs and assessment of J-aggregation or protonation using TD-DFT computations.

Dalton transactions (Cambridge, England : 2003)

Mehmet Menaf Ayhan, Gül Altınbaş Özpinar, Mahmut Durmuş, Ayşe Gül Gürek

Affiliations

  1. Department of Chemistry, Gebze Institute of Technology, PO Box 141, Gebze, 41400, Kocaeli, Turkey. [email protected].

PMID: 23995014 DOI: 10.1039/c3dt51549d

Abstract

A series of zinc phthalocyanines (ZnPcs) tetra-substituted with 1,3-di[2-(2-ethoxyethoxy)ethoxy]-2-propanol () or 1,3-di[2-(2-ethoxyethoxy)ethoxy]-2-propanethiol () at peripheral (β) () and non-peripheral (α) () positions have been synthesized and characterized. The spectroscopic, photophysical (fluorescence quantum yields and lifetimes) and photochemical (singlet oxygen generation and photodegradation) properties of these newly synthesized phthalocyanines have been investigated in DMSO. The effects of the position of the substituents on the phthalocyanine skeleton and the nature of the linker heteroatom on their spectroscopic, photophysical and photochemical properties have been determined. The quenching behavior of the zinc phthalocyanines by 1,4-benzoquinone has been studied in DMSO. All of the zinc(ii) Pc complexes ( and ) showed similar electronic absorption spectra in various solvents (chloroform, dichloromethane, DMF, DMSO, THF and toluene). However, complex gave an extra red-shifted band at 742 nm in chloroform and dichloromethane. DFT and TD-DFT computations were performed on the model structures (, and ) to find out the cause of the extra red-shifted Q band (J-type aggregation or protonation of the Pc ring). The computational results showed that monoprotonation of a meso nitrogen atom leads to the formation of this extra band. Photophysical and photochemical measurements indicated that these newly synthesized ZnPc derivatives are promising candidates for use as photosensitizers in the application of PDT.

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