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Issue 38, 2012
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Effect of intramolecular charge transfer on fluorescence and singlet oxygen production of phthalocyanine analogues

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Abstract

Intramolecular charge transfer (ICT) was studied on a series of magnesium, metal-free and zinc complexes of unsymmetrical tetrapyrazinoporphyrazines and tribenzopyrazinoporphyrazines bearing two dialkylamino substituents (donors) and six alkylsulfanyl or aryloxy substituents (non-donors). The dialkylamino substituents were responsible for ICT that deactivated excited states and led to considerable decrease of fluorescence and singlet oxygen quantum yields. Photophysical and photochemical properties were compared to corresponding macrocycles that do not bear any donor centers. The data showed high feasibility of ICT in the tetrapyrazinoporphyrazine macrocycle and significantly lower efficiency of this deactivation process in the tribenzopyrazinoporphyrazine type molecules. Considerable effect of non-donor peripheral substituents on ICT was also described. The results imply that tetrapyrazinoporphyrazines may be more suitable for development of new molecules investigated in applications based on ICT.

Graphical abstract: Effect of intramolecular charge transfer on fluorescence and singlet oxygen production of phthalocyanine analogues

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Publication details

The article was received on 28 Jun 2012, accepted on 12 Jul 2012 and first published on 13 Jul 2012


Article type: Paper
DOI: 10.1039/C2DT31403G
Citation: Dalton Trans., 2012,41, 11651-11656
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    Effect of intramolecular charge transfer on fluorescence and singlet oxygen production of phthalocyanine analogues

    L. Vachova, V. Novakova, K. Kopecky, M. Miletin and P. Zimcik, Dalton Trans., 2012, 41, 11651
    DOI: 10.1039/C2DT31403G

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