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

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 dialky...

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Bibliographic Details
Published in:Dalton transactions : an international journal of inorganic chemistry 2012-10, Vol.41 (38), p.11651-11656
Main Authors: Vachova, Lenka, Novakova, Veronika, Kopecky, Kamil, Miletin, Miroslav, Zimcik, Petr
Format: Article
Language:English
Subjects:
Coordination Complexes - chemistry
Indoles - chemistry
Magnesium - chemistry
Quantum Theory
Singlet Oxygen - chemistry
Singlet Oxygen - metabolism
Spectrometry, Fluorescence
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Summary: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.
ISSN:1477-9226
1477-9234
DOI:10.1039/c2dt31403g