Synthesis of mono-, di-, tri- and tetracarboxy azaphthalocyanines as potential dark quenchers

Autor:	Veronika Novakova, Kamil Kopecky, Antonín Svoboda, Miroslav Miletin, Petr Zimcik, Dalibor Šatínský
Rok vydání:	2011
Předmět:	Hexanoic acid Singlet oxygen Process Chemistry and Technology General Chemical Engineering Medicinal chemistry High-performance liquid chromatography chemistry.chemical_compound chemistry Phthalocyanine Organic chemistry Reactivity (chemistry) Isoindole Acetonitrile Tetrahydrofuran
Zdroj:	Dyes and Pigments. 91:112-119
ISSN:	0143-7208
DOI:	10.1016/j.dyepig.2011.03.016
Popis:	Mono-, di-, tri- and tetracarboxy-substituted metal-free azaphthalocyanines (AzaPc) were synthesized from 5,6-bis(diethylamino)pyrazine-2,3-dicarbonitrile and 6-(5,6-dicyano-3-(diethylamino)pyrazin-2-ylamino)hexanoic acid using a statistical condensation approach. AzaPc bearing eight diethylamino peripheral substituents was also isolated from the mixture. Analysis of the distribution of congeners in the statistical mixture using optimized HPLC method (Phenomenex Synergy RP Fusion column, acetonitrile/tetrahydrofuran/water (pH 5.5) 50:20:30) was performed. The analysis showed optimal ratios of starting materials to be 3:1 for AAAB, 1:3 for ABBB and 1:1 for AABB/ABAB types of the congeners. The distribution of the congeners corresponded well with calculated values indicating similar reactivity of both starting materials and no sterical constraint between adjacent isoindole units in the AzaPc ring. All investigated AzaPc showed no fluorescence, extremely low singlet oxygen quantum yields ( Φ ∆
Databáze:	OpenAIRE
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