Subphthalocyanine basicity: reversible protonation at the azomethine bridge

Abstract : Subphthalocyanine (SubPc) could be reversibly protonated at the azomethine bridge. This phenomenon was examined by addressing the pKa of the acid (TFA, MSA, TMSA) and the SubPc electron-withdrawing properties of the peripheral isoindolic substituents (F12 vs. H12 and NO2), which tunes the basic character of the azomethine moiety. The protonation of up to three azomethines was suggested and monitored spectrophotometrically with the appearance of new absorption bands at 610, 630 nm and 660 nm, together with marked colour changes from purple to blue to green. Evidence of such a protonation was also shown by significant changes in the 1H-NMR spectrum and new bands in the infrared spectrum.
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https://hal-univ-bourgogne.archives-ouvertes.fr/hal-01660938
Contributeur : Icmub - Université de Bourgogne <>
Soumis le : lundi 11 décembre 2017 - 15:17:01
Dernière modification le : vendredi 8 juin 2018 - 14:50:12

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Yann Bernhard, Vivian Lioret, Richard A. Decréau. Subphthalocyanine basicity: reversible protonation at the azomethine bridge. New Journal of Chemistry, Royal Society of Chemistry, 2017, 〈http://pubs.rsc.org/en/Content/ArticleLanding/2018/NJ/C7NJ02957H#!divAbstract〉. 〈10.1039/C7NJ02957H〉. 〈hal-01660938〉

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