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Subphthalocyanine basicity: reversible protonation at the azomethine bridge

Abstract

Subphthalocyanine (SubPc) could be reversibly protonated at the azomethine bridge. This phenomenon was examined by adressing 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: appearance of new absorbtion bands at 610, 630 nm and 660 nm, together with marked colour change 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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Publication details

The article was received on 09 Aug 2017, accepted on 06 Nov 2017 and first published on 09 Nov 2017


Article type: Paper
DOI: 10.1039/C7NJ02957H
Citation: New J. Chem., 2017, Accepted Manuscript
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    Subphthalocyanine basicity: reversible protonation at the azomethine bridge

    Y. Bernhard, V. Lioret and R. A. Decreau, New J. Chem., 2017, Accepted Manuscript , DOI: 10.1039/C7NJ02957H

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