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Issue 37, 2017
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Acid- and hydrogen-bonding-induced switching between 22-π and 18-π electron conjugations in 2-aminothiazolo[4,5-c]porphycenes

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Abstract

2-Aminothiazolo[4,5-c]porphycenes are a novel class of 22-π electron aromatic porphycene derivatives prepared by click reaction of porphycene isothiocyanates with primary and secondary amines with high potential as near-infrared theranostic labels. Herein, the optical and photophysical properties of 2-aminothiazolo[4,5-c]porphycenes have been studied, revealing a strong dependence on hydrogen bond donor solvents and acids. High hydrogen bond donor solvents and acids shift the absorption and fluorescence emission of 2-aminothiazolo[4,5-c]porphycenes to the blue due to a contraction of their aromatic system from 22-π to 18-π electrons. Finally, the aromatic shift has been successfully used to measure the pH using 2-aminothiazoloporphycene-labelled gold nanoclusters, paving the way for the use of these compounds as near infrared pH-sensitive probes.

Graphical abstract: Acid- and hydrogen-bonding-induced switching between 22-π and 18-π electron conjugations in 2-aminothiazolo[4,5-c]porphycenes

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Publication details

The article was received on 04 May 2017, accepted on 27 Aug 2017 and first published on 29 Aug 2017


Article type: Paper
DOI: 10.1039/C7CP02938A
Citation: Phys. Chem. Chem. Phys., 2017,19, 25537-25543
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    Acid- and hydrogen-bonding-induced switching between 22-π and 18-π electron conjugations in 2-aminothiazolo[4,5-c]porphycenes

    O. Planas, D. Fernández-Llaneza, I. Nieves, R. Ruiz-Gonzalez, E. Lemp, A. L. Zanocco and S. Nonell, Phys. Chem. Chem. Phys., 2017, 19, 25537
    DOI: 10.1039/C7CP02938A

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