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

作者：Planas Oriol; Fernandez Llaneza Daniel; Nieves Ingrid; Ruiz Gonzalez Ruben; Lemp Else; Zanocco Antonio L; Nonell Santi

来源：Physical Chemistry Chemical Physics, 2017, 19(37): 25537-25543.

DOI：10.1039/c7cp02938a

2-Aminothiazolo[4,5-c] porphycenes are a novel class of 22-pi 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-pi to 18-pi 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.

• 出版日期2017-10-7