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

Oriol Planas, Daniel Fernández-Llaneza, Ingrid Nieves, Rubén Ruiz-Gonzalez, Else Lemp, Antonio L. Zanocco, Santi Nonell

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6 Cites (Scopus)

Resum

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.

Idioma originalAnglès
Pàgines (de-a)25537-25543
Nombre de pàgines7
RevistaPhysical Chemistry Chemical Physics
Volum19
Número37
DOIs
Estat de la publicacióPublicada - 2017

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