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

Autor:	Rubén Ruiz-González, Oriol Planas, Santi Nonell, Ingrid Nieves, Daniel Fernández-Llaneza, Antonio L. Zanocco, Else Lemp
Rok vydání:	2017
Předmět:	010405 organic chemistry Hydrogen bond Chemistry General Physics and Astronomy Electron 010402 general chemistry Photochemistry 01 natural sciences Fluorescence 0104 chemical sciences Nanoclusters Click chemistry Physical and Theoretical Chemistry High potential
Zdroj:	Physical Chemistry Chemical Physics. 19:25537-25543
ISSN:	1463-9084 1463-9076
DOI:	10.1039/c7cp02938a
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::fe10004619f085d78c83e81b966b5d92 https://doi.org/10.1039/c7cp02938a Zobrazit plný text záznamu