TY - JOUR
T1 - Acid- and hydrogen-bonding-induced switching between 22-π and 18-π electron conjugations in 2-aminothiazolo[4,5-c] porphycenes
AU - Planas, Oriol
AU - Fernández-Llaneza, Daniel
AU - Nieves, Ingrid
AU - Ruiz-Gonzalez, Rubén
AU - Lemp, Else
AU - Zanocco, Antonio L.
AU - Nonell, Santi
N1 - Funding Information:
Financial support for this research was obtained from the Spanish Ministerio de Economía y Competitividad (Grants No. CTQ2013-48767-C3-1-R, CTQ2016-78454-C2-1-R and CTQ2015-71896-REDT). O. P. thanks the European Social Funds and the SUR del DEC de la Generalitat de Catalunya for his predoctoral fellowship (Grant No. 2016 FI_B2_00100).
Publisher Copyright:
© 2017 the Owner Societies.
PY - 2017
Y1 - 2017
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=85030703590&partnerID=8YFLogxK
U2 - 10.1039/c7cp02938a
DO - 10.1039/c7cp02938a
M3 - Article
C2 - 28900638
AN - SCOPUS:85030703590
SN - 1463-9076
VL - 19
SP - 25537
EP - 25543
JO - Physical Chemistry Chemical Physics
JF - Physical Chemistry Chemical Physics
IS - 37
ER -