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Fluorescent Calixarene Scaffolds for NO Detection in Protic Media
Author(s) -
Ahuja Brij Bhushan,
Vigalok Arkadi
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201813589
Subject(s) - calixarene , conjugated system , fluorescence , monomer , diethylamine , chemistry , polymer , scaffold , photochemistry , combinatorial chemistry , organic chemistry , molecule , biomedical engineering , medicine , physics , quantum mechanics
We present the first fluorescent water‐soluble conjugated calixarene scaffolds that are capable of NO gas detection. Two different scaffolds, one based on a 5,5′‐bicalixarene structure and its isomer bearing two distantly conjugated calixarene moieties, were synthesized. While the fluorescence of both isomers is quenched upon either passing of NO gas or generating it in situ from diethylamine NONOate, the bicalixarene‐based scaffold showed a significantly stronger response. We also present an example of a dye encapsulation strategy to achieve the detection of NO at longer wavelengths than in the parent calixarene host. Finally, a conjugated polymer bearing a 5,5′‐bicalixarene scaffold has also been prepared and demonstrated enhanced sensitivity compared to the monomer due to the molecular wire effect.