Issue 5, 2020

From simple Katritzky salts to AIEgens: mechanochromic luminescence and heparin detection

Abstract

Developing and exploring efficient fluorophores are of fundamental significance for sensing and tracking chemical or biological species and processes. Herein, a series of novel AIEgens derived from Katritzky pyridinium salts have been readily synthesized via a condensation reaction between their corresponding pyrylium precursors and versatile primary amines such as alkylamine and amino acid derivatives. The model compound TPP1 with a 2,4,6-triphenylpyridinium skeleton showed a smooth AIE curve without an inflection point, and the emission enhancement was attributed to the formation of water clusters around the pyridinium ring and the subsequent nano-aggregate formation, which hindered their intramolecular motions. Moreover, tetraphenylethene moiety-conjugated Katritzky salts retained classical AIE properties and were endowed with larger Stokes shifts and red-shifted emissions. Moreover, all these cationic AIE-active chromophores exhibited obvious mechanofluorochromism behaviors with red-shifted luminescence upon grinding and blue-shifted emission after solvent annealing. The existence of the positively charged pyridinium ring endowed these luminogens with the capability to selectively detect Heparin in aqueous media from other ionic biopolymers.

Graphical abstract: From simple Katritzky salts to AIEgens: mechanochromic luminescence and heparin detection

Supplementary files

Article information

Article type
Research Article
Submitted
26 dec 2019
Accepted
17 mar 2020
First published
18 mar 2020

Mater. Chem. Front., 2020,4, 1492-1499

From simple Katritzky salts to AIEgens: mechanochromic luminescence and heparin detection

F. Lin, Y. Feng, X. Liu, L. Wang, Z. Yu and Y. Liu, Mater. Chem. Front., 2020, 4, 1492 DOI: 10.1039/C9QM00783K

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