Rational construction of long-wavelength emissive AIE molecules and their application for sensitive and visual detection of HClO

Herein, two small-molecule fluorescent dyes, 2-(4-(diethylamino)-2-((4-(4,4,5,5- tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)oxy)benzylidene)malononitrile (BASM) and ethyl-2-cyano-3-(4-(diethylamino)-2-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)oxy)phenyl)acrylate (BASE) with aggregation...

Full description

Saved in:
Bibliographic Details
Published in:Sensors and actuators. B, Chemical Chemical, 2022-02, Vol.352, p.131024, Article 131024
Main Authors: Xu, Zi Yi, Han, Lei, Wang, Xiao Hu, Chen, Jing Rong, Li, Nian Bing, Luo, Hong Qun
Format: Article
Language:English
Subjects:
AIE characteristics
Charge transfer
Conjugation
Detection of HClO
Emission
Fluorescent dyes
Fluorescent indicators
Long-wavelength emission
Malononitrile
Molecular structure
Oxidation
Practical applications
Selectivity
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Herein, two small-molecule fluorescent dyes, 2-(4-(diethylamino)-2-((4-(4,4,5,5- tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)oxy)benzylidene)malononitrile (BASM) and ethyl-2-cyano-3-(4-(diethylamino)-2-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)oxy)phenyl)acrylate (BASE) with aggregation-induced emission characteristics are facilely synthesized and they were applied for the sensitive and selective detection of hypochlorous acid (HClO). For these novel AIE molecules, intricate structure and enormous π-conjugation system are no longer necessary. Due to the enhanced effect of intramolecular charge transfer and restricted intramolecular rotation, BASM and BASE displayed reinforced and long-wavelength emission in solid states and aggregated states. Moreover, the BASM has been rationally designed as a fluorescent probe of HClO based on the selective reaction between the BASM and HClO which generates a fluorescence efficient cyano iminocoumarin. The BASM displays a wide linear range for HClO from 0.5 to 10 μM and the limit of detection is as low as 6.46 nM. Intriguingly, excess amount (10–50 μM) of HClO causes fluorescence quenching due to a unique oxidation process, also explains the sensitivity and selectivity of BASM towards HClO. Furthermore, probe BASM is successfully employed for several practical applications such as detection of HClO in actual samples, fabrication of paper-based sensors, and fluorescence imaging in living bacteria. [Display omitted] •AIE fluorescent dyes BASM and BASE are synthesized with long-wavelength emission.•These molecules have simple structures and tunable optical properties.•Probe BASM shows good selectivity and sensitivity for HClO detection.•Paper-based sensors are fabricated for on-site visual detection of HClO.•Probe BASM was employed for imaging of exogenous HClO in living bacteria.
ISSN:0925-4005
1873-3077
DOI:10.1016/j.snb.2021.131024