Mechanochemical synthesis of an AIE-TICT-ESIPT active orange-emissive chemodosimeter for selective detection of hydrogen peroxide in aqueous media and living cells, and solid-phase quantitation using a smartphone. (23rd September 2022)

• Record Type: Journal Article
• Authors: Bhosle, Akhil A.; Banerjee, Mainak; Gupta, Varsha; Ghosh, Surajit; Bhasikuttan, Achikanath C.; Chatterjee, Amrita
• Is Part Of: New journal of chemistry. Volume 46:Number 39(2022)
• Page Start: 18961
• Page End: 18972
• Publication Date: 2022-09-23
• Subjects: Chemistry -- Periodicals; Chimie -- Périodiques; 540
• DOI: 10.1039/d2nj03064k
• Languages: English
• ISSNs: 1144-0546

Abstract

Abstract : We report herein the design and mechanochemical synthesis of a chemodosimeter, benzothiazole-derived unsymmetrical azine protected by 4-bromomethylphenylboronic acid (BTPAB ), an orange aggregation-induced emission (AIE), for the selective detection of H2 O2 in a turn-on manner. Abstract : Hydrogen peroxide (H2 O2 ), a signature compound for peroxide explosives, is an important reactive oxygen species (ROS) that plays a crucial role in the physiological processes of organisms. We report herein the design and solventless synthesis of a chemodosimeter, benzothiazole-derived unsymmetrical azine protected by 4-bromomethylphenylboronic acid (BTPAB ), for the selective detection of H2 O2 in a turn-on manner with an orange aggregation-induced emission (AIE). The probe, p -Cl-benzothiazole-diphenyl-azineboronic acid (BTPAB ), was synthesized in four steps from 2-amino thiophenol and a suitably substituted salicylaldehyde derivative by adopting a green route, mechanochemistry. H2 O2 spontaneously cleaves the benzylboronic acid group of BTPAB in 1% DMSO in PBS (10 mM, pH 7.4) medium to produce its precursor BTPA, which emits intense orange AIE and also exhibits photophysical phenomena, namely excited-state intramolecular proton transfer (ESIPT) and twisted intramolecular charge transfer (TICT). The probe was non-responsive to other ROS, cations, anions, and oxidizing and reducing agents. The high sensitivity of BTPAB towards H2 O2 is attributed to a low limit of detection (LOD) of 3.9 × 10 −8 M (1.3 ppb). The practical utility of BTPAB in H2 O2 detection was demonstrated by spiking H2 O2 in water samples collected from local water bodies and in blood serum. BTPAB could efficiently detect intracellular H2 O2 as demonstrated by imaging in live HeLa cells. BTPAB was successfully demonstrated in solid-phase detection of H2 O2 using TLC plates as the platform, a smartphone for image-capture and ImageJ analysis for a practical demonstration of the on-site quantitation of H2 O2 .