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

• Published in: New journal of chemistry Vol. 46; no. 39; pp. 18961 - 18972
• Main Authors: Bhosle, Akhil A, Banerjee, Mainak, Gupta, Varsha, Ghosh, Surajit, Bhasikuttan, Achikanath C, Chatterjee, Amrita
• Format: Journal Article
• Language: English
• Published: CAMBRIDGE Royal Soc Chemistry 10.10.2022; Royal Society of Chemistry
• Subjects: Aqueous solutions; Charge transfer; Chemistry; Chemistry, Multidisciplinary; Hydrogen peroxide; Oxidation; Physical Sciences; Reducing agents; Science & Technology; Smartphones; Solid phases; Synthesis; Water sampling; CU2; OXIDATIVE STRESS; DESIGN; PROGRESS; CONSTRUCTION; LIQUID; SENSOR; AZINE; TRENDS; FLUORESCENT-PROBE
• ISSN: 1144-0546; 1369-9261
• DOI: 10.1039/d2nj03064k

Hydrogen peroxide (H 2 O 2 ), 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 H 2 O 2 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. H 2 O 2 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 H 2 O 2 is attributed to a low limit of detection (LOD) of 3.9 × 10 −8 M (1.3 ppb). The practical utility of BTPAB in H 2 O 2 detection was demonstrated by spiking H 2 O 2 in water samples collected from local water bodies and in blood serum. BTPAB could efficiently detect intracellular H 2 O 2 as demonstrated by imaging in live HeLa cells. BTPAB was successfully demonstrated in solid-phase detection of H 2 O 2 using TLC plates as the platform, a smartphone for image-capture and ImageJ analysis for a practical demonstration of the on-site quantitation of H 2 O 2 . 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 H 2 O 2 in a turn-on manner.