Dual-Responsive Excited-State Intramolecular Double-Proton Transfer-Based Optical Probe for Hypochlorite and Picric Acid Detection With Applications in 3D-Printed Indicators, Biosensing, and Theranostics
3D printing; anticancer; biosensor; excited-state intramolecular double-proton transfer; fluorescence
A dual-mode fluorescent probe incorporating aggregation-induced emission (AIE) activity, named 2-((E)-1-(((E)-4-(diethylamino)-2-hydroxybenzylidene)hydrazineylidene)ethyl)naphthalen-1-ol (DHN), was formulated and synthesized for the selective detection of explosive picric acid (PA) and hypochlorite (OCl?) via suppression of the excited-state intramolecular double-proton transfer (ESIDPT) mechanism. A significant fluorescence quenching of DHN at 535 nm was observed upon interaction with both PA and OCl? with the detection limits at 0.012 ?M and 2.34 ?M as well as high quenching efficiencies (Ksv) of 3.811 104 M?1 and 1.164 104 M?1, respectively. To elucidate the sensing behavior, various spectroscopic techniques were employed. Interestingly, DHN exhibited AIE behavior in high water content, showing a red-shifted emission accompanied by a visible fluorescence change from whitish green to yellow. As a novel application, DHN was incorporated into a 3D-printed polymer system, demonstrating its practical utility in detecting PA and OCl?. Further, for biological relevance, the interaction of DHN with OCl? was explored for its cytotoxicity against MCF-7 breast cancer cells and its imaging capability in physiological media. Therefore, we believe that the present work provides a promising direction for the future development of optical-based detection of hypochlorite and picric acid in liquid as well as solid phases. 2026 Wiley-VCH GmbH.
Kumar, Malavika S.; Das, Avijit Kumar; Mathias, Royston; Kumbhakar, Partha; Karan, Gouri; Choudhury, Sujata Maiti
ChemPhotoChem;Volume;10;Issue;4;Article No.;e202600003;
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https://doi.org/10.1002/cptc.202600003 https://www.scopus.com/pages/publications/105036174437?origin=resultslist
Kumar M.S., Department of Chemistry, Christ University, Karnataka, Bangalore, India, Centre for Renewable Energy and Environmental Sustainability, Christ University, Karnataka, Bangalore, India; Das A.K., Department of Chemistry, Christ University, Karnataka, Bangalore, India, Centre for Renewable Energy and Environmental Sustainability, Christ University, Karnataka, Bangalore, India; Mathias R., Department of Physics and Electronics, Christ University, Karnataka, Bangalore, India; Kumbhakar P., Department of Physics and Electronics, Christ University, Karnataka, Bangalore, India; Karan G., Cancer Nanotherapeutics Laboratory, Biochemistry, Molecular Endocrinology, and Reproductive Physiology Division, Department of Human Physiology, Vidyasagar University, Midnapore, India; Choudhury S.M., Cancer Nanotherapeutics Laboratory, Biochemistry, Molecular Endocrinology, and Reproductive Physiology Division, Department of Human Physiology, Vidyasagar University, Midnapore, India