One‐pot photoinduced synthesis of dansyl containing acrylamide hydrogels and their chemosensing properties

• Published in: Journal of applied polymer science Vol. 136; no. 8
• Main Authors: Uygun, M., Doganci, E., Tasdelen, M. A., Gurek, A. G.
• Format: Journal Article
• Language: English
• Published: Hoboken, USA John Wiley & Sons, Inc 20.02.2019; Wiley Subscription Services, Inc
• Subjects: Acetonitrile; Acrylamide; Charge transfer; Cobalt; dansyl; Fluorescence; heavy metal ion‐sensing; Hydrogels; Lead; Materials science; Mercury (metal); Metal ions; Methylene bisacrylamide; Naphthalene; nitroaromatic compounds; Nitrophenol; Nitrotoluene; Organic chemistry; photoinitiation; Photopolymerization; Polymers; Synthesis; Trinitrotoluene
• ISSN: 0021-8995; 1097-4628
• DOI: 10.1002/app.47096

ABSTRACT Novel fluorescent acrylamide hydrogel containing dansyl moiety (DNS‐gel) was synthesized via free‐radical photopolymerization of acrylamide/N,N′‐methylenebisacrylamide by using dansyl chloride as a photoinitiator. DNS‐gel presented dual‐fluorescence emission when excited at 344 nm in acetonitrile:water (1:1) solvent system due to twisted intramolecular charge transfer between dimethylamino and naphthalene units in the dansyl moiety. Synthesized fluorophore containing gel was utilized as a fluorescent sensor against specific metal ions (Pb2+, Hg2+, Co2+, Cd2+, Mn2+, and Zn2+) and nitroaromatic compounds [1,2‐dinitrobenzene, 2,4,6‐trinitro‐1‐phenol [picric acid (PA)], 4‐nitrophenol, 2,4,6‐trinitrotoluene, 2,4‐dinitrophenol (2,4‐DNP), and 2‐nitrotoluene]. Fluorescence intensity of DNS‐gel was diminished by degrees upon the infusion of metal ions and nitroaromatics. For all compounds, the greatest quenching effectiveness was attained in the presence of Co2+ (72.56%), PA (88.55%), and 2,4‐DNP, suggesting that DNS‐gel could be employed as a potential Co2+, PA, and 2,4‐DNP chemical probes. © 2018 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2019, 136, 47096. Dansyl containing hydrogels as fluorescent sensors are directly prepared by photopolymerization of acrylamide/N,N′‐methylenebisacrylamide using dansyl chloride as a photoinitiator.