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One-pot synthesis of a new rhodamine-based dually-responsive pH sensor and its application to bioimaging
Authors:Aifeng Liu  Miaomiao Hong  Wen Yang  Shenzhou Lu  Dongmei Xu
Affiliation:1. College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Ren-ai Road No.199, Suzhou Industrial Park, Suzhou, Jiangsu 215123, China;2. Jiangsu Key Laboratory of Advanced Functional Polymer Design and Application, Soochow University, Suzhou, Jiangsu 215123, China;3. College of Textile and Clothing Engineering, Soochow University, Suzhou, Jiangsu 215123, China
Abstract:A new colorimetric and fluorescent sensor for the highly acidic pH was developed from rhodamine B, 1-(2-aminoethyl)piperazine, and 4-chloro-7-nitro-2,1,3-benzoxadiazole. The sensor could be synthesized in one pot with an 82.5% yield, and for the first time N,N-diisopropylethylamine was found to be crucial for the rhodamine spirolactam formation. The sensor responded to pH rapidly, visibly, reversibly, highly selectively, and sensitively. From pH 7.77 to 2.03, the absorption and fluorescence intensity of the sensor increased by 285 and 50.3 folds, respectively. The pKa value based on the fluorescence titration was 2.87. Fluorescent imaging of living cells treated with the sensor in different pH media indicated that the sensor could provide intracellular pH information.
Keywords:Rhodamine   Colorimetric   Fluorescent   pH   Sensor   Bioimaging
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