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https://doi.org/10.1021/acs.analchem.6b04974
Title: | Rational Design of a Red-Emissive Fluorophore with AIE and ESIPT Characteristics and Its Application in Light-Up Sensing of Esterase | Authors: | Peng, Lu XU SHIDANG Zheng, Xiaokun Cheng, Xiamin ZHANG RUOYU Liu, Jie LIU BIN Tong, Aijun |
Keywords: | Science & Technology Physical Sciences Chemistry, Analytical Chemistry AGGREGATION-INDUCED-EMISSION ON FLUORESCENT-PROBE LIVING CELLS FAR-RED EMITTING-DIODES CHARGE-TRANSFER STRATEGY VISUALIZATION CHEMOSENSOR INHIBITORS |
Issue Date: | 7-Mar-2017 | Publisher: | American Chemical Society | Citation: | Peng, Lu, XU SHIDANG, Zheng, Xiaokun, Cheng, Xiamin, ZHANG RUOYU, Liu, Jie, LIU BIN, Tong, Aijun (2017-03-07). Rational Design of a Red-Emissive Fluorophore with AIE and ESIPT Characteristics and Its Application in Light-Up Sensing of Esterase. Analytical Chemistr 89 (5) : 3162-3168. ScholarBank@NUS Repository. https://doi.org/10.1021/acs.analchem.6b04974 | Abstract: | The development of red fluorophores with efficient solid-state emission is still challenging. Herein, a red fluorophore 1 with aggregation-induced emission (AIE) and excited-state intramolecular proton transfer (ESIPT) characteristics is rationally designed and facilely synthesized by attaching an electron-donor diethylamine and an electron-acceptor maleonitrile group to salicyladazine. In contrast to many red fluorophores which undergo serious aggregation-caused quenching (ACQ), compound 1 emits bright red fluorescence (em = 650 nm, F = 24.3%) in the solid state with a large Stokes shift of 174 nm. Interestingly, control compounds 2 and 3, which have similar structures as 1, exhibit obvious aggregation-caused quenching (ACQ) characteristics. The difference in the crystal structures of 1, 2, and 3 reveals that the interplanar spacing among molecules plays a decisive role in realizing the AIE characteristics of 1. Moreover, when the hydroxyl group of 1 was substituted by an esterase reactive acetoxyl, a fluorescence light-up probe 4 was developed for sensing of esterase based on the selective reaction between 4 and esterase to generate the AIE and ESIPT active molecule 1. The linear range for in vitro quantification of esterase is 0.01-0.15 U/mL with a detection limit of 0.005 U/mL. Probe 4 was also successfully applied to image esterase in mitochondria of living cells. | Source Title: | Analytical Chemistr | URI: | https://scholarbank.nus.edu.sg/handle/10635/169785 | ISSN: | 0003-2700 1520-6882 |
DOI: | 10.1021/acs.analchem.6b04974 |
Appears in Collections: | Staff Publications Elements |
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