A bifunctional acridine-based fluorescent sensor: ratiometric sensing of H2PO4− and obvious fluorescence quenching towards HSO4− through a synergistic binding effect of benzimidazolium and urea moieties
| Autor: | Xiaozhi Jiang, Haiqiang Yang, Guohua Gao, Dawei Zhang, Alexandre Martinez, Zhiyun Dong |
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| Rok vydání: | 2013 |
| Předmět: |
Fluorophore
010405 organic chemistry Hydrogen bond Organic Chemistry Inorganic chemistry 010402 general chemistry Photochemistry 01 natural sciences Biochemistry Fluorescence 0104 chemical sciences chemistry.chemical_compound chemistry Drug Discovery Acridine Proton NMR Anion binding Bifunctional Selectivity |
| Zdroj: | Tetrahedron. 69:10457-10462 |
| ISSN: | 0040-4020 |
| DOI: | 10.1016/j.tet.2013.09.083 |
| Popis: | Three tweezer-like fluorescent sensors 1–3 based on acridine fluorophore were designed and synthesized. Anion binding properties of sensors 1–3 were studied by fluorescence, UV–vis, 1H NMR, and HRMS. Results showed that the sensor 1, which bears both benzimidazolium and urea groups as binding sites exhibited better anion sensing performance compared with sensors 2 and 3 containing only one kind of binding sites. Especially, it could be used as a dual-responsive selective fluorescent sensor for both H 2 PO 4 − and HSO 4 − via fluorescent bathochromic-shift and fluorescence quenching, respectively. The unique selectivity of sensor 1 towards H 2 PO 4 − and HSO 4 − could be attributed to the synergistic binding effect of benzimidazolium and urea moieties. In addition, the additional hydrogen bond between –OH in H 2 PO 4 − / HSO 4 − and the N on acridine of sensor 1 also played an important role in improving its anion binding affinities. |
| Databáze: | OpenAIRE |
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