Synthesis, Structure, and Characterization of Chromo(fluoro)ionophores with Cation-Triggered Emission Based on N-Methylaza-Crown-Ether Styryl Dyes

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• 作者：Sergey P. Gromov ; Svetlana N. Dmitrieva ; Artem I. Vedernikov ; Nikolay A. Kurchavov ; Lyudmila G. Kuz鈥檓ina ; Sergey K. Sazonov ; Yuri A. Strelenko ; Michael V. Alfimov ; Judith A. K. Howard ; Evgeny N. Ushakov
• 刊名：Journal of Organic Chemistry
• 出版年：2013
• 出版时间：October 4, 2013
• 年：2013
• 卷：78
• 期：19
• 页码：9834-9847
• 全文大小：621K
• 年卷期：v.78,no.19(October 4, 2013)
• ISSN：1520-6904

文摘

Novel 2-benzothiazole-, 4-pyridine-, and 2- and 4-quinoline-based styryl dyes containing an N-methylbenzoaza-15(18)-crown-5(6)-ether moiety were synthesized. A detailed electronic spectroscopy study revealed high performance of these compounds as optical molecular sensors for alkali and alkaline-earth metal cations. They were shown to considerably surpass analogous chromoionophores based on N-phenylaza-crown ethers regarding both the ionochromism and the cation-binding ability. In addition, they act as fluorescent sensors for the metal cations by demonstrating cation-triggered emission. Upon complexation with Ba²⁺, the fluorescence enhancement factor reaches 61. The structural features of dyes and their metal complexes were studied by NMR spectroscopy and X-ray diffraction. The high degree of macrocycle preorganization was found to be one of the factors determining the high cation-binding ability of the sensor molecules based on N-methylbenzoaza-crown ethers.