Fluorescent Sensing of Guanine and Guanosine Monophosphate with Conjugated Receptors Incorporating Aniline and Naphthyridine Moieties

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• 作者：Shao-Hung Lu ; Riping Phang ; Jim-Min Fang
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：April 15, 2016
• 年：2016
• 卷：18
• 期：8
• 页码：1724-1727
• 全文大小：349K
• 年卷期：0
• ISSN：1523-7052

文摘

Ethyne-linked naphthyridine–aniline conjugated molecules are selective sensors of decylguanine in dichloromethane and guanosine monophosphate in water (K_ass = 16 000 M^–1). The 2-acetamido-1,8-naphthyridine moiety binds with guanine in a DAA–ADD triply hydrogen-bonded motif. The aniline moiety enhances an electron-donating effect, and the substituent is tuned to attain extra hydrogen bonds, π–π stacking, and electrostatic interactions. The proposed binding modes are supported by a Job plot, ESI-MS, ¹H NMR, UV–vis, and fluorescence spectral analyses.