(rac)-1,1鈥?Binaphthyl-Based Simple Receptors Designed for Fluorometric Discrimination of Maleic and Fumaric Acids

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• 作者：Kumaresh Ghosh ; Tanushree Sen ; Amarendra Patra ; John S. Mancini ; Justin M. Cook ; Carol A. Parish
• 刊名：Journal of Physical Chemistry B
• 出版年：2011
• 出版时间：July 7, 2011
• 年：2011
• 卷：115
• 期：26
• 页码：8597-8608
• 全文大小：1186K
• 年卷期：v.115,no.26(July 7, 2011)
• ISSN：1520-5207

文摘

(rac)-1,1鈥?Binaphthyl鈥揵ased simple receptors 1 and 2 have been designed, synthesized and studied theoretically. The receptors utilize naphthyridine as the binding motifs for complexation of dicarboxylic acids in CHCl₃. The emission of the BINOL moiety was monitored experimentally to ascertain the selectivity and sensitivity of the receptors. Receptor 1 distinguishes maleic acid from isomeric fumaric acid by exhibiting different fluorescence behavior and demonstrates stronger binding in the excited state. Modulation of the binding sites of 1 leads to a new receptor structure 2, which was found to be less efficient in distinguishing maleic from fumaric acid, fluorometrically. Both 1 and 2 also recognize other hydroxy di- and tricarboxylic acids. The binding interactions were monitored by ¹H NMR, fluorescence and UV鈥搗is spectroscopic methods. Structures of apo-hosts, guests and host鈥揼uest complexes were determined using force-field based conformational searching. Low energy ensembles were grouped into geometrically similar families, and low energy structures from each family were verified using B3LYP/6-31G*/PB-SCRF(CHCl₃) calculations. The atomistic calculations provide insight into the differential dicarboxylic acid binding behavior of receptors 1 and 2.