Improving inclusion capabilities of permethylated cyclodextrins by appending a cap-like aromatic moiety

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• 作者：M. José ; Gonzá ; lez-Á ; lvarez^a ; Natalia Mayordomo^a ; Laura Gallego-Yerga^b ; ^c ; Carmen Ortiz Mellet^b ; Francisco Mendicuti^a ; ^{francisco.mendicuti@uah.es}
• 关键词：Fluorescence ; Molecular modeling ; Modified cyclodextrins ; Self-aggregation ; Complexation fluorescent probe
• 刊名：Tetrahedron
• 出版年：2012
• 期刊代码：107_00404020
• 类别：ch
• 出版时间：8 April, 2012
• 卷：68
• 期：14
• 页码：2961-2972
• 文件大小：1644 K

摘要

Steady-state and time-resolved fluorescence techniques have been employed in the study of the complexation of methyl 2-naphthalenecarboxylate (2MN), a fluorescent probe, with 2^I,3^I-O-(o-Xylylene)-per-O-Me-伪-, -尾-, and -纬-cyclodextrins (Xm伪-, Xm尾-, and Xm纬CDs, respectively), which have also the capability of self-aggregate. The influence of the xylylene moiety was assessed by comparing the data of 2MN complexation by Xm伪-, Xm尾-, and Xm纬CD with those obtained for their fully permethylated m伪-, m尾-, and m纬CD counterparts. The 2MN emission spectrum shows two overlapping electronic bands whose ratio of intensities, R, is very sensitive to the polarity of the surrounding medium. The stoichiometry, the complex formation constants and the 螖H⁰ and 螖S⁰ parameters upon inclusion were obtained from the variations in R and 銆?em>蟿銆?as a function of CD concentration and temperature. 2MN forms 1:1 stoichiometry complexes with all the CDs. Molecular Mechanics and Molecular Dynamics calculations were performed to simulate the complexation processes in the presence of water, determine their preferred structures, and ascertain the host-guest interactions at play.