標題: Cooperative Recognition of a Copper Cation and Anion by a Calix[4]arene Substituted at the Lower Rim by a beta-Amino-alpha,beta-Unsaturated Ketone
作者: Senthilvelan, Annamalai
ho, I. -Ting
Chang, Kai-Chi
Lee, Gene-Hsiang
Liu, Yi-Hung
Chung, Wen-Sheng
應用化學系
Department of Applied Chemistry
關鍵字: calixarenes;dipolar reactions;ditopic receptor;fluorescence;inclusion compounds
公開日期: 2009
摘要: We report herein a new ditopic calix[4]arene receptor 25,27-bis{[4-amino-4-(1-naphthyl)-2-oxo-3-butenyl]oxy}-26,28-dihydroxycalix[4]arene (2) for the simultaneous complexation of anionic and cationic species. The host molecule 25,27-bis{[3-(1-naphthyl)-5-isoxazolyl]methoxy}-26,28-dihydroxycalix[4]arene (1) was synthesised first and was followed by a [Mo(CO)(6)]mediated ring-opening reaction to give the target receptor 2. The binding properties of ligands 1 and 2 towards metal ions in CH(3)CN were investigated by UV/Vis and fluorescence spectroscopies. The results showed that both ligands I and 2 were highly selective for Cu(II) ions. Upon titration with Cu(II), the fluorescence of I was severely quenched, whereas 2 showed strong fluorescence enhancement because the metal ions help to lock the conformation of the fluorophores. During the complexation of 2 with Cu(II), the Cu(II) was reduced to Cu(I) by the free phenolic OH of 2, whereas the phenol was oxidised by Cu(II), after which it assisted in the trapping of Cu(I). Ditopic behaviour was observed for the complex 2 center dot Cu(I), which showed further enhancement of its fluorescence intensity upon complexation with anions such as acetate or fluoride.
URI: http://hdl.handle.net/11536/7898
http://dx.doi.org/10.1002/chem.200802654
ISSN: 0947-6539
DOI: 10.1002/chem.200802654
期刊: CHEMISTRY-A EUROPEAN JOURNAL
Volume: 15
Issue: 25
起始頁: 6152
結束頁: 6160
顯示於類別:期刊論文


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