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Communication | Special issue | Vol 73, No. 1, 2007, pp.209-215
Published online, 17th August, 2007
DOI: 10.3987/COM-07-S(U)35
4,6-Bis(imidazolio)pyrimidine as a New Anion Receptor

Kiyoshi Sato,* Shin-ichiro Takeuchi, Sadao Arai, Motowo Yamaguchi, and Takamichi Yamagishi

*Division of Applied Chemistry, Faculty of Urban Environmental Sciences, Tokyo Metropolitan University, 1-1 Minami-ohsawa, Hachioji, Tokyo 192-0397, Japan


New aryl-oligomer type anion receptors bearing two imidazolium units linked by 6-membered ring aryl spacers at meta-positions have been synthesized. Complexation behavior of the receptors with halide ions (Cl-, Br-, and I-) in DMSO-d6 was investigated by 1H NMR titrations and semi-empirical calculations (MOPAC AM1). Along with the imidazolium C-H protons, the ortho C-H proton of the central aryl unit forms additional hydrogen bond interaction with guest anion. The receptor with pyrimidine unit exhibited significantly improved anion binding properties.