期刊
TETRAHEDRON LETTERS
卷 41, 期 35, 页码 6731-6736出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4039(00)01105-9
关键词
calix[4]pyrrole; dimer; cooperative anion binding; C-C bond formation
Calix[4]pyrrole dimers (2, 5, and 6), potential hosts for anionic guests, were synthesized by a procedure involving a palladium(0) catalyzed C-C bond formation process. In the case of 2, a dimer linked via a rigid di-ethynyl spacer, a detailed study of carboxylate anion binding was carried out using H-1 NMR spectroscopy. For isophthalate anion, a 1:1 binding stoichometry was observed with this receptor and a much higher association constant was found than for the control monomer, octamethylcalix[4]pyrrole. These findings are ascribed to cooperative binding. Consistent with this conclusion was the finding that, for phthalate and benzoate anions, 1:2 (host:guest) binding stoichometries and lower association constants were recorded than with isophthalate anion. The control compound, octamethylcalix[4]pyrrole, showed a 1:1 binding stoichometry and a much lower association constant than dimer 2, not just with isophthalate but also phthalate and benzoate anions. (C) 2000 Elsevier Science Ltd. All rights reserved.
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