Synthesis of novel cyclodextrin derivatives by aromatic spacer insertion and their inclusion ability

Novel cyclic host molecules were synthesized by the insertion of three types of aromatic spacers into the skeleton of permethylated alpha-cyclodextrin. These host molecules formed a 1:1 complex with sodium 3- and 4-nitrobenzenesulfonates (3- and 4-NBS), and sodium 2,4-dinitrobenzenesulfonate (DNBS) in D2O/CD3OD (4:1) solution. The type of spacer inserted remarkably affected the inclusion ability of the hosts toward DNBS. The p-xylylene-inserted CDs showed greater inclusion ability toward DNBS than permethylated alpha- and beta-CDs. (c) 2005 Elsevier Ltd. All rights reserved.