Self-Assembly of Daisy Chain Oligomers from Heteroditopic Molecules Containing Secondary Ammonium Ion and Crown Ether Moieties

MALDI-TOF MS of the heteroditopic compound 2-(benzylammoniomethyl)dibenzo-24-crown-8 hexafluorophosphate (4) revealed oligomeric daisy chain species up to the hexamer. Similar results were obtained for 2-(6'-hydroxyhexylammoniomethyl)dibenzo-24-crown-8 hexafluorophosphate (8). The complexations of two substituted dibenzylammonium salts, 2,2'-dimethyldibenzylammonium hexaflurophosphate (9a) and 2,2',5-trimethoxydibenzylammonium hexafluorophosphate (9b), with dibenzo-24-crown-8 were examined as models for slippage systems; association constants are reported for these systems. A crystal structure is reported for the new dimethylbenzylammonoium pseudorotaxane. The trimethoxy analog is shown to be capable of slippage formation of a rotaxane, albeit in low yield. (C) 2010 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 48: 975-985, 2010