Tzuhn-Yuan Lin, Wen-Huey Lin, Wayne D. Clark
Jun 1, 1994
Citations
0
Influential Citations
31
Citations
Journal
Journal of the American Chemical Society
Abstract
The perfluoro macrocycles perfluoro-18-crown-6, perfluoro-12-crown-4, perfluoro-15-crown-5, perfluoro-cyclohexano-15-crown-5, perfluorodicyclohexano-18-crown-6, perfluorodicyclohexano-24-crown-8, and perfluoro-4,7,13,16,21,24-hexaoxa-1, 10-diazabicyclo[8,8,8] hexacosane(perfluorocryptand [222]) have been prepared by carefully controlled elemental fluorination. Although they are much weaker bases than their hydrocarbon analogues, these perfluoromacrocycles are very stable materials which should have a number of applications. The crystal structures of perfluoro-18-crown-6 and of a perfluorodicyclohexano-18-crown-6 isomer are reported. Gas-phase studies with several perfluoro crown ethers and with the perfluorocryptand [222] have shown that such macrocycles tenaciously bind O[sub 2][sup [minus]] and F[sup [minus]]. Perfluoro crown ethers and cryptands coordinate anions preferentially over cations. The collisionally activated mass spectra of several perfluoro macrocylic ions are described. 38 refs., 8 figs., 4 tabs.