SYNTHESIS AND CHEMISTRY OF PERFLUORO MACROCYCLES

Authors
LIN TY LIN WH CLARK WD LAGOW RJ LARSON SB SIMONSEN SH LYNCH VM BRODBELT JS MALEKNIA SD LIOU CC
Citation
Ty. Lin et al., SYNTHESIS AND CHEMISTRY OF PERFLUORO MACROCYCLES, Journal of the American Chemical Society, 116(12), 1994, pp. 5172-5179
Citations number
42
Categorie Soggetti
Chemistry
Journal title
Journal of the American Chemical Society → ACNP
ISSN journal
00027863
Volume
116
Issue
12
Year of publication
1994
Pages
5172 - 5179
Database
ISI
SICI code
0002-7863(1994)116:12<5172:SACOPM>2.0.ZU;2-I
Abstract
The perfluoro macrocycles perfluoro-18-crown-6, perfluoro-12-crown-4, perfluoro-15-crown-5, perfluorocyclohexano-15-crown-5, perfluorodicycl ohexano-18-crown-6, perfluorodicyclohexano-24-crown-8, and zabicyclo[8 .8.8]hexacosane(perfluorocryptand[222]) have been prepared by carefull y controlled elemental fluorination. Although they are much weaker bas es than their hydrocarbon analogues, these perfluoromacrocycles are ve ry stable materials which should have a number of applications. The cr ystal structures of perfluoro-18-crown-6 and of a perfluorodicyclohexa no-18-crown-6 isomer are reported. Gas-phase studies with several perf luoro crown ethers and with the perfluorocryptand [222] have shown tha t such macrocycles tenaciously bind O-2(-) and F-. Perfluoro crown eth ers and cryptands coordinate anions preferentially over cations. The c ollisionally activated mass spectra of several perfluoro macrocyclic i ons are described.