A Teflon-Footed Resorcinarene
Shoichi Shimizu, Toshiyuki Kiuchi, Ning Pan · Synfacts · 2007
Significance The authors report the first ‘teflon-footed’ resorcinarene that is soluble in wet fluorous solvents as a result of the formation of a hexameric capsule, which enabled the observation of fluorophobic effects arising from molecular encapsulation in fluorous solvents. The synthetic strategy involved the cyclooligomerization of resorcinol with highly fluorinated aldehyde to give 1 F as a crown conformer in 51% yield. The teflon-footed resorcinarene was insoluble in common organic solvents such as MeOH, EtOAc, CHCl 3 , and n -hexane; however, it was highly soluble in wet perfluorobutyl methyl ether (HFE-7100) and in wet FC-72.