Selectivity of a Resorcinarene Host for Pentanol Isomers

The resorcinarene host H=1⁴,1⁶,5⁴,5⁶-tetrahydroxy-2,4,6,8-tetrapentyl-3⁴,3⁶,7⁴,7⁶-tetra(p-toluenesulfonyloxy)-1,3,5,7(1,3)-tetrabenzenacyclooctaphane was found to form inclusion compounds with seven pentanol isomers, namely 1-pentanol (H·2(1PENT)), 2-pentanol (H·2(2PENT)), 3-pentanol (H·2(3PENT)), 2-methyl-1-butanol (H·2(2M1B)), 3-methyl-1-butanol (H·2(3M1B)), 2-methyl-2-butanol (H·2(2M2B)) and 3-methyl-2-butanol (H·2(3M2B)). These compounds were characterized by thermal analysis, which showed that they all have host-guest (H:G) ratios of 1:2, and their structures were elucidated and compared. Competition experiments were carried out to investigate the selectivity of this host for some of the pentanol guests and thereby investigate the capability of this host for the separation of pentanol isomers.