Binding Sites of Pyrene and Related Compounds and Chiral Excimer Formation in the Cavities of Cyclodextrins and Branched Cyclodextrins

Article abstract of DOI:10.1021/ja00209a033

Circular dicroism (CD) and circularly polarized fluorescence (CPF) spectra reveal the formation of the intermolecular dimer of pyrene having left-handed chirality and intramolecular dimers of 1,3-dinaphtylpropanes having right-handed chiralities in the γ-cyclodextrin cavity.These guest molecules are estimated to be bound to the relatively hydrophobic primary hydroxyl group side of the γ-cyclodextrin cavity, while the more hydrophilic secondary hydroxyl group side is the binding site of the chiral pyrene dimer in the 6-O-α-maltosyl-γ-cyclodextrin cavity because the narrower side of the cavity is capped by the maltosyl group.The pyrene dimer in the branched γ-cyclodextrin exhibits right-handed chirality.