Abstract
Flavin is an important class of redox compounds involved in a variety of biological processes including electron transfer, fluorescence characteristics and catalytic activities for oxidative transformations. Supramolecular organogels including flavin units would provide novel functions of organocatalysis and fluorescent properties.
We synthesized a new type of bisflavin, bearing a potential galator unit of 1,2-bis(alkylamido)cyclohexane. Bisflavin were found to gelate polar solvents such as DMSO and DMF. The 1H NMR, IR, and UV-vis analyses of sol-gel-transition revealed that the molecular aggregates are formed through intermolecular hydrogen bonding of amide unit and intermolecular π-stacking of flavin rings. Induced CD peaks corresponding to the absorption peaks for the flavin moiety were observed in DMSO gel. The catalytic activities of these gels as well as mixed gel of bisflavin and 1,2-bis(dodecylamido)cyclohexane were also examined using aerobic hydrogenation of olefins with hydrazine.
