Synthesis and solution self-assembly behavior study of bay-site double bond functionalized perylene diimide
A new perylene diimide derivative called 1,7-vinyl-PDI-EH was synthesized,containing a double bond at the bay site and a swallow-tailed side chain at the imide site.The reaction conditions were optimized,and the highest yield of 1,7-vinyl-PDI-EH was achieved at a concentration of 3.5 mg/ml in HPLC-grade tetrahydrofu-ran with a reaction time of 2 hours.The photophysical properties and solution self-assembly behavior were charac-terized using UV-Vis and fluorescence spectroscopy.As the concentration increased above 1.1×10-4 mol/L in chloroform solution,fluorescence quenching was observed,with the self-assembly concentration of 1,7-vinyl-PDI-EH determined to be 7.0×10-4 mol/L.Crystals of 1,7-vinyl-PDI-EH were obtained using a double-diffusion method in a chloroform/methanol system and exhibited fluorescence in the crystalline state.
perylene diimidebay-site substitutiondouble bond functionalizedsynthesischaracterizationsolu-tion self-assembly