Phosphorylated 1,6-diphenyl-1,3,5-hexatriene.
A lipophilic dye consisting of a (1E,3E,5E)-1,6-diphenyl-1,3,5-hexatriene (DPH) fluorophore attached to a phosphate diester was prepared, and its fluorescence behavior in different solvent systems and in a liposomal membrane bilayer was examined. The key step in the synthesis of the functionalized end of the dye is a Sonogashira coupling of protected iodophenol with propargyl alcohol; the remaining phenyl ring and double bonds of the all-trans polyene core arise from a Wittig reaction with trans-cinnamaldehyde. Like DPH itself, the emission intensity of its phosphorylated derivative is quenched in polar media.
Department of Chemistry, East Carolina University, Greenville, NC 27858-4353, USA.
Ling
L
Ma
Jessica C
JC
Morgan
Wendy E
WE
Stancill
William E
WE
Allen
D004161:Diphenylhexatriene / Q000032:analysis / Q000737:chemistry*; D010766:Phosphorylation
D004161:Diphenylhexatriene