Materials and Methods

Cinnamyltriphenylphosphonium chloride, ínm-cinnam-aldehyde, and diphenylhexatriene were obtained from Aldrich Chemical Co., Milwaukee, WI. All solvents used for fluorescence spectroscopic measurements were spectroscopic grade and were obtained from Burdick and Jackson Co., Muskegon, MI. All other solvents were analytical reagent grade. Phospholipids were obtained from Supelco, Bellefonte, PA, and were found to yield a single spot on thin-layer chromatography; they were therefore used without further purification.

Synthesis of Reagents. Cinnamyltriphenylphosphonium chloride (12.4 g, 0.020 mol) was dissolved in 150 mL of freshly prepared 0.2 M sodium methoxide in anhydrous methanol. 4-(Dimethylamino)-íra «í-cinnamaldehyde (4.0 g, 0.031 mol) was added and the solution heated for 1 h at reflux under argon. The orange crystals that formed on cooling to 5 C were filtered, washed with 60% methanolin water, and then dried. The product was crystallized twice from toluene, giving 4.4 g of an orange crystalline solid, mp 159 C. Anal. Caled for C20H2iN: C, 87.27; H, 7.64; N, 5.09. Found: C, 87.41; H, 7.47; N, 4.95 (Galbraith Laboratories, Knoxville, TN). A mixture of 1.0 g of DMA-DPH, 10 mL of methyl iodide, and 100 mL of acetone was refluxed about 16 h with an efficient condenser. The product that separated was washed