1Department of Applied Chemistry, 2Department of Physics, South China University of technology, Guangzhou 510641, China. (E-mail: [email protected]; [email protected] )
3Department of Chemistry, Hong Kong University of Science and Technology, Hong Kong, China
4Department of Chemistry, Zhongshan University, Guangzhou 510275, China
Received: 10 June 2000 / Accepted: 25 August 2000 / Published: 25 December 2000
5-[o-(2-bromo-1-ethoxy)]phenyl-10,15,20-triphenylporphyrin (1) was prepared according to published method [1]. The mixture of 1 (0.35mmol), L-phenylalanine (2.60mmol), BTEAC (28mg) and anhydrous potassium carbonate (4g) was stirred in DMF (50ml) at room temperature for 72 hours. Reaction mixture was then poured into satured NaCl solution (150ml). The precipitate was filtered and washed several times with water, dried in vacuum. The crude product was purified by chromatography on silica gel. The column was first washed sufficiently with chloroform and then CHCl3:CH3CH2OH (v:v, 1:1) was used as eluent and the second band was collected. The solvent was evaporated to give 0.034g (11.8%) of 5-[o-(1-L-Phenylalanylamino)ethoxyl]phenyl-10,15,20-triphenylporphyrin (2) as a purple solid.
IR (KBr): 3314 (w), 3025 (w), 1594 (m), 1489 (w), 1470 (m), 1440 (m), 1391 (w), 1347 (m), 1307 (w), 1239 (w), 1208 (w), 1180 (w), 1155 (w), 1116 (w), 1068 (m), 1027 (w), 1000 (w), 965 (s), 918 (w), 876 (w), 845 (w), 796 (s), 724 (s), 700 (s), 656 (w), 554 (w), 403 (w).
UV-Vis (DMSO): 418.5, 514.5, 548.9, 589.7, 645.3.
1H-NMR (400 MHz, d6-DMSO/CDCl3, 1:1, V:V): -2.90 (s, 2H, pyrrole NH), 1.18 (m, 1H, C*H), 1.58 (br. s, 1H, CH2), 1.77 (br. s, 1H, CH2), 2.06 (br. s, 1H, NH), 2.24 (br. s, 1H, CH2), 2.55 (br. s, 1H, CH2), 3.90 (br. d, 2H, CH2), 6.04 (br. s, 2H, phenyl of Phe), 6.44 (br. s, 2H, Phenyl of Phe), 6.61(br. s, 1H, phenyl of Phe), 7.30-8.09 (several m, 19H, TPP Ph-H), 8.74 (br. s, 8H, pyrrole -H).
FAB-MS ([M+1]+): 822.
Acknowledgment: This work was supported by the Natural Science Foundation of China and Natural Science Foundation of Guangdong Province.
Reference
1. Ji, L.-N.; Qin X.; Huang J.-W. Acta Scientiarum Natruralium Universitatis Sunyatseni 1993, 32(2), 1.
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