5-[p-(1-L-Phenylalanyloxy)ethoxyl]phenyl-10,15,20-triphenylporphyrin
Hai-yang Liu1*, Xi-ming Hu1*, Yi Liu1, Jian Huang1, Xiao Ying2, Xiao-lan Wei1 and Nan Xu1
1Department of Applied Chemistry, 2Department of Physics, South China University of Technology, Guangzhou 510640, P. R. China. Tel. +86-20-87112991(E-mail: [email protected])
Received: 1 June 1999 / Accepted: 2 July 1999 / Published: 20 August 1999
5-[p-(2-Bromo-1-ethoxy)]phenyl-10,15,20-triphenylporphyrin (1) was prepared by previously published method [1]. L-phenylalanine was chrom. pure. Chloroform (A.R. grade) was dried with P2O5 and distilled before use. Silica gel was C.P. grade (10-40 m). Other reagents were A.R. grade chemicals as supplied. The mixture of 1 (0.27mmol), L-phenylalanine (2.42mmol), BTEAC (25mg) and anhydrous potassium carbonate (4g) was stirred in DMF (50ml) at room temperature for 72 hours. Reaction mixture was then poured into saturated NaCl solution (150ml). The precipitate was filtered and washed several times with water. Product was then purified by means of chromatography on silica gel with chloroform as an eluent. Purple solid 5-[p-(1-L-phenylalanyloxy)ethoxyl]phenyl-10,15,20-triphenylporphyrin (2) was obtained, 0.122g. Yield: 55%.
IR (KBr): 3322.8, 3056.7, 3027.7, 2923.6, 2854.2, 2705.7, 2605.4, 2534.0, 1814.7, 1737.6 (C=O), 1631.5, 1602.6, 1562.1, 1506.2, 1471.4, 1442.5, 1402.0, 1349.9, 1284.4, 1243.9, 1222.7, 1178.3, 1112.7, 1074.2, 966.2, 929.5, 846.6, 800.3, 734.8, 702.0, 648.0, 555.4, 528.4.
UV-Vis l max (nm): 419.1, 516.1, 551.3, 591.5, 648.5.
1H-NMR (CDCl3): -2.77 (s, 2H, pyrrole NH), 1.75 (br. s, 2H, -NH2), 3.06 (m, 1H, CH2), 3.21 (m, 1H, CH2), 3.91 (t, 1H, C*H), 4.40 (m, 2H, -CH2-), 4.65 (m, 2H, -CH2-), 7.24-8.22 (several m, 24H, Ph-H), 8.85 (m, 8H, pyrrole b-H ).
FAB-MS ([M+1]+): 822.
Anal. calc. for C55H43N5O3 (821): C 80.39, H 5.24, N 8.53; found: C 80.21, H 5.13, N 8.46.
Acknowledgment: This research was supported by the 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.
Sample Availability: Available from the authors and from MDPI. MDPI 17056.
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