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Short Note

5-[p-(1-L-Phenylalanyloxy)ethoxyl]phenyl-10,15,20-triphenylporphyrin

by
Hai-yang Liu
1,*,
Xi-ming Hu
1,*,
Yi Liu
1,
Jian Huang
1,
Xiao Ying
2,
Xiao-lan Wei
1 and
Nan Xu
1
1
Department of Applied Chemistry, South China University of Technology, Guangzhou 510640, P. R. China
2
Department of Physics, South China University of Technology, Guangzhou 510640, P. R. China
*
Authors to whom correspondence should be addressed.
Molecules 1999, 4(8), M96; https://doi.org/10.3390/M96
Submission received: 1 June 1999 / Accepted: 2 July 1999 / Published: 20 August 1999
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Versions Notes
Molecules 04 m96 i001
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.

Supplementary materials

Supplementary File 1Supplementary File 2

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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MDPI and ACS Style

Liu, H.-y.; Hu, X.-m.; Liu, Y.; Huang, J.; Ying, X.; Wei, X.-l.; Xu, N. 5-[p-(1-L-Phenylalanyloxy)ethoxyl]phenyl-10,15,20-triphenylporphyrin. Molecules 1999, 4, M96. https://doi.org/10.3390/M96

AMA Style

Liu H-y, Hu X-m, Liu Y, Huang J, Ying X, Wei X-l, Xu N. 5-[p-(1-L-Phenylalanyloxy)ethoxyl]phenyl-10,15,20-triphenylporphyrin. Molecules. 1999; 4(8):M96. https://doi.org/10.3390/M96

Chicago/Turabian Style

Liu, Hai-yang, Xi-ming Hu, Yi Liu, Jian Huang, Xiao Ying, Xiao-lan Wei, and Nan Xu. 1999. "5-[p-(1-L-Phenylalanyloxy)ethoxyl]phenyl-10,15,20-triphenylporphyrin" Molecules 4, no. 8: M96. https://doi.org/10.3390/M96

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