5-[o-(1-L-Phenylalanylamino)ethoxyl]phenyl-10,15,20-triphenylporphyrin
by
,
Hai-yang Liu
1,*
,
Xi-ming Hu
1,*,
Xiao Ying
2,
Zhong-ping Yao
3,
Jin-wang Huang
1 and
Liang-nian Ji
4,* 1
Department of Applied Chemistry, South China University of technology, Guangzhou 510641, China
2
Department of Physics, South China University of technology, Guangzhou 510641, China
3
Department of Chemistry, Hong Kong University of Science and Technology, Hong Kong, China
4
Department of Chemistry, Zhongshan University, Guangzhou 510275, China
*
Authors to whom correspondence should be addressed.
Molecules 2000, 5(12), M173; https://doi.org/10.3390/M173
Submission received: 10 June 2000
/
Accepted: 25 August 2000
/
Published: 25 December 2000
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
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.
References
- Ji, L.-N.; Qin, X.; Huang, J.-W. Acta Scientiarum Natruralium Universitatis Sunyatseni 1993, 32(2), 1.
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MDPI and ACS Style
Liu, H.-y.; Hu, X.-m.; Ying, X.; Yao, Z.-p.; Huang, J.-w.; Ji, L.-n. 5-[o-(1-L-Phenylalanylamino)ethoxyl]phenyl-10,15,20-triphenylporphyrin. Molecules 2000, 5, M173. https://doi.org/10.3390/M173
AMA Style
Liu H-y, Hu X-m, Ying X, Yao Z-p, Huang J-w, Ji L-n. 5-[o-(1-L-Phenylalanylamino)ethoxyl]phenyl-10,15,20-triphenylporphyrin. Molecules. 2000; 5(12):M173. https://doi.org/10.3390/M173
Chicago/Turabian StyleLiu, Hai-yang, Xi-ming Hu, Xiao Ying, Zhong-ping Yao, Jin-wang Huang, and Liang-nian Ji. 2000. "5-[o-(1-L-Phenylalanylamino)ethoxyl]phenyl-10,15,20-triphenylporphyrin" Molecules 5, no. 12: M173. https://doi.org/10.3390/M173
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