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Volume 2004
Issue 1
10.3390/M357
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Short Note

(s)-2,2’-Bis[5-(p-phenyloxyl)-10,15,20-triphenylporphyrin-methyl]-1,1’-binaphthyl

by
Hai-Yang Liu
1,*,
Yao-Wei Li
1,
Tat-Shing Lai
1,3,
Xiao Ying
2,
Jun-Chun Tian
1 and
Guo-bang Gu
1,*
1
Department of Applied Chemistry, South China University of Technology, Guangzhou 510641, China.
2
Department of Applied Physics, South China University of Technology, Guangzhou 510641, China.
3
Department of Chemistry, Hong Kong University of Science and Technology, Hong Kong, China
*
Authors to whom correspondence should be addressed.
Molbank 2004, 2004(1), M357; https://doi.org/10.3390/M357
Submission received: 5 September 2003 / Accepted: 18 September 2003 / Published: 24 February 2004
Versions Notes
Molbank 2004 m357 i001
(s)-2,2’-Bis[Bromomethyl]-1,1’-binaphthyl was prepared via the bromination of (s)-2,2’-dimethyl-1,1’-binaphthyl[1] by N-bromosuccinimide (NBS) in CCl4 with benzoyl peroxide as initiator (yield: 45.0%). The mixture of 2,2’-Bis[bromomethyl]-1,1’-binaphthyl (0.10g, 0.23 mmol), 5-(p-hydroxy)phenyl-10,15,20-triphenylporphyrin (0.73g, 1.16 mmol) and anhydrous potassium carbonate (1g) was stirred in dry DMF (30 mL) for 24 hours at room temperature. Reaction mixture was then poured into saturated NaCl aqueous solution (100 mL). The precipitate was filtered and washed with water, dried in vacuum. The product was purified by chromatography on silica gel with dichloromethane as an eluent. (s)-2,2’-Bis[5-(p-phenoxyl)-10,15,20-triphenylporphyrin-methyl]- 1,1’-binaphthyl was obtained as a purple solid (0.29 g, yield: 81.9%).
1H-NMR (300 MHz, in CDCl3) d(ppm): -2.85 (s, 4H, pyrrole NH), 5.15-5.31 (m, 4H, CH2), 7.16-8.23 (several m, 50 H, Ar-H), 8.70-8.81 (m, 16 H, pyrrole b-H).
IR(KBr) νmax (cm-1): 3312.9 (w), 3052.6 (w), 1597.8 (m), 1557.8 (w), 1505.5 (m), 1471.5 (m), 1440.4 (w), 1400.2 (w), 1349.6 (m), 1287.7 (m), 1223.0 (s), 1174.2 (m), 1108.1 (w), 1072.3 (w), 1001.3 (m), 980.6 (m), 965.8 (s), 845.1 (w), 799.6 (s), 729.6 (s), 700.9 (s), 520.5 (w).
UV-Vis (in CH2Cl2) lmax (nm): 418.1, 515.0, 552.0, 591.1, 647.0.
CD (in CH2Cl2) De (l, nm): -5.0 (285.2 ), -5.0 (395.3 ), +7.1 (418.2).
FAB-MS m/z: 1539.9 [M+H]+.

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3

Acknowledgment

This work was supported by the Natural Science Foundation of China (No.29971011) and Natural Science Foundation of Guangdong Province(No.000489).

Reference

  1. Maigrot, N.; Maigrot, J. P. Synthesis 1985, 317–320.

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MDPI and ACS Style

Liu, H.-Y.; Li, Y.-W.; Lai, T.-S.; Ying, X.; Tian, J.-C.; Gu, G.-b. (s)-2,2’-Bis[5-(p-phenyloxyl)-10,15,20-triphenylporphyrin-methyl]-1,1’-binaphthyl. Molbank 2004, 2004, M357. https://doi.org/10.3390/M357

AMA Style

Liu H-Y, Li Y-W, Lai T-S, Ying X, Tian J-C, Gu G-b. (s)-2,2’-Bis[5-(p-phenyloxyl)-10,15,20-triphenylporphyrin-methyl]-1,1’-binaphthyl. Molbank. 2004; 2004(1):M357. https://doi.org/10.3390/M357

Chicago/Turabian Style

Liu, Hai-Yang, Yao-Wei Li, Tat-Shing Lai, Xiao Ying, Jun-Chun Tian, and Guo-bang Gu. 2004. "(s)-2,2’-Bis[5-(p-phenyloxyl)-10,15,20-triphenylporphyrin-methyl]-1,1’-binaphthyl" Molbank 2004, no. 1: M357. https://doi.org/10.3390/M357

APA Style

Liu, H.-Y., Li, Y.-W., Lai, T.-S., Ying, X., Tian, J.-C., & Gu, G.-b. (2004). (s)-2,2’-Bis[5-(p-phenyloxyl)-10,15,20-triphenylporphyrin-methyl]-1,1’-binaphthyl. Molbank, 2004(1), M357. https://doi.org/10.3390/M357

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