Synthesis of Chiral (-)-Bis(menthylformyl)phenylphosphine Oxide and Its Helix-sense-selective Initiating Function for Radical Photopolymerization

doi:10.3969/j.issn.0251-0790.2012.08.018

Chem. J. Chinese Universities ›› 2012, Vol. 33 ›› Issue (08): 1727.doi: 10.3969/j.issn.0251-0790.2012.08.018

• Organic Chemistry • Previous Articles Next Articles

Synthesis of Chiral (-)-Bis(menthylformyl)phenylphosphine Oxide and Its Helix-sense-selective Initiating Function for Radical Photopolymerization

ZHANG Jia-An, YANG Nian-Fa, YANG Li-Wen, GONG Hang, LIU Yan-Ling

Key Laboratory of Environmentally Friendly Chemistry and Applications of Ministry of Education, College of Chemisty, Xiangtan University, Xiangtan 411105, China

Received:2011-11-11 Online:2012-08-10 Published:2012-08-10

Abstract

Abstract: In order to synthesize chiral bisacylphosphine oxide photoinitiator and investigate its excess one-handed helicity induction ability, (-)-bis(menthylformyl)phenylphosphine oxide was synthesized from P,P-dichlorophenylphosphine and (-)-menthylformic acid. The structure of the compound was confirmed by NMR, MS and elemental analysis. The results showed that (-)-BMPPO had helix-sense-selective ability in the initiating the radical photopolymerization of bulky monomer 1-phenyldibenzosuberyl methacrylate(PDBSMA). Highly isotactic, optically active polymers having a helical conformation with one-handed helicity were obtained. Lower feed ratio of the monomer to initiator and higher polymerization temperature were favorable to the increase of the helix-sense-selectivity. The photopolymerization of PDBSMA in chiral menthol initiated by (2,4,6-trimethylbenzoyl)diphenylphosphine oxide (TPO) was also helix-sense-selective, but the helix-sense-selectivity was less.

Key words: (-)-Bis(menthylformyl)phenylphosphine oxide, Helix-sense-selective, Radical photopolymerization

CLC Number:

O621.3

TrendMD:

ZHANG Jia-An, YANG Nian-Fa, YANG Li-Wen, GONG Hang, LIU Yan-Ling. Synthesis of Chiral (-)-Bis(menthylformyl)phenylphosphine Oxide and Its Helix-sense-selective Initiating Function for Radical Photopolymerization[J]. Chem. J. Chinese Universities, 2012, 33(08): 1727.

References

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Synthesis of Chiral (-)-Bis(menthylformyl)phenylphosphine Oxide and Its Helix-sense-selective Initiating Function for Radical Photopolymerization

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