Synthesis, chiroptical properties of a helical polyacetylene derivative carrying urea moieties

被引:3
作者
Liu, Rui-yuan [1 ]
Zhang, Tong [2 ]
Yang, Xiao-dong [2 ]
Yan, Yi-chen [1 ]
Qu, Jin-qing [2 ]
机构
[1] Southern Med Univ, Sch Pharmaceut Sci, Guangzhou 510515, Guangdong, Peoples R China
[2] S China Univ Technol, Sch Chem & Chem Engn, Guangzhou 510640, Guangdong, Peoples R China
基金
中国国家自然科学基金;
关键词
Anion; Helix; Hydrogen bonding; Polyacetylene; Urea group; PENDANT TERMINAL GROUPS; SUBSTITUTED POLYACETYLENES; CHAIN HELICITY; GLUTAMIC-ACID; AMINO-ACIDS; SIDE-CHAINS; POLY(PHENYLACETYLENE)S; HYDROGEN; POLY(N-PROPARGYLAMIDES); TRANSFORMATION;
D O I
10.1007/s10118-014-1468-z
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
A novel phenylacetylene derivative containing urea groups was synthesized and polymerized with a Rh catalyst to give the corresponding polymer, poly(1) with moderate number-average molecular weights. The poly(1) was soluble in toluene, CHCl3, CH2Cl2, THF, DMF, and DMSO, but insoluble in hexane, diethyl ether and MeOH. The specific rotation and circular dichroism (CD) spectroscopic studies revealed that poly(1) took predominantly one-handed helical structures. The presence of intramolecular hydrogen bonding was confirmed by liquid-state IR spectroscopy. The helicity of poly(1) could be tuned by temperature and anion. The helical conformation of the polymer was stable against Br- but susceptible to F-.
引用
收藏
页码:931 / 940
页数:10
相关论文
共 34 条
[1]   Metal-organic anion receptors: Arranging urea hydrogen-bond donors to encapsulate sulfate ions [J].
Bondy, CR ;
Gale, PA ;
Loeb, SJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (16) :5030-5031
[2]   Synthesis, chain helicity, assembling structure, and biological compatibility of poly(phenylacetylene)s containing L-alanine moieties [J].
Cheuk, Kevin K. L. ;
Li, Bing Shi ;
Lam, Jacky W. Y. ;
Xie, Yong ;
Tang, Ben Zhong .
MACROMOLECULES, 2008, 41 (16) :5997-6005
[3]   Copolymerization of chiral amino acid-based acetylenes and helical conformation of the copolymers [J].
Gao, GZ ;
Sanda, F ;
Masuda, T .
MACROMOLECULES, 2003, 36 (11) :3938-3943
[4]   Synthesis and properties of amino acid-based polyacetylenes [J].
Gao, GZ ;
Sanda, F ;
Masuda, T .
MACROMOLECULES, 2003, 36 (11) :3932-3937
[5]  
Hendrik P., 2009, DALTON T, V22, P4292
[6]   Efficient and simple colorimetric fluoride ion sensor based on receptors having urea and thiourea binding sites [J].
Jose, DA ;
Kumar, DK ;
Ganguly, B ;
Das, A .
ORGANIC LETTERS, 2004, 6 (20) :3445-3448
[7]   Unique hydrogen bonds between 9-anthracenyl hydrogen and anions [J].
Kwon, JY ;
Jang, YJ ;
Kim, SK ;
Lee, KH ;
Kim, JS ;
Yoon, JY .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (15) :5155-5157
[8]   Synthesis and chiroptical properties of L-valine-containing poly(phenylacetylene)s with (A)chiral pendant terminal groups [J].
Lai, LM ;
Lam, JWY ;
Tang, BZ .
JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2006, 44 (06) :2117-2129
[9]   Synthesis, helicity, and chromism of optically active poly(phenylacetylene)s carrying different amino acid moieties and pendant terminal groups [J].
Lai, Lo Ming ;
Lam, Jacky W. Y. ;
Qin, Anjun ;
Dong, Yongqiang ;
Tang, Ben Zhong .
JOURNAL OF PHYSICAL CHEMISTRY B, 2006, 110 (23) :11128-11138
[10]   Functional polyacetylenes [J].
Lam, JWY ;
Tang, BZ .
ACCOUNTS OF CHEMICAL RESEARCH, 2005, 38 (09) :745-754