Synthesis, Chiroptical Properties, and Photoresponsiveness of Optically Active Poly(m-phenyleneethynylene)s Containing Azobenzene Moieties

被引:37
|
作者
Sogawa, Hiromitsu [1 ]
Shiotsuki, Masashi [1 ]
Matsuoka, Hideki [1 ]
Sanda, Fumio [1 ]
机构
[1] Kyoto Univ, Grad Sch Engn, Dept Polymer Chem, Nishikyo Ku, Kyoto 6158510, Japan
关键词
INDUCED HELIX FORMATION; CONJUGATED POLYMERS; POLY(PHENYLACETYLENE)S BEARING; AQUEOUS-SOLUTION; SIDE-CHAINS; FOLDAMERS; SYSTEMS; DYNAMICS; LIGHT; ETHYNYLENE)S;
D O I
10.1021/ma200281e
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
The Sonogashira-Hagihara coupling polymerization of 3',5'-diiodo-4'-hydroxy-N-alpha-tert-butoxycarbonyl-D-phenylglycine ethyl-, hexyl-, and laurylamides 1a-c with p-nonsubstituted, cyano, hexyl, and methoxy 3,5-diethynylazobenzenes 2a-d was carried out to obtain optically active novel poly(m-phenyleneethynylene) with M-w values in the range from 6900 to 15 400 in 62-84% yields. CD and UV-vis spectroscopic data indicated that the polymers adopted thermally stable helical conformations in CH2Cl2 and N,N-dimethylformamide. Poly-(1b-2a) further formed a chirally aggregated structure. The azobenzene moieties of the polymers underwent reversible photoisomerization upon UV- and visible-light irradiation, accompanying the changes of the higher-order structures.
引用
收藏
页码:3338 / 3345
页数:8
相关论文
共 40 条
  • [21] Synthesis, characterization and optical properties of poly(aryleneethynylene)s Containing BODIPY
    Bin Liu
    Fang-lin Huang
    Yong-feng Shi
    Zhi-qing Ni
    Ye Lin
    Shou-chun Yin
    Chinese Journal of Polymer Science, 2015, 33 : 1133 - 1139
  • [22] Synthesis, characterization and optical properties of poly(aryleneethynylene)s Containing BODIPY
    Liu, Bin
    Huang, Fang-lin
    Shi, Yong-feng
    Ni, Zhi-qing
    Lin, Ye
    Yin, Shou-chun
    CHINESE JOURNAL OF POLYMER SCIENCE, 2015, 33 (08) : 1133 - 1139
  • [23] Synthesis,Characterization and Optical Properties of Poly(aryleneethynylene)s Containing BODIPY
    Bin Liu
    Fang-lin Huang
    Yong-feng Shi
    Zhi-qing Ni
    Ye Lin
    尹守春
    Chinese Journal of Polymer Science, 2015, 33 (08) : 1133 - 1139
  • [24] Synthesis and photoluminescence properties of heterocycle-containing poly(disubstituted acetylene)s
    Muroga, Tatsuoki
    Sakaguchi, Toshikazu
    Hashimoto, Tamotsu
    POLYMER, 2012, 53 (20) : 4380 - 4387
  • [25] Synthesis and Properties of Poly(p-phenylene ethynylene)s with Oxidation- and Reduction-Sensitive Moieties
    Schroeter, Michael
    Behl, Marc
    Kaiser, Christian
    Lendlein, Andreas
    MACROMOLECULAR CHEMISTRY AND PHYSICS, 2013, 214 (11) : 1215 - 1224
  • [26] A Novel Type of Optically Active Helical Liquid Crystalline Polymers: Synthesis and Characterization of Poly(p-phenylene)s Containing Terphenyl Mesogen with Different Terminal Groups
    Chen, Lie
    Chen, Yiwang
    Yao, Kai
    Zhou, Weihua
    Li, Fan
    Chen, Liping
    Hu, Rongrong
    Tang, Ben Zhong
    JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2009, 47 (18) : 4723 - 4735
  • [27] Synthesis, characterization and photovoltaic properties of random poly(arylene-vinylene)s containing benzothiadiazole
    Colella, Silvia
    Melcarne, Giovanna
    Mazzeo, Marco
    Gigli, Giuseppe
    Grisorio, Roberto
    Suranna, Gian Paolo
    Mastrorilli, Piero
    POLYMER, 2011, 52 (13) : 2740 - 2746
  • [28] Synthesis and chiroptical properties of poly(p-phenylenevinylene-alt-m-phenylenevinylene) bearing (-)-trans-myrtanoxyl groups on the p-phenylene rings
    Li, Xiangfeng
    Li, Chusheng
    Yan, Jiaguo
    Lu, Jiang
    Hang, Hui
    JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2008, 46 (10) : 3336 - 3343
  • [29] Synthesis of novel optically active poly(thiophenyleneethynylenephenylene)s. Effects of chirality competition and cooperation at the side chains on higher order structures
    Miyagi, Yu
    Otaki, Yoshinori
    Takahashi, Yuki
    Sanda, Fumio
    POLYMER, 2017, 130 : 250 - 257
  • [30] Synthesis, characterization, and photoresponsive behavior of a series of azobenzene-containing side-chain poly(ether sulfone)s with various lengths of flexible spacers
    Zhang, Yuxuan
    Pei, Songhao
    Wang, Yongpeng
    Cui, Zengduo
    Li, Na
    Zhu, Ye
    Zhang, Haibo
    Jiang, Zhenhua
    DYES AND PIGMENTS, 2013, 99 (03) : 1117 - 1123