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
  • [1] Synthesis and chiroptical properties of optically active poly(N-propargylamide) bearing photoisornerizable azobenzene moieties
    Zhou, Jing-Lun
    Chen, Xiao-Fang
    Fan, Xing-He
    Lu, Chun-Xiang
    Zhou, Qi-Feng
    JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2006, 44 (20) : 6047 - 6054
  • [2] Synthesis and Properties of Novel Optically Active Platinum-containing Poly(phenyleneethynylene)s
    Otaki, Yoshinori
    Marumoto, Manabu
    Miyagi, Yu
    Hirao, Takehiro
    Haino, Takeharu
    Sanda, Fumio
    CHEMISTRY LETTERS, 2016, 45 (08) : 937 - 939
  • [3] Synthesis and Properties of Novel Optically Active Poly(thiophenyleneethynylene-phenyleneethynylene)s
    Otaki, Yoshinori
    Miyagi, Yu
    Sanda, Fumio
    CHEMISTRY LETTERS, 2015, 44 (07) : 1013 - 1015
  • [4] Synthesis of Novel Optically Active Poly(phenyleneethynylene- aryleneethynylene)s Bearing Hydroxy Groups. Examination of the Chiroptical Properties and Conjugation Length
    Sogawa, Hiromitsu
    Miyagi, Yu
    Shiotsuki, Masashi
    Sanda, Fumio
    MACROMOLECULES, 2013, 46 (22) : 8896 - 8904
  • [5] Synthesis and Photoresponse of Helically Folded Poly(phenyleneethynylene)s Bearing Azobenzene Moieties in the Main Chains
    Sogawa, Hiromitsu
    Shiotsuki, Masashi
    Sanda, Fumio
    MACROMOLECULES, 2013, 46 (11) : 4378 - 4387
  • [6] Synthesis, Chiroptical, and Redox Properties of Ferrocene-Containing Optically Active Polymers
    Sotani, Taichi
    Iwakiri, Hiroko
    Yamada, Hirotaka
    Shimosaraya, Noritaka
    Miyagi, Yu
    Sanda, Fumio
    MACROMOLECULAR MATERIALS AND ENGINEERING, 2019, 304 (09)
  • [7] Synthesis of Optically Active Poly(m-phenyleneethynylene- aryleneethynylene)s Bearing Hydroxy Groups and Examination of the Higher Order Structures
    Sogawa, Hiromitsu
    Shiotsuki, Masashi
    Hirao, Takehiro
    Haino, Takeharu
    Sanda, Fumio
    MACROMOLECULES, 2013, 46 (20) : 8161 - 8170
  • [8] Synthesis of an optically active poly(aryleneethynylene) bearing galvinoxyl residues and its chiroptical and magnetic properties
    Kaneko, Takashi
    Abe, Hiromasa
    Namikoshi, Takeshi
    Marwanta, Edy
    Teraguchi, Masahiro
    Aoki, Toshiki
    SYNTHETIC METALS, 2009, 159 (9-10) : 864 - 867
  • [9] Synthesis and optical properties of poly(2,11-triphenyleneethynylene-alt-m-phenyleneethynylene)s
    Chou, Chingen
    Wang, Degang
    Hsu, Jeffrey F.
    Liu, Yi
    Peng, Zhonghua
    SYNTHETIC METALS, 2009, 159 (15-16) : 1657 - 1663
  • [10] Synthesis and optical properties of novel donor-acceptor poly(phenyleneethynylene)s containing quinoxaline
    Zhang, Li
    Zhang, QiuYu
    Yan, Hongling
    Zhang, JuPing
    Gu, JunWei
    Zhang, HePeng
    Guo, FeiGe
    SYNTHETIC METALS, 2009, 159 (19-20) : 2038 - 2042