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
来源：
MACROMOLECULES | 2011年 / 44卷 / 09期
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
  • [31] Chiral oxazoline substituted optically active poly(m-phenylene)s: Synthesis and coupling polymerizations of (S)-4-benzyl-2-(3,5-dihalidephenyl) oxazoline using transition metal catalysts
    Rattanatraicharoen, Poompat
    Tanaka, Yoko
    Shintaku, Keiko
    Kawaguchi, Takuro
    Yamabuki, Kazuhiro
    Oishi, Tsutomu
    Onimura, Kenjiro
    JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2013, 51 (06) : 1315 - 1322
  • [32] Synthesis and properties of hexafluoroisopropylidene-containing sulfonated poly(arylene thioether phosphine oxide)s for proton exchange membranes
    Gui, Longyong
    Zhang, Chunjie
    Kang, Sen
    Tan, Ning
    Xiao, Guyu
    Yan, Deyue
    INTERNATIONAL JOURNAL OF HYDROGEN ENERGY, 2010, 35 (06) : 2436 - 2445
  • [33] Synthesis, characterization and electrochemical properties of poly(phenoxy-imine)s containing peril and tert-butyl units
    Kaya, Ismet
    Sandal, Bekir Suleyman
    Karaer, Hatice
    JOURNAL OF KING SAUD UNIVERSITY SCIENCE, 2019, 31 (01) : 75 - 82
  • [34] Synthesis and optical properties of poly(N-octyl-m-benzamide)s bearing an oligothiophene chromophore on the benzene ring
    Takagi, Koji
    Nishikawa, Yuma
    Shimizu, Kana
    Yamakado, Ryohei
    Sugimoto, Shinri
    Kondo, Masaharu
    POLYMER JOURNAL, 2016, 48 (05) : 605 - 610
  • [35] Efficient Tuning Nonlinear Optical Properties: Synthesis and Characterization of a Series of Novel Poly(aryleneethynylene)s Co-Containing BODIPY
    Zhu, Mei
    Jiang, Li
    Yuan, Mingjian
    Liu, Xiaofeng
    Ouyang, Canbin
    Zheng, Haiyan
    Yin, Xiaodong
    Zuo, Zicheng
    Liu, Huibiao
    Li, Yuliang
    JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2008, 46 (22) : 7401 - 7410
  • [36] Metathesis polymerization of monomers containing two diphenylacetylene units: synthesis and properties of poly(diphenylacetylene)s bearing diphenylacetylene units on the side chain
    Sakaguchi, Toshikazu
    Shimada, Hikaru
    Hashimoto, Tamotsu
    POLYMER CHEMISTRY, 2020, 11 (40) : 6471 - 6478
  • [37] Precise Synthesis of Poly(fluorene-2,7-vinylene)s Containing Oligo(thiophene)s at the Chain Ends: Unique Emission Properties by the End Functionalization
    Kuwabara, Shingo
    Yamamoto, Nobuhiro
    Sharma, Prabhuodeyara M. Veeresha
    Takamizu, Kenji
    Fujiki, Michiya
    Geerts, Yves
    Nomura, Kotohiro
    MACROMOLECULES, 2011, 44 (10) : 3705 - 3711
  • [38] All-Donor Poly(arylene-ethynylene)s Containing Anthracene and Silole-Based Units: Synthesis, Electronic, and Photovoltaic Properties
    Grisorio, Roberto
    Suranna, Gian Paolo
    Mastrorilli, Piero
    Allegretta, Giovanni
    Loiudice, Anna
    Rizzo, Aurora
    Gigli, Giuseppe
    Manoli, Kyriaki
    Magliulo, Maria
    Torsi, Luisa
    JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2013, 51 (22) : 4860 - 4872
  • [39] Random Poly(fluorenylene-vinylene)s Containing 3,7-Dibenzothiophene-5,5-dioxide Units: Synthesis, Photophysical, and Electroluminescence Properties
    Grisorio, Roberto
    Piliego, Claudia
    Cosma, Pinalysa
    Fini, Paola
    Mastrorilli, Piero
    Gigli, Giuseppe
    Suranna, Gian Paolo
    Nobile, Cosimo Francesco
    JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2009, 47 (08) : 2093 - 2104
  • [40] Synthesis and properties of new side-chain-type poly(arylene ether sulfone)s containing tri-imidazole cations as anion-exchange membranes
    Wang, Chenyi
    Zhou, Yuanpeng
    Xu, Chang
    Zhao, Xiaoyan
    Li, Jian
    Ren, Qiang
    INTERNATIONAL JOURNAL OF HYDROGEN ENERGY, 2018, 43 (45) : 20739 - 20749
1234