Chain-Growth Horner-Wadsworth-Emmons Condensation Polymerization Initiated with an Aliphatic Aldehyde

被引：2
|
作者：
Sato, Keichiro [1 ]
Goto, Eisuke [1 ]
Ochiai, Yuto [1 ]
Higashihara, Tomoya [1 ]
机构：
[1] Yamagata Univ, Grad Sch Organ Mat Sci, Dept Organ Mat Sci, 4-3-16 Jonan, Yonezawa, Yamagata 9928510, Japan
来源：
JOURNAL OF PHOTOPOLYMER SCIENCE AND TECHNOLOGY | 2019年 / 32卷 / 01期
关键词：
Horner-Wadsworth-Emmons Reaction; Condensation Polymerization; Chain-Growth Polymerization; Low Environmental-load; pi-Conjugated Polymers; CATALYST-TRANSFER POLYCONDENSATION; MOLECULAR-WEIGHT; REGIOREGULAR POLY(3-HEXYLTHIOPHENE); CONJUGATED POLYMERS; ZINCATE-COMPLEX; METAL-FREE; FUNCTIONALIZATION;
D O I：
10.2494/photopolymer.32.73
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 effective initiation for the chain-growth Horner-Wadsworth-Emmons (HWE) condensation polymerization was succeeded by utilizing an aliphatic aldehyde. Due to the higher electrophilicity of the aliphatic aldehyde compared with the aromatic one, the reactivity of the initiation might be accelerated, producing uniform intermediates to result in the formation of well-defined poly(3-(2-ethylhexyl)thienylene vinylene) (P3EHTV). Consequently, P3EHTV possessed the predictable molecular weight and lower molar-mass dispersity (D-M=1.16) value than that of P3EHTV obtained by employing aromatic aldehyde compounds as the initiators. In this polymerization system, neither transition metals nor halogens are utilized to realize low environmental-load synthesis of well-defined pi-conjugated polymers.
引用
收藏
页码：73 / 76
页数：4
相关论文
共 50 条
  • [41] A convenient method for the preparation of chiral phosphonoacetamides and their Horner-Wadsworth-Emmons reaction
    Ordonez, Mario
    Hernandez-Fernandez, Eugenio
    Montiel-Perez, Martin
    Bautista, Rafael
    Bustos, Paola
    Rojas-Cabrera, Haydee
    Fernandez-Zertuche, Mario
    Garcia-Barradas, Oscar
    TETRAHEDRON-ASYMMETRY, 2007, 18 (20) : 2427 - 2436
  • [42] Synthesis of Butenolides via a Horner-Wadsworth-Emmons Cascading Dimerization Reaction
    Everson, Jack
    Kiefel, Milton J.
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (23): : 15226 - 15235
  • [43] Recent Applications of the Horner-Wadsworth-Emmons Reaction to the Synthesis of Natural Products
    Bisceglia, Juan. A.
    Orelli, Liliana R.
    CURRENT ORGANIC CHEMISTRY, 2012, 16 (19) : 2206 - 2230
  • [44] The asymmetric Horner-Wadsworth-Emmons reaction mediated by an external chiral ligand
    Mizuno, M
    Fujii, K
    Tomioka, K
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1998, 37 (04) : 515 - 517
  • [45] Horner-Wadsworth-Emmons reactions as a facile entry to biogenetic key substructures
    Mulzer, J
    Sieg, A
    Brücher, C
    Müller, D
    Martin, HJ
    SYNLETT, 2005, (04) : 685 - 692
  • [46] Anomalous Horner-Wadsworth-Emmons reactions on 3,4-enuloses
    Moradei, OM
    duMortier, CM
    Cirelli, AF
    TETRAHEDRON, 1997, 53 (22) : 7397 - 7402
  • [47] Horner-Wadsworth-Emmons dispersion polymerization for the production of monodisperse conjugated polymer particles under ambient conditions
    Ciftci, Sibel
    Jansen, Felicitas
    Chimisso, Vittoria
    Kler, Joe
    Rahimi, Khosrow
    Kuehne, Alexander J. C.
    POLYMER CHEMISTRY, 2018, 9 (18) : 2428 - 2433
  • [48] Quantum mechanical investigation of the Horner-Wadsworth-Emmons reaction of benzyl pyridyl ketone
    Kim, Jinyoung
    Park, Kwang-Su
    Yeo, Woon-Seok
    Chong, Youhoon
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2008, 29 (06) : 1269 - 1272
  • [49] Development of a Novel Horner-Wadsworth-Emmons Reagent for the Facile Preparation of Mixed Phosphonoacetates
    Nakao, Michiyasu
    Okamoto, Marie
    Isetani, Satoshi
    Imai, Ayato
    Kitaike, Syuji
    Sano, Shigeki
    SYNOPEN, 2025, 09 (01): : 131 - 137
  • [50] Lithium hexafluoroisopropoxide as a mild base for Horner-Wadsworth-Emmons olefinations of epimerizable aldehydes
    Blasdel, Landy K.
    Myers, Andrew G.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 233
12345