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

页码：73 / 76

页数：4

共 50 条

[31] Recent topics of the natural product synthesis by Horner-Wadsworth-Emmons reaction
Kobayashi, Kenichi
Tanaka, Kosaku, III
Kogen, Hiroshi
TETRAHEDRON LETTERS, 2018, 59 (07) : 568 - 582
[32] ASYMMETRIC HORNER-WADSWORTH-EMMONS REACTIONS USING MESO DIALDEHYDES AS SUBSTRATES
KANN, N
REIN, T
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (15): : 3802 - 3804
[33] Solvent-free Horner-Wadsworth-Emmons reaction using DBU
Ando, Kaori
Yamada, Kyohei
TETRAHEDRON LETTERS, 2010, 51 (25) : 3297 - 3299
[34] KINETIC RESOLUTION OF THE ACROLEIN DIMER BY ASYMMETRIC HORNER-WADSWORTH-EMMONS REACTIONS
REIN, T
KANN, N
KREUDER, R
GANGLOFF, B
REISER, O
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1994, 33 (05): : 556 - 558
[35] The Asymmetric Horner-Wadsworth-Emmons Reaction Mediated by an External Chiral Ligand
Grad. Sch. of Pharmaceutical Sci., Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-01, Japan
Angew. Chem. Int. Ed., 4 (515-517):
[36] Synthesis of the Sulfonate Analogue of Seminolipid via Horner-Wadsworth-Emmons Olefination
Franchini, Laura
Compostella, Federica
Colombo, Diego
Panza, Luigi
Ronchetti, Fiamma
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (15): : 5363 - 5366
[37] A NEW PROCEDURE FOR HORNER-WADSWORTH-EMMONS OLEFINATION OF CARBONYL-COMPOUNDS
BONADIES, F
CARDILLI, A
LATTANZI, A
ORELLI, LR
SCETTRI, A
TETRAHEDRON LETTERS, 1994, 35 (20) : 3383 - 3386
[38] STEREOCONTROL IN HORNER-WADSWORTH-EMMONS CONDENSATIONS OF A GEM-DIMETHYLCYCLOPROPYL ALDEHYDE WITH ALPHA-SUBSTITUTED PHOSPHONO ACETATES
HAMMOND, GB
COX, MB
WIEMER, DF
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (01): : 128 - 132
[39] N-Alkylation of α-Iminophosphonates and Application to Horner-Wadsworth-Emmons Reaction
Shimizu, Makoto
Tateishi, Masasato
Mizota, Isao
CHEMISTRY LETTERS, 2014, 43 (11) : 1752 - 1754
[40] Synthesis of unsaturated organotrifluoroborates via Wittig and Horner-Wadsworth-Emmons olefination
Molander, Gary A.
Figueroa, Ruth
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (16): : 6135 - 6140

← 1 2 3 4 5 →