Facile and Versatile Synthesis of End‐Functionalized Poly(phenylacetylene)s: A Multicomponent Catalytic System for Well‐Controlled Living Polymerization of Phenylacetylenes

作者: Tsuyoshi Taniguchi , Takumi Yoshida , Kensuke Echizen , Kokoro Takayama , Tatsuya Nishimura

DOI: 10.1002/ANIE.202000361

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摘要: A rhodium-based multicomponent catalytic system for well-controlled living polymerization of phenylacetylenes has been developed. The is composed readily available and bench-stable [Rh(nbd)Cl]2 , aryl boronic acid derivatives, diphenylacetylene, 50 % aqueous KOH, PPh3 . This offers a method the facile versatile synthesis various end-functionalized cis-stereoregular poly(phenylacetylene)s because components from acids diphenylacetylene were introduced to initiating end polymers. reaction shows typical nature with high initiation efficiency, molecular weight resulting can be controlled very narrow molecular-weight distributions (Mw /Mn =1.02-1.09). experimental results suggest that present higher activity than activities other systems previously reported.

参考文章(68)
Michihiro Miyake, Yoshihiko Misumi, Toshio Masuda, Living Polymerization of Phenylacetylene by Isolated Rhodium Complexes, Rh[C(C6H5)C(C6H5)2](nbd)(4-XC6H4)3P (X = F, Cl) Macromolecules. ,vol. 33, pp. 6636- 6639 ,(2000) , 10.1021/MA000497X
Shohei Kumazawa, Jesus Rodriguez Castanon, Masashi Shiotsuki, Takahiro Sato, Fumio Sanda, Chirality amplification in helical block copolymers. Synthesis and chiroptical properties of block copolymers of chiral/achiral acetylene monomers Polymer Chemistry. ,vol. 6, pp. 5931- 5939 ,(2015) , 10.1039/C5PY00743G
Eiji Yashima, Katsuhiro Maeda, Hiroki Iida, Yoshio Furusho, Kanji Nagai, Helical polymers: synthesis, structures, and functions Chemical Reviews. ,vol. 109, pp. 6102- 6211 ,(2009) , 10.1021/CR900162Q
Miki Murata, Takashi Oyama, Shinji Watanabe, Yuzuru Masuda, Palladium-catalyzed borylation of aryl halides or triflates with dialkoxyborane: A novel and facile synthetic route to arylboronates Journal of Organic Chemistry. ,vol. 65, pp. 164- 168 ,(2000) , 10.1021/JO991337Q
So Won Youn, Rhodium-Catalyzed Tandem Transformations with Organoboron Reagents: Sequential Multiple C-C Bond Formations European Journal of Organic Chemistry. ,vol. 2009, pp. 2597- 2605 ,(2009) , 10.1002/EJOC.200900001
Shin-ichiro Sakurai, Kento Okoshi, Jiro Kumaki, Eiji Yashima, Two-Dimensional Surface Chirality Control by Solvent-Induced Helicity Inversion of a Helical Polyacetylene on Graphite Journal of the American Chemical Society. ,vol. 128, pp. 5650- 5651 ,(2006) , 10.1021/JA061238B
Toshiki Aoki, Takashi Kaneko, Naoki Maruyama, Atsushi Sumi, Masahiko Takahashi, Takashi Sato, Masahiro Teraguchi, Helix-Sense-Selective Polymerization of Phenylacetylene Having Two Hydroxy Groups Using a Chiral Catalytic System Journal of the American Chemical Society. ,vol. 125, pp. 6346- 6347 ,(2003) , 10.1021/JA021233O
Masashi Shiotsuki, Shohei Kumazawa, Naoya Onishi, Fumio Sanda, Molecular weight dependence of helical conformation of amino acid‐based polyphenylacetylenes Journal of Polymer Science Part A. ,vol. 49, pp. 4921- 4925 ,(2011) , 10.1002/POLA.24941
Yasuhisa Kishimoto, Tatsuya Miyatake, Takao Ikariya, Ryoji Noyori, An Efficient Rhodium(I) Initiator for Stereospecific Living Polymerization of Phenylacetylenes Macromolecules. ,vol. 29, pp. 5054- 5055 ,(1996) , 10.1021/MA960180Q