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首页> 外文期刊>Chemistry: A European journal >Synthesis of end-functionalized polyacetylenes that contain polar groups by employing well-defined palladium catalysts
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Synthesis of end-functionalized polyacetylenes that contain polar groups by employing well-defined palladium catalysts

机译：通过使用定义明确的钯催化剂合成包含极性基团的末端官能化聚乙炔

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摘要

A series of [(dppf)PdBr(R)]-type complexes (dppf=1,1'- bis(diphenylphosphino)ferrocene; R=p-cyanophenyl (1 a), o-hydroxymethylphenyl (1 b), and triphenylvinyl (1 c)), in combination with silver trifluoromethanesulfonate (AgOTf), were demonstrated to be active for the polymerization of monosubstituted polar acetylene monomers HC≡CCONHC _4H _9 (2), HC≡CCO _2C _8H _(17) (3), HC≡CCH _2OCONHC _6H _(13) (4), HC≡CCH _2OCO _2C _6H _(13) (5), and HC≡CCH(CH _3)OH (6). The yields and molecular weights of the polymers depended on the combination of the Pd catalyst and monomer that was employed. Matrix-assisted laser-desorption/ionization-time of flight (MALDI-TOF) mass spectrometric analysis indicated the formation of polymers that contained the "R" and "H" groups at the chain ends. IR spectroscopic analysis supported the R-end-functionalization of the polymers. NMR spectroscopy and MS identified the presence of species that were formed by single, double, and triple insertion of the monomers into the Pd-C _6H _4-p-CN bond, thereby giving solid evidence for an insertion mechanism for the present system. Density functional theory (DFT) calculations suggested the preference for 1,2-insertion of the monomer compared to 2,1-insertion.
机译：一系列[[dppf）PdBr（R）]型配合物（dppf = 1,1'-双（二苯基膦基）二茂铁; R =对氰基苯基（1a），邻羟基甲基苯基（1b）和三苯基乙烯基（ 1 c））与三氟甲磺酸银（AgOTf）结合使用对单取代极性乙炔单体HC≡CCONHC_4H _9（2），HC≡CCO_2C _8H _（17）（3），HC CHCCH _2OCONHC _6H _（13）（4），HC≡CCH_2OCO _2C _6H _（13）（5）和HC≡CCH（CH _3）OH（6）。聚合物的产率和分子量取决于所使用的Pd催化剂和单体的组合。基质辅助的激光解吸/电离飞行时间（MALDI-TOF）质谱分析表明形成了在链端包含“ R”和“ H”基团的聚合物。红外光谱分析支持聚合物的R-末端官能化。 NMR光谱和MS鉴定了通过单体单次，两次和三次插入Pd-C _6H _4-p-CN键形成的物质的存在，从而为本系统的插入机理提供了坚实的证据。密度泛函理论（DFT）计算表明，与2,1插入相比，单体1,2插入更为可取。

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