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A new porous organic polymer containing Tröger's base units: Evaluation of the catalytic activity in Knoevenagel condensation reaction
Reactive & Functional Polymers ( IF 5.1 ) Pub Date : 2021-07-27 , DOI: 10.1016/j.reactfunctpolym.2021.104998
Fidel E. Rodríguez-González 1 , Vladimir Niebla 1 , M.V. Velázquez-Tundidor 1 , Luis H. Tagle 1 , Rudy Martin-Trasanco 2 , Deysma Coll 3, 4 , Pablo A. Ortiz 3 , Néstor Escalona 5, 6 , Edwin Pérez 7 , Ignacio A. Jessop 8 , Claudio A. Terraza 1, 9 , Alain Tundidor-Camba 1, 9
Affiliation  

The classic Tröger's base polymerization of a diamine and dimethoxymethane with trifluoroacetic acid as catalyst generated a Tröger's base-type polymer (TBP), which exhibited the absolute insolubility in a variety of organic solvents because of its highly aggregated model. A new porous organic polymer was obtained by a simple Tröger's base polymerization reaction between a diamine and formaldehyde in the form of acetal in the presence of trifluoroacetic acid as catalyst. Tröger's base-type polymer (TBP) resulted insoluble in a wide range of organic solvents due to its rigid and aromatic structure. TBP was characterized spectroscopically (FT-IR), thermally and morphologically. As result, a thermostable and amorphous polymer bearing pores ranging between 50 and 300 nm and macro-voids of up to 12 μm was obtained. Due to the insolubility of the TBP, it was tested as a metal-free heterogeneous catalyst in the Knoevenagel condensation reaction, showing a high efficiency. For this, the optimal catalyst load, reaction time and reuse of the catalyst were studied using benzaldehyde and malononitrile as substrates. Furthermore, aldehydes with variable chain sizes and ethyl cyanoacetate replacing malononitrile were tested as substrate with a high percent of conversion (97–99%).



中文翻译:

含有 Tröger 基本单元的新型多孔有机聚合物:Knoevenagel 缩合反应催化活性评价

经典的 Tröger 碱聚合二胺和二甲氧基甲烷,以三氟乙酸为催化剂生成 Tröger 碱型聚合物 ( TBP ),由于其高度聚合模型,该聚合物在多种有机溶剂中表现出绝对不溶性。在三氟乙酸作为催化剂的存在下,二胺和甲醛以缩醛形式进行简单的 Tröger 碱聚合反应,获得了一种新型多孔有机聚合物。Tröger 的碱型聚合物 ( TBP ) 由于其刚性和芳香结构而无法溶于多种有机溶剂。TBP通过光谱(FT-IR)、热学和形态学表征。结果,获得了具有 50 到 300 nm 范围内的孔隙和高达 12 μm 的大空隙的热稳定和无定形聚合物。由于TBP的不溶性,它在 Knoevenagel 缩合反应中作为无金属多相催化剂进行测试,显示出高效率。为此,使用苯甲醛和丙二腈作为底物研究了催化剂的最佳负载量、反应时间和催化剂的再利用。此外,测试了具有可变链大小的醛和取代丙二腈的氰基乙酸乙酯作为具有高转化率 (97-99%) 的底物。

更新日期:2021-08-07
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