Novel, Metal-Free, Superacid-Catalyzed “Click” Reactions of Isatins with Linear, Nonactivated, Multiring Aromatic Hydrocarbons
作者:M. Carmen G. Hernandez、Mikhail G. Zolotukhin、Serguei Fomine、Gerardo Cedillo、Salvador L. Morales、Nils Fröhlich、Eduard Preis、Ullrich Scherf、Manuel Salmón、Maria Isabel Chávez、Jorge Cárdenas、Alberto Ruiz-Trevino
DOI:10.1021/ma101048z
日期:2010.9.14
A novel series of linear, high-molecular-weight polymers was synthesized by one-pot, metal-free superacid-catalyzed reaction of isatins (1a−d) with linear, nonactivated, multiring aromatic hydrocarbons: biphenyl (A), p-terphenyl (B), p-quaterphenyl (C), 2-(4-biphenylyl)-6-phenylbenzoxazole (D), 9H-fluorene (E), 9,9-dimethyl-9H-fluorene (F), 2,2′-[2,5-bis(trifluoromethyl)-1,4-phenylene]bis(9,9-dimethyl-9H-fluorene)
一系列新型的线性,高分子量聚合物是通过一锅,无金属超酸催化的靛红(1a - d)与线性,未活化的多环芳烃反应生成的:联苯(A),对-三联苯(B),对-季四苯基(C),2-(4-联苯基)-6-苯基苯并恶唑(D),9 H-芴(E),9,9-二甲基-9 H-芴(F),2 2'-[2,5-双(三氟甲基)-1,4-亚苯基]双(9,9-二甲基-9 H-芴)(G),寡聚9,9-双(2,6-乙基己基) -9 ^ h-芴(H),联苯酚(I)和联-2-萘(J)。该反应在室温下在布朗斯台德超酸三氟甲磺酸(CF 3 SO 3 H,TFSA)中以及在TFSA与二氯甲烷或耐羟基,羧基和氰基的TFA的混合物中进行。获得的聚合物可溶于大多数常见的有机溶剂中,并且可以从溶液中流延出柔性透明膜。合成聚合物的1 H和13 C NMR分析显示,它们的线性结构在主链的亚苯基片段中具有对位取代基。分子量M w和中号Ñ介于54200至