一种三氟甲基取代的含刚性三蝶烯结构二胺合成的研究

Study on synthesis of trifluoromethyl substituted triptycene-containing diamine

从廉价易得的对苯醌和蒽出发,通过D-A加成反应,重排,亲核取代及催化还原等步骤高效合成了一种功能化的聚酰亚胺二胺结构单体。该单体具有三氟甲基及刚性的三蝶烯结构,有望在保持聚酰亚胺良好热力学性能的同时,改善材料的其他性能。该合成路线成功将刚性三蝶烯结构和三氟甲基官能团同时引入到聚酰亚胺单体结构中,从而发挥其协同效应,制得1,4-双(4-氨基-2-(三氟甲基)苯氧基)三蝶烯(BAFPT)。各步反应中间体及BAFPT的结构通过红外光谱和核磁共振得到确认。合成的BAFPT在常规溶剂如四氢呋喃和氯仿中展现了一定的溶解性。在常温条件下,100mg的BAFPT分别在2mL的二甲基甲酰胺(DMF)和二甲基乙酰胺(DMAc)溶液中震荡即能溶解。

Starting from readily available anthracene and p-benzoquinone,functionalized diamine was achieved via D-A addition,rearragement,nucleophilic substitution and catalytic reduction.The synthesized diamine structurally contained trifluoromethyl and rigid triptycene,which was expected to help to maintain the inherent thermal and mechanical performance,and meanwhile to improve the desired practical properties of resultant polyimide materials.This synthetic route involved the dual introduction of both rigid triptycene structure and trifluoromethyl group to the diamine which will display the synergistic effects of the both functional structures.The structure of intermediates and the final diamine BAFPT during the reaction was confirmed by IR,1 H-NMR and 13 C-NMR spectra.The obtained BAFPT was partially solubility in tetrahydrofuran and chloroform.At ambient condition,100 mg of BAFPT was readily dissolved in 2 mL of DMF and DMAc,respectively.