CN105949442A - 基于（2-氧吲哚-3-亚基）苯并二呋喃-二酮和连噻吩的共轭聚合物的新型聚合方法 - Google Patents

基于（2-氧吲哚-3-亚基）苯并二呋喃-二酮和连噻吩的共轭聚合物的新型聚合方法 Download PDF

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CN105949442A
CN105949442A CN201610203158.8A CN201610203158A CN105949442A CN 105949442 A CN105949442 A CN 105949442A CN 201610203158 A CN201610203158 A CN 201610203158A CN 105949442 A CN105949442 A CN 105949442A
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diketone
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张国兵
刘家庆
郭景华
吕国强
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Hefei University of Technology
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Abstract

本发明公开了一种基于（2‑氧吲哚‑3‑亚基）苯并二呋喃‑二酮和连噻吩的共轭聚合物的新型聚合方法。该制备方法以连噻吩二苯并二吡咯二酮和苯并二呋喃二酮为基础化合物，以酸为催化剂，在氯苯甲苯等溶剂中发生聚合反应，是一种新型的活性聚合方法，能更加高效的制备这类聚合物。该聚合方法设计思路新颖，高效且活性易控制，可应用于众多这类半导体聚合物的制备。该类聚合物的结构式为其中，R1为C8-C24的烷基链，R2为H或者C6-C14烷基链，n≥1。

Description

基于（2-氧吲哚-3-亚基）苯并二呋喃-二酮和连噻吩的共轭聚合物的新型聚合方法
技术领域
本发明涉及有机物聚合物制备领域，具体涉及一种基于(2-氧吲哚-3-亚基)苯并二呋喃-二酮和连噻吩的共轭半导体聚合物的新型聚合方法。
背景技术
近年来，给/受体(D/A)共轭聚合物在有机薄膜晶体管(OTFT)和有机光伏(OPV)中的应用研究逐步引起人们的重视。有文献报道，双(6-溴-1-(2-癸基十四烷基)2-氧吲哚3-亚基)苯并二呋喃-二酮(BIBDF)是一种异靛蓝的衍生物(在异靛蓝结构中引入了苯并二呋喃二酮)，它具有大的稠合芳香环和对称的二维平面结构，可以增加π-π堆积和分子间作用力。在BIBDF结构中心的内酯基团和内酰胺基团使其具有很强的吸电子能力。如果把BIBDF基团引进到D-A共轭聚合物的主干中作为受体单元，聚合物材料就会具有较低的LUMO和HOMO能级，这对于电子和空穴的注入和传输都是有利的。因此是潜在的应用于OTFT器件方面的一类重要的双极性材料。目前制备这类有机半导体聚合物的方法主要通过Stille聚合方法，但这种传统聚合方法具有锡单体有毒性、催化剂有毒性且昂贵、反应条件要求高等问题，本发明设计了一种基于羟醛缩合反应制备(2-氧吲哚-3-亚基)苯并二呋喃-二酮和连二噻吩的共轭半导体聚合物的新型聚合方法。该制备方法以连噻吩二苯并吡咯二酮和苯并二呋喃二酮为基础化合物，以酸为催化剂在适当溶剂中发生聚合反应，这种聚合方法聚合副产物为水，原子利用率高，催化剂无毒，环境友好，有效的规避了传统聚合方法的弊端，是一种具有开发前景的活性聚合方法，能够更加高效的制备这类聚合物。该聚合方法设计思路新颖，高效且活性易控制，可应用于众多这类半导体聚合物的制备。
发明内容
本发明的目的是为了提供一种基于(2-氧吲哚-3-亚基)苯并二呋喃-二酮和连噻吩的共轭聚合物的新型聚合方法。
本发明是通过以下技术方案实现的：
一种基于(2-氧吲哚-3-亚基)苯并二呋喃-二酮和连噻吩的共轭聚合物的新 型聚合方法，其特征在于：以连噻吩二苯并吡咯二酮和苯并二呋喃二酮为单体，以酸为催化剂，在溶剂中，在一定温度下发生聚合反应，聚合得到的聚合物结构式为
其中，R1为C8-C24的烷基链，R2为H或者C6-C14烷基链，n≥1。
所述的连噻吩二苯并吡咯二酮单体的结构式如单体1所示，所述的苯并二呋喃二酮单体的结构式如单体2所示：
所述的催化剂为盐酸、醋酸、甲苯磺酸中的一种或多种混合。
所述的溶剂可以是醋酸、甲苯、氯苯中的一种或多种混合。
所述的反应温度为60℃-130℃。
所述的聚合反应时间为4-72小时。
所述烷基链可选择C12-C24直链或支链烷烃。
本发明的优点是：
本发明涉及一种基于(2-氧吲哚-3-亚基)苯并二呋喃-二酮和连噻吩的共轭聚合物的新型聚合方法，该聚合方法单体易制得，反应条件易达到(对无水无氧要求不严苛)，分子量可以通过催化剂量单体浓度反应时间控制，且因为该聚合反应不需要以三(二亚苄基丙酮)二钯为催化剂，三(邻甲基苯基)磷为配体， 催化剂无毒，副产物为水，原子利用率高，反应成本低，环保高效，有利于这类聚合物的高效制备从而应用于有机薄膜晶体管和有机光伏器件中。
具体实施方式
下面对本发明的实施例作详细说明：本实例在以本发明技术方案为前提下进行实施，结合了详细的实施方式和具体的操作过程，但本发明的保护范围不限于下述的实施例。
对各单体的制备方法进行如下说明：
制备单体1连噻吩二苯并吡咯二酮的合成具体步骤：六溴靛红和连噻吩硼单体可直接购得，六溴靛红和碳酸钾在DMF中与溴化的烷基链反应得到的化合物，再与连噻吩硼单体通过常规的Suzuki交叉偶联反应即可制得单体1，合成路径示意如下：
制备单体2苯并二呋喃二酮的合成步骤：苯并二呋喃二酮单体采用文献方法制得，详细制备方法参见文献报道(Journal of the American Chemical Society,135(33),12168-12171；2013)，单体苯并二呋喃二酮的合成路径示意如下：
实施例1，合成聚合物P1
聚合物P1的合成具体步骤为：在100mL聚合反应管中加入 0.180g(0.123mmol)单体1，和0.023g(0.123mmol)单体2，再加入催化剂0.06g(0.315mmol)甲苯磺酸，用5mL甲苯溶解上述物质后，冰浴下用N2排空气15分钟，120℃密闭反应48小时。将反应冷却至室温，加入200mL甲醇沉淀，过滤固体，分别用甲醇和正己烷索氏提取24小时，再用氯仿索氏提取24小时，最后旋蒸液体，甲醇沉淀得到聚合物，聚合物P1的合成路径示意如下：
实施例2-3
具体步骤同实施例1：在100mL聚合反应管中加入0.123mmol单体1，和0.123mmol单体2，再加入催化剂0.315mmol甲苯磺酸(催化剂量可依据溶剂量和反应时间相应变化)，用5mL甲苯溶解上述物质后，冰浴下用N2排空气15分钟，120℃密闭反应48小时。将反应冷却至室温，加入200mL甲醇沉淀，过滤固体，分别用甲醇和正己烷索氏提取24小时，再用氯仿索氏提取24小时，最后旋蒸液体，甲醇沉淀得到聚合物P2-P3，其具体结构如表1所示。
表1
综上所述，本发明涉及的是一种基于(2-氧吲哚-3-亚基)苯并二呋喃-二酮和连噻吩的共轭聚合物的新型聚合方法。该D-A型共轭聚合物具有双极性，有望获得高的空穴和电子迁移率，应用该聚合方法有望高效环保的制备这类聚合物从而实际应用于大批量生产中。

Claims (6)

1.一种基于(2-氧吲哚-3-亚基)苯并二呋喃-二酮和连噻吩的共轭聚合物的新型聚合方法，其特征在于：以连噻吩二苯并吡咯二酮和苯并二呋喃二酮为单体，以酸为催化剂，在溶剂中，在一定温度下发生聚合反应，聚合得到的聚合物结构式为：
其中，R1为C8-C24的烷基链，R2为H或者C6-C14烷基链，n≥1。
2.根据权利要求1所述的基于(2-氧吲哚-3-亚基)苯并二呋喃-二酮和连噻吩的共轭聚合物的新型聚合方法，其特征在于：所述的连噻吩二苯并吡咯二酮单体的结构式如单体1所示，所述的苯并二呋喃二酮单体的结构式如单体2所示：
3.根据权利要求1所述的基于(2-氧吲哚-3-亚基)苯并二呋喃-二酮和连噻吩的共轭聚合物的新型聚合方法，其特征在于：所述的催化剂为盐酸、醋酸、甲苯磺酸中的一种或多种混合。
4.根据权利要求1所述的基于(2-氧吲哚-3-亚基)苯并二呋喃-二酮和连噻吩的共轭聚合物的新型聚合方法，其特征在于：所述的溶剂可以是醋酸、甲苯、氯苯中的一种或多种混合。
5.根据权利要求1所述的基于(2-氧吲哚-3-亚基)苯并二呋喃-二酮和连噻吩的共轭聚合物的新型聚合方法，其特征在于：所述的聚合反应温度为60℃-130℃。
6.根据权利要求1所述的基于(2-氧吲哚-3-亚基)苯并二呋喃-二酮和连噻吩的共轭聚合物的新型聚合方法，其特征在于：所述的聚合反应时间为4-72小时。
CN201610203158.8A 2016-03-31 2016-03-31 基于（2-氧吲哚-3-亚基）苯并二呋喃-二酮和连噻吩的共轭聚合物的新型聚合方法 Pending CN105949442A (zh)

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