CN109232520A - 5,5’-二(苯乙烯基)-3,3’-联二噻吩衍生物、合成方法及其应用 - Google Patents

5,5’-二(苯乙烯基)-3,3’-联二噻吩衍生物、合成方法及其应用 Download PDF

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CN109232520A
CN109232520A CN201811279291.7A CN201811279291A CN109232520A CN 109232520 A CN109232520 A CN 109232520A CN 201811279291 A CN201811279291 A CN 201811279291A CN 109232520 A CN109232520 A CN 109232520A
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殷燕
裴可可
张华�
王媛
孙越
赵连花
潘万勇
张青林
郭会峰
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Shanghai Institute of Technology
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Abstract

本发明公开了一种5,5’‑二(苯乙烯基)‑3,3’‑联二噻吩衍生物、合成方法及其应用。本发明的5,5’‑二(苯乙烯基)‑3,3’‑联二噻吩衍生物通过5,5’‑二醛基‑3,3’‑联二噻吩与芳基苄溴类wittig试剂反应制备得到。本发明合成方法简单、环保，得到的联二噻吩衍生物具有良好的光学性能，可作为有机小分子光电材料，用于有机染料、染料敏化太阳能电池、有机发光二极管、有机场效应晶体管和有机半导体材料领域。

Description

5,5’-二(苯乙烯基)-3,3’-联二噻吩衍生物、合成方法及其 应用
技术领域
本发明涉及有机合成技术领域，具体的说，涉及5,5’-二(苯乙烯基)-3,3’-联二噻吩衍生物、合成方法及其应用。
背景技术
随着光电材料研究的迅猛发展，噻吩类化合物因其掺杂后具有良好的稳定性、易修饰等特点，受到了广泛的关注。其中，具有对称结构的3,3’-联二噻吩衍生物能够实现对噻吩骨架上电子双向传输能力的有效调控，同时延伸了噻吩环上π键的有效共轭长度。此外，其光谱响应带宽阔、摩尔消光系数高，能够实现对光子的有效吸收，因而在光电材料方面应用广泛。
2015年，王华课题组报道了1,3-茚二酮与4-(噻吩-2-基)-苯甲醛缩合产生新的发光体2-[4-(噻吩-2-基)亚苄基]-2H-茚-1,3-二酮,该产物的固体粉末在620nm发出强烈的红光,其荧光量子效率为12.8％,因而可作为用作固态红色荧光材料。(式-1，DyesPigments 2015；115:166-71)。
王华等人报道了5,5’-二辛基-2,2’-联二噻吩并[2,3-b:3’,2’-d]噻吩的合成和光学性能做了研究。该化合物可制成高稳定性、高迁移率的有机半导体材料。(式-2，Journal of Henan University(Natural Science),2011,41(3),262)。
中科院长春应化所的王鹏等人合成了以4,4-二己基-4H-环戊[2,1-b:3,4-b']二噻吩为单元的有机染料敏化太阳能材料。(式-3，J.Phys.Chem.B 2010,114:4461-4464.)。
沈平等报道了可作为染料敏化太阳能电池的4个有机化合物(式-4，Dyes andPigments,2012,92,1042)。
发明内容
本发明的目的在于提供一种5,5’-二(苯乙烯基)-3,3’-联二噻吩衍生物、合成方法及其应用。其合成方法简单、环保，得到的5,5’-二(苯乙烯基)-3,3’-联二噻吩衍生物具有良好光学性能，可作应用于有机染料、染料敏化太阳能电池、有机发光二极管、有机场效应晶体管和有机半导体材料领域。
本发明的技术方案具体介绍如下。
本发明提供一种5,5’-二(苯乙烯基)-3,3’-联二噻吩衍生物，其具有通式Ⅰ所示的结构：
其中，R选自氢，甲基，溴甲基，甲氧基，苯甲氧基，氟，氯，溴，碘，氰基，硝基，氨基，苯基，叔丁基，三氟甲基，羧基，羟基，磺酸基，甲砜基或甲酸甲酯基等其中任意一种。
本发明还提供一种上述5,5’-二(苯乙烯基)-3,3’-联二噻吩的衍生物的合成方法，其通过5,5’-二醛基-3,3’-联二噻吩与芳基苄溴类wittig试剂反应制备得到，其中：芳基苄溴类wittig试剂的结构式为
优选的，碱采用K2CO3、NaCO3、CH3COOK、NaOH、KOH、CH3CH2ONa、CH3COONa、DBU或n-BuLi中任意一种。溶剂采用Et2O、THF、CHCl3、CH2Cl2中任意一种。最优选的条件为：碱为DBU；溶剂为CH2Cl2；DBU、芳基苄溴类wittig试剂和5,5’-二醛基-3,3’-联二噻吩的摩尔比为1.5～2.5：2.3：1。
本发明进一步提供一种上述5,5’-二(苯乙烯基)-3,3’-联二噻吩的衍生物在有机染料、染料敏化太阳能电池、有机发光二极管、有机场效应晶体管和有机半导体材料领域的应用。
和现有技术相比，本发明的有益效果在于：
(1)化合物的合成方法较简单，涉及的药品均为商品化的产品，方便易得且价格低廉。
(2)5,5’-二(苯乙烯基)-3,3’-联二噻吩衍生物具有光稳定性好、光谱响应带宽、摩尔消光系数高，合成容易等特点。可应用于有机小分子光电材料领域。
附图说明
图1为实施例3的荧光谱图。
图2为实施例14的荧光谱图。
具体实施方式
本发明各实施例中用到的二氯甲烷、DBU、4-氰基苄溴等药品和试剂均购买自上海思域化工科技有限公司。
本发明各实施例中所用的设备及生产厂家的信息如下：
搅拌器为：上海梅颖浦MYPII-2恒温磁力搅拌器；
循环水泵为：上海豫康循环多用真空泵SHB-IIIA；
旋转蒸发仪为：上海豫康旋转蒸发仪W.S 206B；
油泵为：上海豫康2XZ-2型旋片式真空泵；
紫外检测器：上海凤凰科仪UV1900；
荧光检测器：日立荧光Hitachi F-4600。
实施例合成步骤如下：100mL的烧瓶中依次加入5,5’-二醛基-3,3’-联二噻吩(1.08mmol)，取代苄溴的wittig试剂(2.48mmol)，DBU(1.62～2.70mmol)和氯仿(20mL)，体系升温回流反应。TLC检测确定原料反应完全。然后滴加少量盐酸淬灭反应，氯仿(3×10mL)萃取，10％的碳酸氢钠溶液洗涤，分液后有机层用无水硫酸钠干燥处理并蒸馏浓缩得到粗产品。硅胶柱层析得纯产品(展开剂为不同比例的二氯甲烷和石油醚混合液)。化学反应方程式如下：
UV-vis的具体操作为：将每个化合物配制成浓度为10-5M的氯仿稀溶液，用2支容积为3ML内径宽度为1cm的石英比色皿分别装入2/3体积的氯仿空白对照样和待测样，将其放入已经基线校准后的紫外检测器中。设置光谱扫描范围为200-500nm，扫描步长为1nm，然后选择开始，待扫描完成后保存相应的谱图并做好记录。
荧光检测器的具体操作为：打开检测器电源，让仪器预热15min，打开氘灯，根据UV-vis测试的谱图信息设置相应的激发波长。将每个化合物配制成浓度为10-5M的氯仿稀溶液，用1支容积为3ML内径宽度为1cm的石英比色皿装入不多于2/3体积的待测样，放入检测器中，然后选择扫描发射光谱并设置对应的激发波长，待扫描完成后再用最大的发射波长回扫激发光谱，重复上述操作直到对应的最大激发波长和发射波长无差别为止。
实施例1
化合物2k，5,5’-二(4-硝基-苯乙烯基)-3,3’-联二噻吩
实施例2
化合物2j，5,5’-二(4-氰基-苯乙烯基)-3,3’-联二噻吩
高分辨质谱理论值：420.0831，实测值：420.0828。
实施例3
化合物2o，5,5’-二(4-三氟甲基-苯乙烯基)-3,3’-联二噻吩
高分辨质谱理论值：506.0619，实测值：506.0621.
1H NMR(500MHz,CDCl3,ppm)δ7.536(d,J＝8.0Hz,4H),7.417(d,J＝8.0Hz,4H),7.003(d,J＝9.0Hz,4H),6.682(d,J＝12Hz,2H),6.526(d,J＝12Hz,2H),
13C NMR(125MHz,CDCl3,ppm)δ140.81,139.67,136.22,129.23,127.92,127.49,125.50,125.47,125.44,124.59,120.49.
图1为实施例3的荧光谱图。
荧光光谱最大发射波长：436nm。
荧光值：46800。
摩尔消光系数：25410M-1·cm-1。
实施例4
化合物2d，5,5’-二(4-甲氧基-苯乙烯基)-3,3’-联二噻吩
高分辨质谱理论值：430.1112，实测值：430.1114。
实施例5
化合物2l，5,5’-二(4-氨基-苯乙烯基)-3,3’-联二噻吩)
高分辨质谱理论值：400.1121，实测值：400.1119。
实施例6
化合物2p，5,5’-二(4-甲砜基-苯乙烯基)-3,3’-联二噻吩
高分辨质谱理论值：526.0402，实测值：526.0405。
实施例7
化合物2g，5,5’-二(4-氯-苯乙烯基)-3,3’-联二噻吩
高分辨质谱理论值：438.0135，实测值：438.0138。
实施例8
化合物2h，5,5’-二(4-溴-苯乙烯基)-3,3’-联二噻吩
高分辨质谱理论值：525.9110，实测值：525.9109。
实施例9
化合物2i，5,5’-二(4-碘-苯乙烯基)-3,3’-联二噻吩
高分辨质谱理论值：621.8804，实测值：621.8803。
实施例10
化合物2b，5,5’-二(4-甲基-苯乙烯基)-3,3’-联二噻吩
高分辨质谱理论值：398.1207，实测值：398.1209。
实施例11
化合物2a，5,5’-二(苯乙烯基)-3,3’-联二噻吩
高分辨质谱理论值：370.0825，实测值：370.0823。
实施例12
化合物2e，5,5’-二(4-苯甲氧基-苯乙烯基)-3,3’-联二噻吩)
高分辨质谱理论值：554.1401，实测值：554.1399。
实施例13
化合物2m，5,5’-二(4-苯基-苯乙烯基)-3,3’-联二噻吩
高分辨质谱理论值：522.1511实测值：522.1510。
实施例14
化合物2n，5,5’-二(4-叔丁基-苯乙烯基)-3,3’-联二噻吩)
高分辨质谱理论值：482.2131，实测值：482.2129。
1H NMR(500MHz,CDCl3,ppm)δ7.367(d,J＝8.0Hz,4H),7.316(d,J＝8.5Hz,4H),7.084(d,J＝1.5Hz,2H),7.023(d,J＝1.5Hz,2H),6.626(d,J＝12Hz,2H),6.579(d,J＝12Hz,2H),
13C NMR(125MHz,CDCl3,ppm)δ150.84,140.47,136.33,134.05,129.72,128.48,126.78,125.40,122.65,119.64,34.64,31.35。
图2为实施例14的荧光谱图。
荧光光谱最大发射波长：439nm。
荧光值：27500。
实施例15
化合物2c，5,5’-二(4-溴甲基-苯乙烯基)-3,3’-联二噻吩
高分辨质谱理论值:553.9411，实测值：553.9410。
实施例16
化合物2f，5,5’-二(4-氟-苯乙烯基)-3,3’-联二噻吩
高分辨质谱理论值：406.0720，实测值：406.0719。
实施例17
化合物2r，5,5’-二(4-甲酸甲酯基-苯乙烯基)-3,3’-联二噻吩
高分辨质谱理论值：486.1012，实测值：486.1015。
实施例18
化合物4,4’-二(4-羧基-苯乙烯基)-3,3’-联二噻吩
高分辨质谱理论值：458.0647，实测值：458.0649。
实施例19
化合物4,4’-二(4-磺酸基-苯乙烯基)-3,3’-联二噻吩
高分辨质谱理论值：529.9986，实测值：529.9988。
实施例20
化合物4,4’-二(4-羟基-苯乙烯基)-3,3’-联二噻吩
高分辨质谱理论值：402.0748，实测值：402.0746。
本发明中，5,5’-二(苯乙烯基)-3,3’-联二噻吩衍生物是一类新的化合物，还没有被报道过。
在氯仿溶液中，化合物的荧光最大发射波长在420-440nm之间，发出明亮的蓝紫色光。这些化合物的光谱响应带宽阔(在400-500nm均有光谱信号)，并且具有高摩尔消光系数，能够实现对光子的有效吸收。因此这些化合物可作为有机小分子光电材料，在有机染料、染料敏化太阳能电池、有机发光二极管、有机场效应晶体管和有机半导体材料领域应用。

Claims (5)

1.一种5,5’-二(苯乙烯基)-3,3’-联二噻吩衍生物，其特征在于，其具有通式Ⅰ所示的结构：
其中，R选自氢，甲基，溴甲基，甲氧基，苯甲氧基，氟，氯，溴，碘，氰基，硝基，氨基，苯基，叔丁基，三氟甲基，磺酸基，羧基，羟基，甲砜基或甲酸甲酯基中任意一种。
2.一种如权利要求1所述的5,5’-二(苯乙烯基)-3,3’-联二噻吩的衍生物的合成方法，其特征在于：通过5,5’-二醛基-3,3’-联二噻吩与芳基苄溴类wittig试剂反应制备得到5,5’-二(苯乙烯基)-3,3’-联二噻吩衍生物；其中：芳基苄溴类wittig试剂的结构式为
3.如权利要求2所述的合成方法，其特征在于，碱选自K2CO3、NaCO3、CH3COOK、NaOH、KOH、CH3CH2ONa、CH3COONa、DBU或n-BuLi中任意一种。
4.如权利要求2所述的合成方法，其特征在于，溶剂选自Et2O、THF、CHCl3或CH2Cl2中任意一种。
5.一种如权利要求1所述的5,5’-二(苯乙烯基)-3,3’-联二噻吩的衍生物在有机染料、染料敏化太阳能电池、有机发光二极管、有机场效应晶体管和有机半导体材料领域的应用。
CN201811279291.7A 2018-10-30 2018-10-30 5,5’-二(苯乙烯基)-3,3’-联二噻吩衍生物、合成方法及其应用 Pending CN109232520A (zh)

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