CN109265435A - 4,4’-二芳基-3,3’-联二噻吩衍生物、合成方法及其应用 - Google Patents
4,4’-二芳基-3,3’-联二噻吩衍生物、合成方法及其应用 Download PDFInfo
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Abstract
本发明公开了一种4,4’‑二芳基‑3,3’‑联二噻吩衍生物、合成方法及其应用。本发明的衍生物通过将4,4’‑二溴‑3,3’‑联二噻吩和芳基硼酸酯底物Ar‑B(OH)2发生Suzuki偶联反应得到;其中:所述Ar为苯基,取代的苯基、1‑萘基、2‑萘基或蒽基等。它们具有良好的光学性能,可作为有机小分子光电材料,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。
Description
技术领域
本发明属于有机合成技术领域,具体的说,涉及一种4,4’-二芳基-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。
Garnier等人利用有机小分子齐聚六噻吩(α-sexithiophene)(式-1,J.Am.Chem.Soc,2005,127:3997-4009.)作为有源层,利用蒽对齐聚噻吩进行封端也可以调节分子的能级结构,获得相对稳定的高迁移率有机半导体材料。
Sirringhous等人设计合成了S原子在不同侧的二聚并三噻吩(式-2,ppl.Phys.Lett,1997,71:3871-3873.),该化合物是一种空穴累积型(p-型)的有机半导体材料,具有独特的面面π堆积结构,较宽的HOMO-LUMO能隙,较高的开关比。
朱道本和罗臻等人研究了低聚噻吩酸类化合物(式-3,高等学校化学学报.2004,25:154-156.)对纳米二氧化钛的敏化效果的影响,通过其与N3染料的共敏化后,发现低聚噻吩酸类化合物可使染料的光谱吸收范围变宽,提高了染料敏化太阳能电池的性能。
Asil等设计合成出带有强吸电子基团的噻吩衍生物单体A,通过电化学聚合后得到类似于噻吩共聚物(式-4,J.Electroanal.Chem.,2008,618:87-93),可作为较好的电致变色器具。
发明内容
本发明的目的在于公开一种新的具有良好光电性能的4,4’-二芳基-3,3’-联二噻吩衍生物、合成方法及其应用。
本发明的技术方案具体介绍如下。
本发明提供一种2,2’-二芳基-3,3’-联二噻吩衍生物,其结构如式(Ⅰ)所示:
其中:Ar为取代的苯基、2-联苯、3-联苯、4-联苯、1-萘基、2-萘基或蒽基。优选的,所述取代的苯基为一个或者两个位置独立的被CH3,OCH3,NO2,NH2,F,Cl、Br或芳基取代的苯基。
本发明还提供一种上述4,4’-二芳基-3,3’-联二噻吩衍生物的合成方法,其通过将4,4’-二溴-3,3’-联二噻吩和芳基硼酸酯底物Ar-B(OH)2发生Suzuki偶联反应得到;其中:所述Ar为苯基,取代的苯基、1-萘基、2-萘基或蒽基。
优选的,Suzuki偶联反应中,通过对比K2CO3、CH3COOK、Cs2CO3、NaOH、CH3CH2ONa、和n-BuLi后,碱采用强度适中的K2CO3。
本发明进一步提供一种上述4,4’-二芳基-3,3’-联二噻吩衍生物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)4,4’-二芳基-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6的荧光谱图。
图2为实施例8的荧光谱图。
图3为实施例34的荧光谱图。
具体实施方式
本发明各实施例中用到的THF、Pd(PPh3)4、Ar-B(OH)2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。
Suzuki反应:100mL的烧瓶中依次加入4,4’-二溴-3,3’-联二噻吩(1.20mmol),Pd(PPh3)4(0.072mmol),芳基硼酸化合物(2.64mmol),碳酸钾(7.20mmol)和THF(32mL),回流至TLC检测原料反应完全。滴加少量盐酸淬灭反应,减压除去THF,乙酸乙酯(3×20mL)萃取,10%的碳酸氢钠溶液洗涤,无水硫酸钠干燥分液后的有机相,减压浓缩有机相,硅胶柱层析分离得到纯产品(展开剂为不同比例的乙酸乙酯和石油醚混合液)。化学方程式如下所示:
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不多于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。最后,保存相应的谱图和数据。
实施例1
化合物4,4’-二(1-萘基)-3,3’-联二噻吩。
高分辨质谱理论值:418.0801,实测值:418.0802。
实施例2
化合物4,4’-二[(4-甲氧基)-苯基]-3,3’-联二噻吩。
高分辨质谱理论值:378.0712,实测值:378.0714。
实施例3
化合物4,4’-二(3-联苯基)-3,3’-联二噻吩。
高分辨质谱理论值:470.1212,实测值:470.1215。
实施例4
化合物4,4’-二[(3-硝基)-苯基]-3,3’-联二噻吩。
高分辨质谱理论值:408.0222,实测值:408.0224。
实施例5
化合物4,4’-二[(3-氨基)-苯基]-3,3’-联二噻吩。
1H NMR(500MHz,DMSO,ppm)δ7.960(s,2H),5.925(t,J=8.0Hz,3H),5.143(d,J=5Hz,5H),5.075(d,J=7.5Hz,2H),4.006(s,4H)。
高分辨质谱理论值:348.0823,实测值:348.0825。
实施例6
化合物4,4’-二[(3-甲氧基)-苯基]-3,3’-联二噻吩。
1H NMR(500MHz,CDCl3,ppm)δ7.233(d,J=3Hz,2H),7.093(d,J=3Hz,2H),6.865(t,J=8.0Hz,2H),6.579-6.557(m,2H),6.281(d,J=8.0Hz,2H),6.179(s,2H),3.491(s,6H)。
13C NMR(125MHz,CDCl3,ppm)δ158.95,142.39,137.39,136.64,128.63,124.55,122.76,120.55,112.90,112.67,54.90.
高分辨质谱理论值:378.0712,实测值:378.0710。
图1为实施例6的荧光谱图。
荧光光谱最大发射波长:437nm。
荧光值:40400。
实施例7
化合物4,4’-二(4-溴-苯基)-3,3’-联二噻吩。
高分辨质谱理论值:473.8721,实测值:473.8724。
实施例8
化合物4,4’-二(4-联苯基)-3,3’-联二噻吩。
1H NMR(500MHz,CDCl3,ppm)δ7.460(d,J=7Hz,4H),7.369(t,J=7.5Hz,4H),7.275–7.247(m,4H),7.171(d,J=8.0Hz,4H),7.132(d,J=2.5Hz,2H),6.745(d,J=8.0Hz,4H)。
13C NMR(125MHz,CDCl3,ppm)δ142.00,140.99,139.05,136.52,135.28,128.75,128.35,127.14,126.90,126.37,124.76,122.92.
高分辨质谱理论值:470.1231,实测值:470.1230。
图2为实施例8的荧光谱图。
荧光光谱最大发射波长:438nm。
荧光值:39900。
实施例9
化合物4,4’-二[(2-甲氧基)-苯基]-3,3’-联二噻吩,高分辨质谱理论值:378.0712,实测值:378.0714。
实施例10
化合物4,4’-二[(2-甲基)-苯基]-3,3’-联二噻吩,高分辨质谱理论值:346.0805,实测值:346.0803。
实施例11
化合物4,4’-二[(3-甲氧基)-苯基]-3,3’-联二噻吩,高分辨质谱理论值:378.0713,实测值:378.0716。
实施例12
化合物4,4’-二[(4-甲基)-苯基]-3,3’-联二噻吩,高分辨质谱理论值:346.0805,实测值:346.0802。
实施例13
化合物4,4’-二[(4-硝基)-苯基]-3,3’-联二噻吩,高分辨质谱理论值:408.0222,实测值:408.0226。
实施例14
化合物4,4’-二[(2-硝基)-苯基]-3,3’-联二噻吩,高分辨质谱理论值:408.0222,实测值:408.0220。
实施例15
化合物4,4’-二[(2-氨基)-苯基]-3,3’-联二噻吩,高分辨质谱理论值:348.0801,实测值:348.0802。
实施例16
化合物4,4’-二[(4-氨基)-苯基]-3,3’-联二噻吩,高分辨质谱理论值:348.0801,实测值:348.0804。
实施例17
化合物4,4’-二(2-氟-苯基)-3,3’-联二噻吩,高分辨质谱理论值:354.0331,实测值:354.0334。
实施例18
化合物4,4’-二(3-氟-苯基)-3,3’-联二噻吩,高分辨质谱理论值:354.0331,实测值:3534。
实施例19
化合物4,4’-二(4-氟-苯基)-3,3’-联二噻吩,高分辨质谱理论值:354.0331,实测值:354.0335。
实施例20
化合物4,4’-二(2-氯-苯基)-3,3’-联二噻吩,高分辨质谱理论值:385.9821,实测值:385.9819。
实施例21
化合物4,4’-二(3-氯-苯基)-3,3’-联二噻吩,高分辨质谱理论值:385.9821,实测值:385.9820。
实施例22
化合物4,4’-二(4-氯-苯基)-3,3’-联二噻吩,高分辨质谱理论值:385.9821,实测值:385.9819。
实施例23
化合物4,4’-二(2-溴-苯基)-3,3’-联二噻吩,高分辨质谱理论值:473.8710,实测值:473.8713。
实施例24
化合物4,4’-二(3-溴-苯基)-3,3’-联二噻吩,高分辨质谱理论值:473.8710,实测值:473.8714。
实施例25
化合物4,4’-二(2-联苯基)-3,3’-联二噻吩,高分辨质谱理论值:470.1212,实测值:470.1211。
实施例26
化合物4,4’-二[(3-甲基)-苯基]-3,3’-联二噻吩,高分辨质谱理论值:346.0805,实测值:346.0808。
实施例27
化合物4,4’-二[(2,3,4,5,6-五氯)-苯基]-3,3’-联二噻吩,高分辨质谱理论值:657.6640,实测值:657.6638。
实施例28
化合物4,4’-二[(2,4,6-三溴)-苯基]-3,3’-联二噻吩,高分辨质谱理论值:785.5169,实测值:。
实施例29
化合物4,4’-二[(2,4,6-三氯)-苯基]-3,3’-联二噻吩,高分辨质谱理论值:521.8199,实测值:521.8197。
实施例30
化合物4,4’-二[(2,4,6-三氟)-苯基]-3,3’-联二噻吩,高分辨质谱理论值:425.9972,实测值:425.9971。
实施例31
化合物4,4’-二[(2,3,4,5,6-五氟)-苯基]-3,3’-联二噻吩,高分辨质谱理论值:497.9595,实测值:497.9598。
实施例32
化合物4,4’-二[(3,5-二溴)-苯基]-3,3’-联二噻吩,高分辨质谱理论值:629.7010,实测值:629.7012。
实施例33
化合物4,4’-二苯基-3,3’-联二噻吩,高分辨质谱理论值:318.0537,实测值:318.0539。
1H NMR(500MHz,CDCl3,ppm)δ7.162(d,J=3Hz,2H),7.071(d,J=3Hz,2H),7.005(d,J=8.0Hz,2H),6.958(t,J=7.5Hz,4H),6.697(d,J=7Hz,4H)。
13C NMR(125MHz,CDCl3,ppm)δ142.48,136.40,136.24,127.99,127.73,126.29,124.68,122.88.
荧光光谱最大发射波长:437nm。
荧光值:31200。
摩尔消光系数:17240M-1·cm-1。
实施例34
化合物4,4’-二[(N,N-二苯基苯胺)苯基]-3,3’-联二噻吩,高分辨质谱理论值:652.8740,实测值:652.8737。
1H NMR(500MHz,CDCl3,ppm)δ7.608(d,J=7.5Hz,3H),7.513(d,J=8.5Hz,3H),7.461(t,J=7.5Hz,3H),7.334-7.283(m,9H),7.175(d,J=8Hz,10H),7.076(t,J=7Hz,4H)。
13C NMR(125MHz,CDCl3,ppm)δ13C NMR(126MHz,Chloroform-d)δ147.72,147.21,140.68,135.17,129.30,128.75,127.79,126.82,126.68,124.44,123.94,122.94.
图3为实施例34的荧光谱图。
荧光光谱最大发射波长:532nm。
荧光值:412000。
摩尔消光系数:53260M-1·cm-1。
实施例35
化合物4,4’-二[(4-叔丁基)苯基]-3,3’-联二噻吩,高分辨质谱理论值:430.1789,实测值:430.1788。
实施例36
化合物4,4’-二[(N,N-二甲苯基苯胺)苯基]-3,3’-联二噻吩,高分辨质谱理论值:708.2633,实测值:708.2630。
实施例37
化合物4,4’-二[(N,N-二甲氧基苯基苯胺)苯基]-3,3’-联二噻吩,高分辨质谱理论值:772.2429,实测值:772.2430。
实施例38
化合物4,4’-二奈基-3,3’-联二噻吩,高分辨质谱理论值:418.0850,实测值:418.0851。
实施例39
化合物4,4’-二[(二吩噻嗪基)苯基]-3,3’-联二噻吩,高分辨质谱理论值:712.1135,实测值:712.1137。
本发明的化合物在氯仿溶液中呈现出蓝绿色;各化合物的荧光最大发射波长在415-550nm之间。这些化合物在室温或太阳光照射条件下放置长时间不变色。这些化合物光谱响应带宽阔(实施例34在400-700nm有光谱信号,而实施例6和8在380-550nm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,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。
Claims (5)
1.一种4,4’-二芳基-3,3’-联二噻吩衍生物,其特征在于,其结构如式(Ⅰ)所示:
其中:Ar为苯基、取代的苯基、1-萘基、2-萘基或蒽基。
2.根据权利要求1所述的4,4’-二芳基-3,3’-联二噻吩衍生物,其特征在于,所述取代的苯基为一个或者两个位置独立的被CH3,OCH3,NO2,NH2,F,Cl、Br或芳基取代的苯基。
3.一种如权利要求1或2所述的4,4’-二芳基-3,3’-联二噻吩衍生物的合成方法,其特征在于,其通过将4,4’-二溴-3,3’-联二噻吩和芳基硼酸酯底物Ar-B(OH)2发生Suzuki偶联反应得到;其中:所述Ar为苯基,取代的苯基、1-萘基、2-萘基或蒽基。
4.根据权利要求3所述的合成方法,其特征在于,碱为K2CO3。
5.一种如权利要求1所述的4,4’-二芳基-3,3’-联二噻吩衍生物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的应用。
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