CN108164546B - 吲哚啉-二噻吩并喹喔啉-二苯并[a，c]吩嗪染料及其在染料敏化太阳电池中的应用 - Google Patents
吲哚啉-二噻吩并喹喔啉-二苯并[a，c]吩嗪染料及其在染料敏化太阳电池中的应用 Download PDFInfo
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- indoline
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- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D495/14—Ortho-condensed systems
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- C09B17/00—Azine dyes
- C09B17/005—Dyes containing at least four ortho-condensed rings with at least two ring N-atoms in the system, e.g. fluoflavine, fluorubine, fluorindine
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G9/00—Electrolytic capacitors, rectifiers, detectors, switching devices, light-sensitive or temperature-sensitive devices; Processes of their manufacture
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Abstract
本发明公开了吲哚啉‑二噻吩并喹喔啉‑二苯并[a，c]吩嗪染料及其在染料敏化太阳电池中的应用。该染料为D‑A‑π‑A型纯有机染料，其中，以吲哚啉基团为电子供体，二噻吩并喹喔啉基团和噻吩基团为π桥，氰基乙酸基团为电子受体和锚固基团，同时引入二苯并[a，c]吩嗪基团作为电子辅助受体。本发明的染料分子中引入二苯并[a，c]吩嗪辅助电子受体，增加染料分子的共轭性和调节分子轨道能级，通过共轭大π桥二辛基二噻吩并喹喔啉的刚性平面促进分子内电子转移，并通过烷基链抑制染料的聚集，有效扩大光谱响应范围，延长了电子寿命，具有良好的吸光能力，基于该染料的染料敏化太阳电池能获得到大的光电流，从而取得较高的光电转换效率。
Description
技术领域
本发明涉及有机染料技术领域，具体涉及染料敏化太阳电池用的敏化染料及其应用。
背景技术
染料敏化太阳能电池(DSSCs)是一种新型的将太阳能转化为电能的装置。这类电池因为其制备简单方便而且有着较高的能量转换效率使之在室内或商业上的应用成为可能，因此引起人们极大的关注。其优点在于它廉价的成本和简单的制备工艺。对于高性能染料敏化太阳能电池来说，敏化染料的结构对电池的光电转换效率起着决定性作用。目前，有着最高光电转换效率的是多吡啶钌配合物染料，但是此类染料需要用到稀有金属钌而且分离提纯比较困难。而纯有机染料因其合成简单、分子结构易于设计与调节、摩尔消光系数高等优点，近来得到了广泛的开发与应用。
相对于传统的D-π-A型染料，D-A-π-A型染料由于辅助受体的引入，分子内电子转移更加容易。吩嗪类结构是一类良好的电子受体材料，其结构具有良好的平面性，有利于分子内电荷转移，而且容易合成与修饰，通过与苯环连接合成二苯并[a，c]吩嗪调节其吸电子能力、扩大染料的共轭从而有效地拓宽染料分子的吸光范围。目前还没有报道以吲哚啉为电子供体，以二苯并[a，c]吩嗪为辅助受体的喹喔啉染料。本发明设计并合成一类以吲哚啉为电子给体，二苯并[a，c]吩嗪为辅助受体，二噻吩并喹喔啉和噻吩为π桥，氰基乙酸为电子受体和锚固基团的纯有机染料。该染料具有结构简单，易于合成，光电转换性能良好等优点。
发明内容
本发明的目的在于针对现有技术的不足，提供了一种吲哚啉-二噻吩并喹喔啉-二苯并[a，c]吩嗪染料。该染料为不含金属的D-A-π-A型纯有机染料，其中，以吲哚啉基团为电子供体，二噻吩并喹喔啉基团和噻吩基团为π桥，氰基乙酸基团为电子受体和锚固基团，同时引入二苯并[a，c]吩嗪基团作为电子辅助受体。
本发明的吲哚啉-二噻吩并喹喔啉-二苯并[a，c]吩嗪染料合成工艺简单，原料廉价易得，能进行规模化生产。
本发明的另一目的还在于提供所述的一种吲哚啉-二噻吩并喹喔啉-二苯并[a，c]吩嗪染料在染料敏化太阳电池中的应用。该吲哚啉－二噻吩并喹喔啉-二苯并[a，c]吩嗪染料作为敏化剂应用于染料敏化太阳电池中，使得染料敏化太阳电池具有良好的光电性能。
本发明的目的通过如下技术方案实现。
一种吲哚啉-二噻吩并喹喔啉-二苯并[a，c]吩嗪染料，化学结构式如下所示：
式中，R1和R2均独立选自C1～C20的直链烷基、C1～C20的支链烷基或C1～C20的烷氧基；X为O或S；
其中，氰基乙酸基团为电子受体和锚固基团。
上述所述的一种吲哚啉-二噻吩并喹喔啉-二苯并[a，c]吩嗪染料在染料敏化太阳电池中的应用，将所述吲哚啉-二噻吩并喹喔啉-二苯并[a，c]吩嗪染料作为敏化剂应用于染料敏化太阳电池中，具体为：将负载纳米二氧化钛的导电玻璃基底浸泡在吲哚啉-二噻吩并喹喔啉-二苯并[a，c]吩嗪染料配制的染浴溶液中，吲哚啉-二噻吩并喹喔啉-二苯并[a，c]吩嗪染料通过锚固基团吸附在纳米二氧化钛表面，制备成染料敏化太阳电池的工作电极。
进一步地，所述染浴溶液的溶剂包括四氢呋喃。
进一步地，所述染浴溶液的浓度为1～5×10-4mol·L-1。
进一步地，所述浸泡是在阴暗避光环境中浸泡10～24小时。
与现有技术相比，本发明具有如下优点和有益效果：
本发明的吲哚啉-二噻吩并喹喔啉-二苯并[a，c]吩嗪染料分子中引入二苯并[a，c]吩嗪辅助电子受体，增加染料分子的共轭性和调节分子轨道能级，通过共轭大π桥二辛基二噻吩并喹喔啉的刚性平面促进分子内电子转移，并通过烷基链抑制染料的聚集，有效扩大光谱响应范围，延长了电子寿命，具有良好的吸光能力，基于该染料的染料敏化太阳电池能获得到大的光电流，从而取得较高的光电转换效率。
附图说明
图1为实施例1中合成的染料IQ在四氢呋喃溶液中的紫外/可见吸收谱图；
图2为实施例1中合成的染料IQ作为敏化剂制作的染料敏化太阳电池的J-V曲线图。
具体实施方式
以下结合具体实施例及附图对本发明的技术方案作进一步详细的描述，但本发明的保护范围及实施方式不限于此。
实施例1
吲哚啉-二噻吩并喹喔啉-二苯并[a，c]吩嗪染料IQ(R1＝C8H17(正辛基)，R2＝C8H17(正辛基)，即R1和R2同为含有8个碳原子的直链烷基，X为硫原子)的合成，合成路线如下所示：
具体合成过程包括如下步骤：
(1)化合物2的合成
在氮气气氛中，将4.6g(10mmol)化合物1溶解到25mL四氢呋喃(THF)中，然后降温到0℃，往反应液中加入N-溴代琥珀酰亚胺(4.4g，25mmol)，自然升至常温，反应12h，加入30mL水淬灭反应，用二氯甲烷萃取；有机相用水洗涤两次，干燥，浓缩，粗产物用10mL正己烷重结晶，得到5g白色固体，即化合物2，收率80％。熔点100.3-101.6℃。1H NMR(400MHz，Chloroform-d)δ8.05(s，2H)，2.95(t，J＝7.8Hz，4H)，1.86(m，J＝7.5Hz，4H)，1.55-1.25(m，20H)，0.90(t，J＝6.6Hz，6H).
(2)化合物3的合成
在50mL两口反应瓶中加入化合物2(880mg，1.41mmol)、5-醛基-2-噻吩硼酸(219mg，1.41mmol)、四(三苯基膦)钯(160mg，0.14mmol)、2M的碳酸钾水溶液(1.5mL)和重蒸的30mL的四氢呋喃，用真空泵抽出装置中的空气，并充入氩气；油浴升温到80℃反应20小时；反应结束后，降至室温，反应液倒入水中，用3×50mL二氯甲烷萃取，合并有机相并用饱和食盐水洗涤后，用无水硫酸钠干燥，旋蒸除去二氯甲烷，残余物以石油醚(bp 60-90℃)和乙酸乙酯(v/v＝10∶1)为洗脱剂经硅胶柱层析色谱分离纯化，真空干燥后，得黄色固体(281mg，0.43mmol)，即化合物3，产率为30.5％，熔点149-151℃。1H NMR(400MHz，Chloroform-d)δ9.90(s，1H)，8.38(s，1H)，8.19(s，1H)，7.70(d，J＝3.9Hz，1H)，7.38(d，J＝4.0Hz，1H)，3.02(q，J＝7.4Hz，4H)，1.90(m，4H)，1.54-1.23(m，20H)，0.90(m，6H).
(3)化合物5的合成
在50mL的两口瓶中，加入化合物4(1.34g，2mmol)、4-对甲苯基环戊烷吲哚啉硼酸酯(500mg，1.33mmol)、四(三苯基膦)钯(153mg，0.13mmol)、2M的碳酸钾水溶液(2mL)和重蒸的20mL的四氢呋喃，用真空泵抽出装置中的空气，并充入氩气；油浴升温到80℃，反应24小时；反应结束后，将反应液倒入水中，用3×50mL二氯甲烷萃取，合并有机相并用饱和食盐水洗涤后，用无水硫酸钠干燥，旋蒸除去二氯甲烷，残余物以石油醚(bp 60-90℃)和乙酸乙酯(v/v＝50∶1)为洗脱剂经硅胶柱层析色谱分离纯化，真空干燥后，得红色固体(863mg，1mmol)，即化合物5，产率为75％。1H NMR(400MHz，Chloroform-d)δ9.52(d，J＝8.0Hz，1H)，9.19(d，J＝8.0Hz，1H)，8.55(d，J＝8.0Hz，2H)，8.19(d，J＝7.8Hz，1H)，7.86-7.71(m，5H)，7.66(t，J＝7.5Hz，1H)，7.60(d，J＝8.3Hz，1H)，7.31(d，J＝8.2Hz，2H)，7.22(d，J＝8.1Hz，2H)，7.12(d，J＝8.2Hz，1H)，4.96-4.88(m，1H)，3.98(q，J＝6.3Hz，1H)，2.37(s，3H)，2.20-1.70(m，6H).
(4)化合物6的合成
在50mL两口反应瓶中，加入化合物5(300mg，0.35mmol)、联频哪醇硼酸酯(353mg1.36mmol)、醋酸钾(136mg，1.36mmol)、1，1′-双二苯基膦二茂铁二氯化钯(25mg，0.03mmol)和25mL的重蒸1，4-二氧六环，用真空泵抽出装置中的空气，并充入氩气；油浴升温至100℃，反应24小时；反应结束后，降至室温，将反应液倒入水中，用3×50mL二氯甲烷萃取，合并有机相并用饱和食盐水洗涤后，用无水硫酸钠干燥，旋蒸除去二氯甲烷，残余物以二氯甲烷和乙酸乙酯(v/v＝4∶1)为洗脱剂经硅胶柱层析色谱分离后，得红色固体粗产物284mg；
再将得到的粗产物和化合物3(223mg 0.34mmol)加入50mL的两口瓶中，再加入20mL四氢呋喃、四(三苯基膦)钯(34mg，0.03mmol)和2M的碳酸钾水溶液(1mL)，用真空泵抽出装置中的空气，并充入氩气；油浴升温到80℃反应24小时，反应结束后，降至室温，反应液倒入水中，用3×50mL二氯甲烷萃取，合并有机相并用饱和食盐水洗涤后，用无水硫酸钠干燥，旋蒸除去二氯甲烷，残余物以石油醚(bp60-90℃)和乙酸乙酯(v/v＝10∶1)为洗脱剂经硅胶柱层析色谱分离纯化，真空干燥后，得红色固体(223mg，0.16mmol)，即化合物6，产率为47％，熔点187-189℃。1H NMR(400MHz，Chloroform-d)δ9.66(s，1H)，8.89-8.82(m，1H)，8.59(d，J＝7.7Hz，1H)，7.99(s，1H)，7.93(dd，J＝12.3，7.4Hz，2H)，7.62(s，1H)，7.57(d，J＝6.2Hz，2H)，7.39-7.30(m，4H)，7.17-7.31(m，7H)，7.02(d，J＝8.0Hz，1H)，6.74(d，J＝3.7Hz，1H)，4.85-4.83(m，1H)，3.86(td，J＝8.3，3.4Hz，1H)，2.56(td，J＝9.5，6.2Hz，4H)，2.41(s，3H)，2.16-1.84(m，4H)，1.71-1.69(m，6H)，1.35-1.33(m，20H)，0.93(q，J＝7.0Hz，6H).
(5)染料IQ的合成
在50mL两口反应瓶中，加入化合物6(223mg，0.16mmol)、氰基乙酸叔丁酯(66.00mg，0.48mmol)、醋酸铵(36.00mg，0.48mmol)、醋酸(2mL)和25mL的甲苯，用真空泵抽出装置中的空气，并充入氩气；油浴升温至130℃，反应液回流反应5小时；反应结束后，降至室温，将反应液倒入水中，用3×50mL二氯甲烷萃取，合并有机相并用饱和食盐水洗涤后，用无水硫酸钠干燥，旋蒸除去二氯甲烷，残余物以石油醚(bp60-90℃)和乙酸乙酯(v/v＝20∶1)为洗脱剂经硅胶柱层析色谱分离纯化，真空干燥后，得到的红色固体直接加入25mL的单口瓶中，再加入8mL三氟乙酸，于常温下搅拌4h；反应结束后，将反应液倒入100mL的去离子水中，待固体析出，过滤收集固体，并用去离子水反复洗涤直至洗涤产生的液体的pH为中性，干燥，得黑色固体染料(189mg，0.13mmol)，即IQ染料，产率为83％，熔点为247-249℃。1HNMR(400MHz，THF-d8)δ9.48(d，J＝7.9Hz，1H)，8.99(d，J＝8.0Hz，1H)，8.70(s，1H)，8.46(t，J＝7.6Hz，2H)，8.31(s，1H)，8.20(d，J＝8.0Hz，1H)，8.13(s，1H)，7.85(s，1H)，7.81-7.71(m，3H)，7.66-7.64(m，2H)，7.55(t，J＝7.9Hz，2H)，7.35(t，J＝8.4Hz，3H)，7.24(d，J＝8.1Hz，2H)，7.12(d，J＝8.2Hz，1H)，5.01-4.98(m，1H)，4.05-4.02(m，1H)，2.94-2.91(m，4H)，2.40(s，3H)，2.30-1.85(m，8H)，1.60-1.30(m，22H)，0.96-0.93(m，6H).
实施例2
对实施例1合成的染料IQ进行紫外-可见吸收光谱测试，测试条件如下：
溶剂：四氢呋喃；
浓度：2×10-5M；
温度：室温；
仪器：Shimadzu UV-2450紫外可见分光光度计。
测试得到的紫外-可见吸收光谱图如图1所示，从图1中可以看出，在四氢呋喃溶液中，染料IQ表现为两个吸收峰，一个是π-π*跃迁的吸收峰，另一个是分子内电荷转移(ICT)的吸收峰，染料的摩尔消光系数较高，吸收范围宽，在400-550nm的范围内都超过了24000M- 1cm-1，这表明染料IQ具有良好的光捕获能力。
实施例3
染料敏化太阳电池的制备
将实施例1制备的染料IQ作为敏化剂用于染料敏化太阳电池中，制备基于染料IQ敏化剂的染料敏化太阳电池。
染料敏化太阳电池主要由导电玻璃基质(掺F的SnO2透明导电玻璃，即FTO)、光阳极、敏化剂、电解质溶液和铂对电极(也称光阴极，镀铂的导电玻璃)五大组成部分；其中，光阳极的基板导电玻璃面覆盖有纳米多孔TiO2薄膜，用以吸附染料；对电极的基板镀有Pt催化剂；光阳极和光阴极相对间隔设置，纳米多孔TiO2薄膜周边用密封材料密封形成密闭的腔体，腔体内填充有电解质溶液和敏化剂(即吲哚啉-二噻吩并喹喔啉-二苯并[a，c]吩嗪染料IQ)。
染料敏化太阳电池的具体制备过程包括如下步骤：
(1)透明导电玻璃基质(掺F的SnO2涂层，即FTO)的预处理：将裁好的FTO(2×5cm)用去离子水冲洗，再置于KOH的饱和乙醇溶液中浸泡24h，依次用去离子水50mL、丙酮30mL、去离子水50mL、乙醇30mL和去离子水50mL在超声下分别清洗30分钟，干燥后保存，待用；
(2)光阳极的制备：室温下，将10mL Ti(OBu)2和20mL乙醇的混合液剧烈搅拌下加入18mL乙酸和50mL去离子水并继续搅拌1h，再移入内衬特氟隆(聚四氟乙烯)的高压釜于230℃处理12h后，自然冷却至室温，过滤，用去离子水100mL、乙醇80mL依次洗涤，50℃下于烘箱中烘6h后，得到TiO2纳晶颗粒；
向制备的1.0g TiO2纳晶颗粒中，加入8.0mL乙醇、0.2mL乙酸、3.0g松油醇以及0.5g乙基纤维素后，充分研磨40min，得到泥浆状物质，经超声15min后得到白色粘性TiO2纳晶浆料；
将处理好的导电玻璃导电面朝上，将丝网板置于玻璃上方，控制1cm的网距，将制备好的TiO2纳晶浆料置于丝网上进行印刷，控制TiO2膜的厚度为17μm(面积为4×4mm)，得到负载纳米二氧化钛的导电玻璃基底；
将制备的负载纳米二氧化钛的导电玻璃基底放入烘箱，于125℃干燥5分钟，再放于马弗炉中，于325℃烘焙5min，再于375℃烘焙5min，再于450℃烘焙15min，最后于500℃烘焙15min，以充分除去膜上的有机物质，然后浸于0.2M的TiCl4水溶液中处理半小时；处理结束后，用去离子水反复冲洗干净，然后置于马弗炉中，升温至500℃再次烘焙30min，冷却至室温后，得到光阳极，置于密封袋并存于干燥器中备用；
(3)染料溶液的配制：将实施例1制备的染料IQ溶于四氢呋喃溶液中，配制成2×10-4mol·L-1染料溶液；
(4)电解质溶液的配制：用乙腈配制的含有0.6M 1-甲基-3-丙基碘化咪唑嗡、0.1M硫氰酸胍、0.03MI2和0.5M对叔丁基吡啶的溶液；
(5)光阳极的敏化：将步骤(2)制备的光阳极浸泡于步骤(3)配制的染料溶液中，在阴暗避光环境中染浴16小时后，取出，并用乙醇冲洗表面除去残留或物理吸附于膜表面的染料，吹干后保存于干燥避光环境以待封装，备用；
(6)用打孔器将胶带制成合适的内孔塑料，即绝缘薄膜，将此绝缘薄膜置于完成敏化的光阳极，使光阳极恰好处于绝缘薄膜内孔里；向TiO2膜表面滴加1～2滴电解质溶液，并在光阳极上盖制备的铂对电极，两边用夹子固定即形成待测的开放性敏化染料太阳电池。
染料敏化太阳电池性能测试：
从制备的染料敏化太阳电池的光阳极和光阴极分别引出导线，接到电池性能测试装置上，电池的工作面积为0.16cm2，用太阳光模拟器模拟太阳光，将光强度调节至100mW/cm2，测试基于染料IQ敏化的染料敏化太阳电池的J-V曲线。
所测得的J-V曲线图如图2所示，数据汇总于表1。
表1染料IQ用于染料敏化太阳电池的性能数据
从图2和表1的数据可以看出，染料IQ敏化的染料敏化太阳电池展现出较高的光电转换效率，拥有较高的短路电流和开路电压，这是由于这种D-A-π-A型染料具有较好的光捕获能力，电子注入二氧化钛效率高，电子不易复合。
上述实施例为本发明较佳的实施方式，但本发明的实施方式并不受上述实施例的限制，其它的任何未背离本发明的精神实质与原理下所作的改变、修饰、替代、组合、简化，均应为等效的置换方式，都包含在本发明的保护范围之内。
Claims (4)
1.一种吲哚啉-二噻吩并喹喔啉-二苯并[a，c]吩嗪染料，其特征在于，化学结构式如下所示：
2.权利要求1所述的一种吲哚啉-二噻吩并喹喔啉-二苯并[a，c]吩嗪染料在染料敏化太阳电池中的应用，其特征在于，将所述吲哚啉-二噻吩并喹喔啉-二苯并[a，c]吩嗪染料作为敏化剂应用于染料敏化太阳电池中，具体为：将负载纳米二氧化钛的导电玻璃基底浸泡在吲哚啉-二噻吩并喹喔啉-二苯并[a，c]吩嗪染料配制的染浴溶液中，吲哚啉-二噻吩并喹喔啉-二苯并[a，c]吩嗪染料通过锚固基团吸附在纳米二氧化钛表面，制备成染料敏化太阳电池的工作电极。
3.根据权利要求2所述的应用，其特征在于，所述染浴溶液的溶剂包括四氢呋喃；所述染浴溶液的浓度为1～5×10-4mol·L-1。
4.根据权利要求2所述的应用，其特征在于，所述浸泡是在阴暗避光环境中浸泡10～24小时。
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