CN102212274A - 一种三苯胺-苯基类有机染料及其应用 - Google Patents
一种三苯胺-苯基类有机染料及其应用 Download PDFInfo
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Abstract
Description
【技术领域】
本发明涉及染料敏化太阳能电池,特别涉及一种三苯胺-苯基类有机染料及其应用。
【背景技术】
在能源危机和环境污染的背景下,太阳能作为一种清洁可再生能源正逐步走入人类生活。其中,太阳能电池是利用太阳能的主要技术之一。染料敏化太阳能电池(O’Regan,B.;M.Nature 1991,353,737.)自问世以来,便以其高效、低成本、低能耗、环境友好等优点,显示出强大的商业应用前景。
目前,以Ru基多吡啶配合物作为光敏化剂,染料敏化太阳能电池的光电转换效率已经达到10%以上(Nazeeruddin,M.K.et al,J.Am.Chem.Soc.,2001,123,1613)。然而,这类光敏化剂使用贵金属,提纯复杂,成本较高。因此合成用于可替代Ru基多吡啶配合物的高效有机染料光敏剂成为该领域的研究热点。
近年来,三苯胺类光敏剂在染料敏化太阳能电池中的应用展现出良好的前景。本发明要解决的技术问题是,设计并合成一种适用于染料敏化太阳能电池的高效三苯胺-苯基类有机染料。
【发明内容】
本发明的目的是针对上述存在问题,提供一种三苯胺-苯基类有机染料及其在染料敏化太阳能电池中的应用。
本发明的技术方案:
一种三苯胺-苯基类有机染料,其结构通式为:
式I中:R1为C1~C12烷氧基,
Ar为六元芳环基或烷氧基取代六元芳环基,其结构式为II、III或IV:
式III、IV中:R2为C1~C12烷基。
一种所述三苯胺-苯基类有机染料的制备方法,采用二芳醛、叔丁醇钾、烷氧基取代三苯胺苄基三苯基膦盐作为原料,依次经魏悌息反应和缩合反应得到目标产物,其合成路线如下所示:
具体步骤如下:
1)烷氧基取代三苯胺苄基三苯基膦盐与二芳醛通过魏悌息反应得到烷氧基取代三苯胺苄基芳醛VI;
2)将烷氧基取代三苯胺苄基芳醛VI,醋酸铵和氰基乙酸置于冰乙酸中,回流条件下反应4小时,冷却后将反应液倒入冰水中,过滤得到固体粗产品,粗产品经柱层析分离得到烷氧基取代三苯胺苄基芳基酸VII。
一种所述三苯胺-苯基类有机染料的应用,作为染料敏化太阳能电池的光敏化剂,所述染料敏化太阳能电池包括导电玻璃、二氧化钛膜、光敏化剂、电解质和铂层,所述电解质的配方为在乙腈溶剂中,加入0.6M的1,2-二甲基-3-丙基咪唑碘、0.1M的碘化锂、0.05M的碘和0.5M叔丁基吡啶。
本发明的优点是:本发明提供的三苯胺-苯基类有机染料,是一种以烷氧基三苯胺作为有机染料的给电子单元、以苯基衍生物作为有机染料共轭桥的结构新颖的三苯胺-苯基类有机染料,其制备方法简单、便于操作、易于实施。该三苯胺-苯基类有机染料作为染料敏化太阳能电池中的光敏化剂,具有良好的光电转换性能。
【附图说明】
图1为实施例1-3制备的三苯胺-苯基类有机染料溶解于二氯甲烷中的紫外可见吸收光谱。
图2为实施例4制作的染料敏化太阳能电池结构示意图,图中:1.导电玻璃、2..二氧化钛膜、3.光敏化剂、4.电解质、5.铂层。
图3为实施例1-3制备的三苯胺-苯基类有机染料作为敏化剂的染料敏化太阳能电池的J-V曲线。
【具体实施方式】
下面通过实施例对本发明作进一步阐述,其目的在于更好地理解本发明的内容。因此,所举之例不限制本发明的保护范围。
实施例1:
制备三苯胺-苯基类有机染料3,其合成路线为:
具体步骤如下:
1)三苯胺烯苯甲醛2的合成
在100mL的三口瓶中,加入1.16g烷氧基取代三苯胺苄基三苯基膦盐1,30mL四氢呋喃。在零度下缓慢滴加0.162g叔丁醇钾的四氢呋喃溶液;混合物在零度下反应半小时后,加入0.194g对苯二甲醛,在氮气保护下升到室温反应过夜。加水淬灭反应,用二氯甲烷萃取,分液,用无水硫酸镁干燥有机相。减压蒸馏除掉溶剂,经柱层析(淋洗剂:石油醚/乙酸乙酯=10/1)分离得到0.167g三苯胺烯苯甲醛2,产率20%。
1H NMR(DMSO,400MHz):δ0.91(t,6H),1.26-1.31(m,8H),1.35-1.39(m,4H),1.59-1.69(m,4H),3.89(t,J=5.60Hz,4H),6.73(d,J=8.56Hz,2H),6.87(d,J=8.56Hz,4H),6.99(d,J=8.64Hz,4H),7.11(d,J=16.32Hz,1H),7.37(d,J=16.36Hz,1H),7.43(d,J=8.40Hz,2H),7.73(d,J=8.80Hz,2H),7.83(d,J=16.40Hz,2H),9.93(s,1H).13C NMR(DMSO,400MHz):δ13.98,14.34,19.12,22.36,22.54,25.50,25.68,29.19,29.48,30.48,31.48,31.76,39.39,65.46,68.08,115.90,119.04,124.48,126.90,127.43,128.42,129.11,130.45,131.92,132.19,132.29,134.96,139.90,144.21,149.15,155.97,167.40,192.54.HRMS(ESI)calcd for C39H45NO3[M+H]+:575.3399;Found:575.3382.
2)三苯胺-苯基类有机染料3的合成
在100mL圆底烧瓶中加入1g三苯胺烯苯甲醛2,0.167g氰基乙酸,10mL氰基乙酸,5mL氯仿,200uL哌啶,加热回流反应4小时。加水淬灭反应,用二氯甲烷萃取,分液,用无水硫酸镁干燥有机相。粗产品经柱层析(淋洗剂:二氯甲烷/甲醇=10/1)分离制得0.714g三苯胺-苯基类有机染料3,产率64%。
1H NMR(DMSO,400MHz):δ0.89(t,6H),1.28-1.32(m,8H),1.37-1.43(m,4H),1.66-1.73(m,4H),3.95(t,J=6.44Hz,4H),6.75(d,J=8.68Hz,2H),6.92(d,J=8.84Hz,4H),7.03(d,J=8.84Hz,4H),7.09(d,J=16.32Hz,1H),7.31(d,J=16.28Hz,1H),7.45(d,J=8.68Hz,2H),7.65(d,J=8.32Hz,2H),7.87(d,J=8.36Hz,2H),7.89(s,1H).13C NMR(DMSO,400MHz):δ14.38,22.54,25.68,29.17,31.47,39.37,55.39,68.09,115.95,119.26,120.05,124.96,126.84,127.38,128.20,128.84,130.25,130.60,132.28,140.03,140.42,146.98,148.86,155.89,163.55.HRMS(ESI)calcd for C42H46N2O4[M+H]+:642.3458.Found:642.3453
所制备的三苯胺-苯基类有机染料溶解于二氯甲烷中的紫外可见吸收光谱如图1所示。
实施例2:
制备三苯胺-苯基类有机染料5,其合成路线为:
具体步骤如下:
1)三苯胺烯2,5-二丙氧基苯甲醛4的合成
在100mL的三口瓶中,加入1.16g烷氧基取代三苯胺苄基三苯基膦盐1,30mL四氢呋喃。在零度下缓慢滴加0.162g叔丁醇钾的四氢呋喃溶液;混合物在零度下反应半小时后,加入0.362g 2,5-二丙氧基对苯二甲醛,在氮气保护下升到室温反应过夜。加水淬灭反应,用二氯甲烷萃取,分液,用无水硫酸镁干燥有机相。减压蒸馏除掉溶剂,经柱层析(淋洗剂:石油醚/二氯甲烷=5/1)分离得到0.151g三苯胺烯苯甲醛2,产率15%。
1H NMR(DMSO,400MHz):δ0.85-0.92(m,6H),0.98-1.03(m,6H),1.27-1.30(m,8H),1.34-1.41(m,4H),1.61-1.67(m,4H),1.75-1.79(m,4H),3.89-3.97(m,6H),4.13(t,J=6.32Hz,2H),6.75(d,J=8.52Hz,2H),6.91(d,J=8.68Hz,4H),7.03(d,J=8.64Hz,4H),7.18(s,1H),7.25(d,J=16.44Hz,1H),7.39(d,J=8.56Hz,2H),7.44(s,1H),7.47(d,J=16.16Hz,1H),10.31(s,1H).13C NMR(DMSO,400MHz):δ10.94,11.01,13.79,13.99,14.35,14.54,19.11,21.21,22.34,22.54,22.56,25.67,26.80,29.17,30.47,30.87,31.47,39.37,40.62,60.20,65.47,68.08,70.48,70.81,110.11,111.22,115.94,119.03,119.10,123.42,127.09,127.52,128.23,128.84,129.12,131.96,132.17,133.10,135.07,139.88,149.15,150.24,151.94,153.45,156.01,156.33,164.96,167.41,188.36.HRMS(ESI)calcd for C45H57NO5[M+H]+:691.4237.Found:691.4241.
2)三苯胺-苯基类有机染料5的合成
在100mL圆底烧瓶中加入1g三苯胺烯2,5-二丙氧基苯甲醛4,0.190g氰基乙酸,10mL氰基乙酸,5mL氯仿,200uL哌啶,加热回流反应7小时。加水淬灭反应,用二氯甲烷萃取,分液,用无水硫酸镁干燥有机相。粗产品经柱层析(淋洗剂:二氯甲烷/甲醇=12/1)分离制得0.602g三苯胺-苯基类有机染料5,产率55%。
1H NMR(DMSO,400MHz):δ0.84-0.87(m,6H),0.98-1.01(m,6H),1.20-1.28(m,8H),1.35-1.37(m,4H),1.61-1.68(m,4H),1.74-1.80(m,4H),3.87-3.94(m,6H),4.08(t,J=6.32Hz,2H),6.73(d,J=8.40Hz,2H),6.88(d,J=8.72Hz,4H),7.00(d,J=8.72Hz,4H),7.15(d,1H),7.25(d,J=16.36Hz,1H),7.36(s,1H),7.38(d,J=8.45Hz,2H),7.4(d,J=16.40Hz,1H),8.51(s,1H).13C NMR(DMSO,400MHz):δ13.99,14.34,19.11,19.32,22.50,22.54,22.57,22.86,23.71,24.96,25.68,28.83,29.11,29.18,29.50,30.28,30.48,30.88,31.47,31.76,34.82,38.56,39.38,40.63,53.04,65.46,67.85,68.09,68.15,70.56,70.86,110.31,111.72,115.91,116.17,118.15,119.07,119.19,119.80,125.35,127.47,128.20,128.68,128.94,129.10,131.89,131.99,132.08,132.58,133.14,133.56,138.17,139.89,145.92,149.09,149.84,153.43,155.99,157.18,164.49.HRMS(ESI)calcd for C48H58N2O6[M+H]+:758.4295.Found:758.4297.
所制备的三苯胺-苯基类有机染料溶解于二氯甲烷中的紫外可见吸收光谱如图1所示。
实施例3:
制备三苯胺-苯基类有机染料7,其合成路线为:
具体步骤如下:
1)三苯胺烯2,3;4,5-二烷氧基苯甲醛6的合成
在100mL的三口瓶中,加入1.16g烷氧基取代三苯胺苄基三苯基膦盐1,30mL四氢呋喃。在零度下缓慢滴加0.161g叔丁醇钾的四氢呋喃溶液;混合物在零度下反应半小时后,加入0.403g 2,3;4,5-二烷氧基对苯二甲醛,在氮气保护下升到室温反应过夜。加水淬灭反应,用二氯甲烷萃取,分液,用无水硫酸镁干燥有机相。减压蒸馏除掉溶剂,经柱层析(淋洗剂:石油醚/乙酸乙酯=10/1)分离得到0.365g三苯胺烯苯甲醛6,产率35%。
1H NMR(CDCl3,400MHz):δ0.92(t,6H),1.34-1.36(m,8H),1.45-1.48(m,4H),1.75-1.80(m,16H),3.95(t,J=6.48Hz,4H),6.84(d,J=16.4Hz,1H),6.84(d,J=8.92Hz,4H),6.89(d,J=8.44Hz,2H),7.06(d,J=8.68Hz,4H),7.35(d,J=8.52Hz,2H),7.48(d,J=16.4Hz,1H),10.04(s,1H).13C NMR(CDCl3,100MHz):δ14.04,22.62,25.77,25.93,29.33,30.92,31.62,68.29,76.71,104.57,112.78,114.31,115.30,119.84,120.08,126.83,127.78,129.01,135.86,138.23,140.26,140.71,149.15,155.76,185.07.HRMS(ESI)calcd for C45H53NO7[M+H]+:719.3822.Found:719.3825.
所制备的三苯胺-苯基类有机染料溶解于二氯甲烷中的紫外可见吸收光谱如图1所示。
2)三苯胺-苯基类有机染料7的合成
在100mL圆底烧瓶中加入1g三苯胺烯2,3;4,5-二烷氧基苯甲醛6,0.210g氰基乙酸,10mL氰基乙酸,5mL氯仿,200uL哌啶,加热回流反应5小时。加水淬灭反应,用二氯甲烷萃取,分液,用无水硫酸镁干燥有机相。粗产品经柱层析(淋洗剂:二氯甲烷/甲醇=10/1)分离制得0.754g三苯胺-苯基类有机染料7,产率69%。
1H NMR(CDCl3,400MHz):δ0.92(t,6H),1.34-1.36(m,7H),1.45-1.48(m,4H),1.75-1.80(m,16H),2.17(s,2H),3.95(t,J=6.48Hz,4H),6.72(d,J=8.20Hz,2H),6.75(d,J=16.08Hz,1H),6.88(d,J=8.84Hz,4H),7.00(d,J=8.72Hz,4H),7.31(d,J=16.04Hz,1H),7.33(d,J=8.84Hz,2H),7.79(s,1H).13C NMR(CDCl3,100MHz):δ14.32,22.50,25.59,25.65,26.02,29.17,29.43,31.45,39.45,39.66,39.87,67.48,68.15,116.00,119.14,119.80,127.48,128.07,139.98,156.02.HRMS(ESI)calcd for C48H54N2O8[M+H]+:786.3880.Found:786.3883.
实施例4:
以三苯胺-苯基类有机染料5作为光敏化剂制作染料敏化太阳能电池,该电池装置的结构图见图2,图2中:1.导电玻璃、2.二氧化钛膜、3.光敏化剂、4.电解质、5.铂层。该电池有效光照面积为0.16cm2;测试光源AM1.5solar simulator-Oriel 91160-1000(300W);数据采集Keithley 2400数字源表。测量上述染料敏化太阳能电池器件的光电转换性能,测试结果表明,该电池具有良好的光电转换性能,光电转换效率达到7%以上。
将制备好的二氧化钛电极在80℃下加热10分钟,然后浸泡到三苯胺-苯基类有机染料5配制的3×10-4M的乙醇溶液中。24小时后取出,用无水乙醇冲洗电极表面,吹干。电解液配方为:在乙腈溶剂中,加入0.6M的1,2-二甲基-3-丙基咪唑碘,0.1M的碘化锂,0.05M的碘以及0.5M叔丁基吡啶作支持电解质。在AM1.5-100mW/cm2的光强下进行测试,电池的开路电压(Voc)为720mV,短路电流密度(Jsc)为14.2mAcm-2,填充因子(FF)为0.69,光电转换效率为7.05%。其光电流光电压曲线见图3。
结合图1和图3可以看出:本发明所制备的三苯胺-苯基类有机染料作为染料敏化太阳能电池的光敏化剂具有很好的光电转换性能。
Claims (3)
2.一种所述三苯胺-苯基类有机染料的制备方法,其特征在于:采用二芳醛、叔丁醇钾、烷氧基取代三苯胺苄基三苯基膦盐作为原料,依次经魏悌息反应和缩合反应得到目标产物,其合成路线如下所示:
具体步骤如下:
1)烷氧基取代三苯胺苄基三苯基膦盐与二芳醛通过魏悌息反应得到烷氧基取代三苯胺苄基芳醛VI;
2)将烷氧基取代三苯胺苄基芳醛VI,醋酸铵和氰基乙酸置于冰乙酸中,回流条件下反应4小时,冷却后将反应液倒入冰水中,过滤得到固体粗产品,粗产品经柱层析分离得到烷氧基取代三苯胺苄基芳基酸VII。
3.一种所述三苯胺-苯基类有机染料的应用,其特征在于:作为染料敏化太阳能电池的光敏化剂,所述染料敏化太阳能电池包括导电玻璃、二氧化钛膜、光敏化剂、电解质和铂层,所述电解质的配方为在乙腈溶剂中,加入0.6M的1,2-二甲基-3-丙基咪唑碘、0.1M的碘化锂、0.05M的碘和0.5M叔丁基吡啶。
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CN102643558A (zh) * | 2012-01-20 | 2012-08-22 | 华东师范大学 | N-羧甲基吡啶内盐有机染料及其制备和应用 |
CN102924958A (zh) * | 2012-11-15 | 2013-02-13 | 黑龙江中天恒基房地产开发集团有限公司 | 一种三苯胺基有机染料及其合成方法和应用 |
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CN113200957A (zh) * | 2021-04-09 | 2021-08-03 | 西安工业大学 | 一种酸/碱染料共敏体系及其制备方法和应用 |
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