CN108440988A - 一种多氮杂环超分子敏化剂及其应用 - Google Patents
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Abstract
本发明公开了一种多氮杂环超分子敏化剂及其应用，该敏化剂以多氮杂环衍生物为敏化剂的电子供体，通过结构中的‑N＝基团与羧酸类小分子的分子间氢键形成超分子敏化剂，其结构式为其中…‥表示分子间氢键。本发明的多氮杂环超分子敏化剂分子组装简单，结构立体性强，可用于制备较高光电转换效率的太阳能电池。
Description
技术领域
本发明属于敏化剂技术领域，具体涉及一种多氮杂环超分子敏化剂及其应用。
背景技术
随着科技的飞速发展，与日俱增的能源需求与日渐衰竭的能源储备之间的矛盾愈演愈烈。因此，世界各国政府均把目光投向了新能源的开发和利用。无疑，取之不竭、用之不尽的太阳能成为新能源开发利用最活跃的领域。如何高效地将太阳能转化为电能，就成为了这一课题的核心。
染料敏化太阳能电池是以低成本的纳米二氧化钛和敏化剂为主要原料，将太阳能转化为电能。其中，敏化剂是太阳能电池俘获光能的关键，其性能的优劣直接决定电池的光电转换效率。
目前，敏化剂主要分为金属络合物敏化剂和有机敏化剂两大类。与前者比起来，有机敏化剂因其成本低廉、原料易得、摩尔吸光系数高等优点获得了研究者的广泛关注。通常，有机敏化剂由电子供体、共轭桥链和电子受体三部分组成，即D-π-A构型敏化剂。供体部分主要有：腙(Dyes and Pigments 2015,114,175-183)、咔唑(Dyes and Pigments 2014,100,269-277)、香豆素(Dyes and Pigments 2013,99(1),127-135)和三苯胺(ChemicalCommunications 2009,5483-5495)等。普遍认为，作为供体的化合物通常都含有富电子的氮原子，其优势在于优良的供电能力和快速的电子迁移能力。然而，多氮杂环的扁平状结构和分子间作用易引起分子间团聚，因此影响开路电压和光电转换效率的提高。通常，增强分子的立体构型抑制分子间团聚是一个有效解决手段。
发明内容
本发明所要解决的技术问题在于提供一种具有较强立体构型的多氮杂环超分子敏化剂，以及该超分子敏化剂在制备染料敏化太阳能电池中的用途。
解决上述技术问题所采用的多氮杂环超分子敏化剂的结构式如下所示：
结构式中…‥表示分子间氢键。
上述多氮杂环超分子敏化剂的合成路线和具体合成方法如下：
1、制备化合物c
将化合物a、化合物b、四丁基溴化铵、双(二叔丁基-4-二甲氨基苯基膦)氯化钯、NaF按摩尔比为1:1.1:0.03:0.01:2.5加入N,N-二甲基甲酰胺和蒸馏水的混合液中，在75℃反应5小时，停止反应，将反应液降至室温后倒入二氯甲烷中，用水洗至中性，有机相经无水硫酸镁干燥，过滤、减压浓缩、纯化，制备成化合物c。
2、制备前驱体敏化剂d
在氮气保护下，将化合物c、氰基乙酸、乙酸铵按摩尔比为1:2.5:3加入冰乙酸中，搅拌，回流反应5小时，停止反应，将反应液倒入蒸馏水中析出固体，过滤，纯化，制备成前驱体敏化剂d。
3、制备多氮杂环超分子敏化剂e
将前驱体敏化剂d和4-叔丁基苯甲酸按摩尔比为1:3溶解于四氢呋喃中，即可得到多氮杂环超分子敏化剂e。
本发明多氮杂环超分子敏化剂在制备染料敏化太阳能电池中的用途，其具体使用方法与申请号为201310343718.6、发明名称为《硫脲供体双桥链有机染料及其应用》的发明专利申请中公开的使用方法相同。
本发明多氮杂环超分子敏化剂分子组装简单，结构立体性强，制备的太阳能电池光电转换效率比前驱体敏化剂明显改善。试验结果表明，采用本发明多氮杂环超分子敏化剂制备的太阳能电池的光电转换效率相比于相应前驱体敏化剂提高了14.6％。
附图说明
图1是前驱体敏化剂d和超分子敏化剂e在四氢呋喃溶液中的紫外可见吸收图谱。
图2是前驱体敏化剂d和超分子敏化剂e在四氢呋喃溶液中的荧光光谱图(激发波长为450nm)。
具体实施方式
下面结合附图和实施例对本发明进一步详细说明，但本发明的保护范围不限于这些实施例。
实施例1
制备多氮杂环超分子敏化剂e，具体合成方法如下：
1、制备化合物c
向100mL三口瓶中依次加入化合物a(1.0g，2.58mmol)、化合物b(675mg，2.83mmol)、四丁基溴化铵(250mg，0.78mmol)、双(二叔丁基-4-二甲氨基苯基膦)氯化钯(20mg，0.03mmol)、NaF(270mg，6.44mmol)加入N,N-二甲基甲酰胺(40mL)和蒸馏水(8mL)的混合液中，在75℃反应5小时，停止反应，将反应液降至室温后倒入二氯甲烷(150mL)中，用水洗至中性，有机相经无水硫酸镁干燥，过滤、减压浓缩、柱层析，制备成黄色固体化合物c0.85g,收率为65.8％。
所制备的化合物c的核磁数据为：1H NMR(400MHz,THF-d8):δ(ppm)9.87(s,1H),8.87(d,J＝8.5Hz,2H),8.84-8.81(m,4H),7.94(d,J＝8.5Hz,2H),7.84(d,J＝3.9Hz,1H),7.67(d,J＝3.9Hz,1H),7.65-7.58(m,6H),7.55(d,J＝3.9Hz,1H),7.49(d,J＝3.9Hz,1H).
2、制备前驱体敏化剂d
在氮气保护下，向100mL三口烧瓶中依次加入化合物c(750mg，1.50mmol)、冰乙酸(50mL)、氰基乙酸(343mg，4.04mmol)和乙酸铵(346mg，4.49mmol)，搅拌，回流反应5小时，停止反应，降温后将反应液缓慢倒入蒸馏水中，有固体析出，过滤，柱层析，得到暗红色固体，即前驱体敏化剂d0.54g，收率为63.5％。
所制备的前驱体敏化剂d的核磁数据为：1H NMR(400MHz,THF-d8):δ(ppm)8.83-8.79(m,6H),8.36(s,1H),7.91(d,J＝8.5Hz,2H),7.81(d,J＝4.1Hz,1H),7.65(d,J＝3.9Hz,1H),7.63-7.58(m,6H),7.56(d,J＝3.9Hz,1H),7.47(d,J＝4.0Hz,1H).
3、制备多氮杂环超分子敏化剂e
将7.13mg(0.04mmol)前驱体敏化剂d和69.00mg(0.12mmol)4-叔丁基苯甲酸溶解于100mL四氢呋喃中，得到多氮杂环超分子敏化剂e的四氢呋喃溶液。
采用紫外可见近红外测试仪(Shimadzu UV-3600)对前驱体敏化剂d的四氢呋喃溶液和多氮杂环超分子敏化剂e的四氢呋喃溶液进行紫外可见吸收性能测试，结果见图1。前驱体敏化剂d和多氮杂环超分子敏化剂e的最大吸收波长均为410nm，吸收强度分别为4.20×10-4/M-1 cm-1和5.07-4/M-1 cm-1。相比前驱体敏化剂d，多氮杂环超分子敏化剂e的紫外可见吸收强度提高了20.7％，这是由于4-叔丁基苯甲酸中的-COOH基团与前驱体敏化剂d中的-N＝基团之间形成分子间氢键，抑制了极性溶剂四氢呋喃和-N＝基团之间的相互作用(ACS appliedmaterials&interfaces 2017,9(7),6255-6264)。
采用荧光光谱仪(Hitachi F-7000)对前驱体敏化剂d的四氢呋喃溶液和多氮杂环超分子敏化剂e的四氢呋喃溶液进行荧光性能测试，结果见图2。由图可见，激发波长为450nm时，最大吸收波长均为515nm，相应的荧光强度分别为995.8a.u.和879.7a.u.。相比前驱体敏化剂d，多氮杂环超分子敏化剂e的荧光强度降低11.64％，这是分子间氢键引起的荧光猝灭现象(Tetrahedron 2005,61(36),8686-8693；Carbon 2006,44(13),2785-2792)。
总之，通过图1和图2的结果互相验证了前驱体敏化剂d中的-N＝基团和4-叔丁基苯甲酸中的-COOH基团之间通过分子间氢键形成了超分子敏化剂e。
通过Gaussian 03软件(B3LYP/6-311G(d,p)level)，采用密度泛函理论计算获得前驱体敏化剂d和多氮杂环超分子敏化剂e的三维立体构型及分子尺寸分别为和说明该超分子敏化剂具有更强的立体构型。
实施例2
实施例1的多氮杂环超分子敏化剂e在制备染料敏化太阳能电池中的用途，其具体使用方法与申请号为201310343718.6、发明名称为《硫脲供体双桥链有机染料及其应用》的发明专利申请中公开的使用方法相同。同时以实施例1中的化合物d做对比试验。采用J-V特性测试系统(CROWNTECH IV Test Station 2000)对制备的太阳能电池进行测试，结果见表1。
表1 太阳能电池性能测试结果
由表1可见，与其前驱体敏化剂d相比，采用多氮杂环超分子敏化剂e制备的太阳能电池的光电转化效率提高了14.6％。
Claims (2)
1.一种多氮杂环超分子敏化剂，其特征在于该敏化剂的结构式如下所示：
结构式中…‥表示分子间氢键。
2.权利要求1所述的多氮杂环超分子敏化剂在制备染料敏化太阳能电池中的用途。
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