CN109280051A - 一种色酮类化合物的制备及其在染料敏化太阳能电池中的应用 - Google Patents
一种色酮类化合物的制备及其在染料敏化太阳能电池中的应用 Download PDFInfo
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- CN109280051A CN109280051A CN201811117989.9A CN201811117989A CN109280051A CN 109280051 A CN109280051 A CN 109280051A CN 201811117989 A CN201811117989 A CN 201811117989A CN 109280051 A CN109280051 A CN 109280051A
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/008—Triarylamine dyes containing no other chromophores
-
- 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
- H01G9/20—Light-sensitive devices
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/542—Dye sensitized solar cells
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Power Engineering (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Hybrid Cells (AREA)
Abstract
本发明涉及一系列新的色酮和硫色酮化合物，该类化合物具有如式（I）的结构，X为O或S原子。其中R2选自羟基、巯基、C1‑C6的烃氧基、C1‑C6的烃硫基、苯氧基、苯硫基、被1个或多个C1‑C6烃氧基取代的苯氧基及苯硫基。R3选自五元氮唑环中的一种；R4、R5、R7分别独立地选自氢、氟、氯、溴或碘；R6选自氢、氟、氯、溴、碘、C1‑C6的烃氧基、C1‑C6的烃氨基、C1‑C6的烃基、苯氧基、被1个或多个C1‑C6烃氧基取代的苯氧基。本发明(I)结构具有一定的光敏性，可以用于染料敏化太阳能电池。实验表明，用这类化合物敏化的太阳能电池最高的光转化效率可达到6.17％。
Description
技术领域
本发明涉及一系列色酮及硫色酮染料的合成及其在染料敏化太阳能电池中的应用。
背景技术
染料敏化太阳电池(DSSCs)是一种新型光电化学太阳能电池，制作工艺简单、成本低廉和性能稳定，并且对环境污染很小。其主要由纳米多孔半导体薄膜、染料敏化剂、氧化还原电解质、对电极和导电基底等几部分组成。纳米多孔半导体薄膜通常为金属氧化物(TiO2、SnO2、ZnO等)，聚集在有透明导电膜的玻璃板上作为DSC的负极。对电极作为还原催化剂，通常在带有透明导电膜的玻璃上镀上铂。敏化染料吸附在纳米多孔二氧化钛膜面上。正负极间填充的是含有氧化还原电对的电解质，最常用的是I3 -/I-。这一新型太阳电池有着比硅电池更为广泛的用途：如可用塑料或金属薄板使之轻量化，薄膜化；可使用各种色彩鲜艳的染料使之多彩化；另外，还可设计成各种形状的太阳能电池使之多样化。总之染料敏化纳米晶太阳能电池有着十分广阔的产业化前景，是具有相当广泛应用前景的新型太阳电池。相信在不久的将来，染料敏化太阳电池将会走进我们的生活。
自从1991年Gratzel等人研究出转化率达到7.1％的DSSCs之后，染料敏化太阳能电池受到了广泛的关注。经过短短十几年时间，染料敏化太阳电池研究在染料、电极、电解质等各方面取得了很大进展。同时在高效率、稳定性、耐久性、等方面还有很大的发展空间。
目前常见的敏化剂一共有四种，包括：钌基多吡啶有机金属配合物、酞菁和菁类染料、“固体染料”和天然染料。王洪涛等研究了29种植物提取的天然染料的敏化性能，发现其中黄酮类化合物染料的敏化效果较好，其最高的转化效率可达2.13％。
为设计并合成出更加高效的敏化剂，根据结构修饰理论，我们对α-氮唑邻卤苯乙酮进行结构修饰，合成了一系列的色酮以及硫色酮化合物，并将其用于染料敏化太阳能电池。
发明内容
本发明提供了具有式(I)结构的一系列2-取代-3-氮杂环色酮类化合物的合成以及其在染料敏化太阳能电池中的应用。
本发明所涉及的2-羟基-3-氮杂环色酮及硫色酮类化合物，其化学结构如下：
其中，X表示O或S。
R2选自羟基、巯基、C1-C6的烃氧基、C1-C6的烃硫基、苯氧基、苯硫基、被1个或多个C1-C6烃氧基取代的苯氧基及苯硫基。
R3选自如式(II)五元氮唑环中的一种：
其中：J、K、L分别独立地选自氢、C1-C3的烃基；
R4、R5、R7分别独立地选自氢、氟、氯、溴或碘；
R6选自氢、氟、氯、溴、碘、C1-C6的烃氧基、C1-C6的烃氨基、C1-C6的烃基、苯氧基、被1个或多个C1-C6烃氧基取代的苯氧基；
式(I)化合物的合成方法，是将化合物(III)溶于有机溶剂中，分别与二氧化碳气体或者二硫化碳反应，关环后生成化合物(IV)，调酸得到化合物(I)。
所述化合物(III)的结构式如下：
其中X表示F或Cl。
所述化合物(IV)的结构式如下：
其中，X表示O或S；
R2、R3、R4、R5、R6、R7的定义同式(I)；
所述有机溶剂选自N，N-二甲基甲酰胺、N，N-二甲基乙酰胺、二甲亚砜、二氧六环、乙腈、四氢呋喃中的至少一种。优选N，N-二甲基甲酰胺、二甲亚砜。
所述碱性化合物选自碱金属碳酸盐、碱金属氢氧化物、碱金属醋酸盐或三乙胺、二乙基异丙胺、N-甲基哌啶、N-乙基哌啶、N-甲基吗啉、N-乙基吗啉、吡啶、4-甲基吡啶中的至少一种。优选碳酸钾、碳酸铯、无水乙酸钠。
该反应可以采用各步生成物不经分离而直接进入下一步反应的一步合成法或将每步反应的生成物进行分离纯化后进入下一步反应的分步合成法。
本发明的合成方法是一种通用方法，适合于合成色酮以及硫色酮化合物及其衍生物，对芳环上的多种官能团具有高的容忍度，因此事实上对色酮或硫色酮类化合物及其衍生物中的取代基个数和种类并无特别限制。
本发明提供所述2-取代-3-氮杂环硫色酮类化合物以及2-羟基-3-氮杂环色酮类化合物可用于染料敏化太阳能电池的敏化剂。通过对组装而成的染料敏化太阳能电池进行性能测试，我们对合成的一系列色酮和硫色酮化合物的敏化性能进行了评价。试验证明，本发明合成的两类化合物具有较好的敏化性能。
具体实施方式
下面通过具体实施例对本发明的合成方法进行说明。应当注意到，这里给出的描述和实施例仅仅是为了描述本发明的具体实施方式，使技术人员更容易理解本发明，它们并非意欲限定本发明的范围。
实施例1，式(I)2-羟基-3-氮杂环色酮的合成制备反应式如下：
制备步骤如下：
单口烧瓶中加入1-(2，4-二氟苯基)-2-(1，2，4-三氮唑-1-基乙酮18.4mmol，DMSO50mL、K2CO3 92mmol，18-冠醚-6 18.4mmol，通入二氧化碳气体常温下搅拌10h。反应毕，将反应液倒入50mL水中，用稀盐酸调pH至酸性，析出固体，抽滤得到类白色固体，无水甲醇重结晶得式(I1)产物2-羟基-3-(1，2，4-三氮唑-1-基)-7氟色酮-14.9mmol，收率81％。
1H NMR(400MHz，DMSO-d6)：12.23(s，1H)，9.16(s，1H)，8.53(s，1H)，7.97～8.01(m，1H)，7.36～7.39(m，1H)，7.22～7.27(m，1H)。
实施例2，式V1的合成制备反应式如下：
制备步骤如下：
单口烧瓶中加入1-(2，4-二氯-5-氟苯基)-2-(4-甲基吡唑-1-基)乙酮18.4mmol，DMSO 30mL、NaOH 43mmol，搅拌下升温至40℃，在此温度下滴加CS222.8mmol的5mL DMSO的溶液。滴毕，控温40℃搅拌反应。反应毕，冷却至室温，滴加碘乙烷25.6mmol的10mL DMSO溶液，滴毕，室温反应至反应毕，将反应液搅拌下倒入50mL冰水中，有大量固体析出，过滤收集固体，乙醇中重结晶，得式(V1)产物2-乙硫基-3-(4-甲基吡唑-1-基)-6-氟-7氯硫色酮--14.0mmol，收率76％。
1H NMR(300MHz，DMSO)6＝8.48(d，1H)，8.16(d，1H)，7.54(d，2H)，3.26(q，2H)，2.12(s，3H)，1.33(t，3H).
实施例3～实施例9中，产物式(I)2-羟基-3-氮唑环色酮类化合物各基团选择及检测数据均列于表1：
表1：
案例22：染料敏化太阳能电池组装和测试
1、试验药品及仪器
试验用材料及仪器：ITO玻璃电极片、电化学工作站、氙光灯、匀胶机试验用药品：钛酸四丁酯、乙醇、二乙醇胺、磷酸三丁酯、碘化钠、碘单质
2、实验方法：
(1)染料溶液的配置
称取一定量的染料，将其加入到无水乙醇中，配置成浓度为0.01mol/L的溶液，用保鲜膜封存备用。
(2)二氧化钛溶胶的制备
在100mL单口烧瓶中加入钛酸丁酯10mL，加入无水乙醇20mL，搅拌30分钟后，想溶液中缓慢加入2mL水和10mL乙醇的混合溶液。搅拌3小时后，加入PEG-1000，继续搅拌3小时，然后打开瓶塞，陈化过夜，得到二氧化钛溶胶。
(3)薄膜电极的制备
将ITO导电面清晰干净，设置匀胶机转速为2000转，利用旋涂法在电极上镀上一层薄膜。设置马弗炉的温度为450℃，缓慢升温，烧结30分钟。待电极降温到80设施度时将其避光浸泡在制备的染料中24小时。
(5)电解质液的制备
称取0.375g碘化钠，0.1g碘单质，20mL乙腈以及5mL磷酸三丁酯加入50mL烧杯，搅拌均匀。
(6)电池参数的测量
将ITO玻璃电极与铂电极组成电池，在电化学工作站上测量其短路电流以及开路电压，计算其填充因子以及转化效率。
3、染料敏化太阳能电池测试结果
Claims (9)
1.一种如式(I)的2-取代-3-氮杂环硫色酮类化合物，其化学结构如下：
其中X为O或S；
R2选自羟基、巯基、C1-C6的烃氧基、C1-C6的烃硫基、苯氧基、苯硫基、被1个或多个C1-C6烃氧基取代的苯氧基及苯硫基。
R3选自如式(II)五元氮唑环中的一种：
其中：J、K、L分别独立地选自氢、C1-C3的烃基；
R4、R5、R7分别独立地选自氢、氟、氯、溴或碘；
R6选自氢、氟、氯、溴、碘、C1-C6的烃氧基、C1-C6的烃氨基、C1-C6的烃基、苯氧基、被1个或多个C1-C6烃氧基取代的苯氧基。
2.根据权利要求1所述的化合物，其特征该化合物包含其在制剂学上所容许的盐。
3.一种权利要求1的式(I)原子的化合物的合成方法，其特征是，将化合物(III)溶于有机溶剂中，当X为O时，在二氧化碳环境下反应，经缩合、关环后与C1-C6的卤代烃反应生成2-取代-3-氮杂环色酮类化合物，当X为S时，化合物(III)在二硫化碳环境下反应，经缩合、关环后与C1-C6的卤代烃反应生成化合物(V)经氧化剂氧化生成化合物(VI)，然后在碱性化合物条件下和R2H反应，得到固体产品2-取代-3-氮杂环硫色酮
所述化合物(III)的结构式如下：
其中，X为Cl或F；
所述化合物(V)的结构式如下：
所述化合物(VI)的结构式如下：
R2、R3、R4、R5、R6、R7的定义同式(I)；
R8选自C1-C6的烃基。
4.根据权利要求3所述的合成方法，其特征是所述有机溶剂选自N，N-二甲基甲酰胺、N，N-二甲基乙酰胺、二甲亚砜、二氧六环、乙腈、四氢呋喃、甲醇、乙醇、异丙醇、叔丁醇中的至少一种；所述氧化剂选自二氧化锰、高锰酸钾、重铬酸钾、过氧化氢、过氧苯甲酸、间氯过氧苯甲酸、单过氧邻苯二甲酸镁或过氧乙酸中的至少一种；所述碱性化合物选自碱金属碳酸盐、碱金属氢氧化物、碱金属醋酸盐或三乙胺、二乙基异丙胺、N-甲基哌啶、N-乙基哌啶、N-甲基吗啉、N-乙基吗啉、；吡啶、4-甲基吡啶中的至少一种。
5.根据权利要求3、4所述的合成方法，其特征是所述有机溶剂选自N，N-二甲基甲酰胺、二甲亚砜；所述氧化剂选自过氧化氢、间氯过氧苯甲酸；所述碱性化合物选自氢氧化钠、氢氧化钾、碳酸钾、碳酸铯。
6.根据权利要求3-5所述的合成方法，其特征是每步反应生成物不经分离而直接进入下一步反应的一步合成法或将每步反应的生成物进行分离纯化后进入下一步反应的分步合成法。
7.一种权利要求1所述2-取代-3-氮杂环硫色酮类化合物以及2-取代-3-氮杂环色酮类化合物作为光敏剂用于染料敏化太阳能电池。
8.用权利要求7所述的有机染料制备染料敏化太阳能电池，其特征在于，由ITO玻璃电极(1)、光吸收层(2)、还原层(3)和对电极(4)组成。
所述的光吸收层(2)是由纳米粒子和染料层构成，其中纳米粒子层与ITO玻璃电极相连；染料层与还原层(3)相连。
所述的纳米粒子层是由Si、TiO2、ZnO中的任意一种构成，0nm＜纳米颗粒平均直径＜100nm；
所述的染料层为具有化学结构通式I的有机染料构成；
所述的还原层(3)是由碘单质、碘盐、磷酸三丁酯以及表面活性剂构成；
所述的表面活性剂包括：聚乙二醇-400，聚乙二醇-1000以及聚乙二醇-2000
所述的对电极(4)为Pt、C、ITO玻璃、Ag、Cu以及导电聚合物中的任意一种或者多种。
9.根据权利要求8所述的有机化合物染料敏化太阳能电池，其染料在可见光区域以及紫外光区域均有良好的吸收，最高的光转化效率达到了6.17％。
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