CN105777613A - 一种含芴酮的n-丁基咔唑类化合物及其制备方法和应用 - Google Patents
一种含芴酮的n-丁基咔唑类化合物及其制备方法和应用 Download PDFInfo
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- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 title claims abstract description 30
- 238000002360 preparation method Methods 0.000 title claims abstract description 20
- SQFONLULGFXJAA-UHFFFAOYSA-N 9-butylcarbazole Chemical class C1=CC=C2N(CCCC)C3=CC=CC=C3C2=C1 SQFONLULGFXJAA-UHFFFAOYSA-N 0.000 title abstract 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 53
- 238000006243 chemical reaction Methods 0.000 claims abstract description 13
- 238000003756 stirring Methods 0.000 claims abstract description 7
- -1 N-butyl carbazole compound Chemical class 0.000 claims description 35
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 28
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 26
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
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- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 6
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- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
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- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
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- YOFHQTKNQIMLKB-UHFFFAOYSA-N 1-bromo-9-butylcarbazole Chemical compound BrC1=CC=CC=2C3=CC=CC=C3N(C1=2)CCCC YOFHQTKNQIMLKB-UHFFFAOYSA-N 0.000 description 2
- FYEFHYMUEWRCRF-UHFFFAOYSA-N 2,7-dibromofluoren-1-one Chemical compound BrC1=CC=C2C3=CC=C(Br)C(=O)C3=CC2=C1 FYEFHYMUEWRCRF-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 150000003851 azoles Chemical class 0.000 description 2
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- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 2
- MLSKXPOBNQFGHW-UHFFFAOYSA-N methoxy(dioxido)borane Chemical compound COB([O-])[O-] MLSKXPOBNQFGHW-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
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- 229930192474 thiophene Natural products 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- VXWBQOJISHAKKM-UHFFFAOYSA-N (4-formylphenyl)boronic acid Chemical compound OB(O)C1=CC=C(C=O)C=C1 VXWBQOJISHAKKM-UHFFFAOYSA-N 0.000 description 1
- HEULOCRFYUTVLU-UHFFFAOYSA-N 1-(4-bromobutyl)-9h-carbazole Chemical compound C12=CC=CC=C2NC2=C1C=CC=C2CCCCBr HEULOCRFYUTVLU-UHFFFAOYSA-N 0.000 description 1
- 229920001651 Cyanoacrylate Polymers 0.000 description 1
- 229910002621 H2PtCl6 Inorganic materials 0.000 description 1
- 241001597008 Nomeidae Species 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 244000170916 Paeonia officinalis Species 0.000 description 1
- 235000006484 Paeonia officinalis Nutrition 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 238000006069 Suzuki reaction reaction Methods 0.000 description 1
- 229910003074 TiCl4 Inorganic materials 0.000 description 1
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- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
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- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
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- 229910052739 hydrogen Inorganic materials 0.000 description 1
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
- 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
- C07D405/10—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 linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- H01G9/2059—Light-sensitive devices comprising an organic dye as the active light absorbing material, e.g. adsorbed on an electrode or dissolved in solution
-
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Power Engineering (AREA)
- Materials Engineering (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
本发明涉及一种含芴酮的N‑丁基咔唑类化合物及其制备方法和应用。它以如式(IV)所示的化合物与如式(V)所示的化合物为原料,在碱性化合物的作用下,加热回流搅拌反应一定时间,反应完全后,经过滤、柱层析获得咔唑类化合物,其反应条件温和、对设备要求低、操作简单,得到的产品结构经核磁共振等认证,该化合物作为染料敏化剂组装成的染料敏化太阳能电池具有较好的光电转换效率,为染料敏化剂的筛选增添了新的可应用物质。
Description
技术领域
本发明涉及一种含芴酮的N-丁基咔唑类化合物及其制备方法和应用。
背景技术
染料敏化太阳能电池(Dye Sensitized Solar Cell,DSSC)凭借其成本低、可弱光发电、光电转化率不受温度影响等特点,极有希望替代硅半导体光电转换部件,成为下一代实用型高性能太阳能电池。染料敏化剂是DSSC中决定可见光吸收和光电转换效率的关键结构材料,具有结构易修饰、加工成本低和稳定性好等特点。
国内外染料敏化剂的研究主要分两类,一类为有机金属配合物,另一类为非金属有机染料。而相比于贵金属敏化剂,有机非金属染料具有分子结构多样、较为廉价、且更加环境友好、摩尔消光系数更高等优点,是近年来染料敏化剂的研究热点。传统的非金属有机染料敏化剂的结构通式为“给体-π共轭桥-受体”(Donor-πBridge-Acceptor,D-π-A)。
咔唑及其衍生物是一类重要的含氮芳杂环化合物,其特殊的刚性稠环结构使其表现出许多独特的性能及生物活性,在光电材料、染料、医药、超分子识别等多领域得以广泛应用。更为重要的是咔唑类化合物易于进行结构修饰,在咔唑环上可方便地引入各种功能基,因而咔唑衍生物的合成及其开拓咔唑类化合物潜在的新用途,成为近些年来十分活跃的研究领域。2008年,Koumura小组报道了一类高效的咔唑敏化剂,系统地研究了N-己基取代的低聚噻吩π桥对组装的染料敏化电池性能的影响;2010年,Yang小组以咔唑作为电子供体,罗丹宁乙酸作为受体,设计合成了一系列咔唑类染料敏化剂,其光电转化效率最高为4.63%;2011年,Tan小组则报道了以连三苯胺的咔唑为敏化剂电子给体,得到高达7.03%的效率。本发明以原料易得的咔唑作为给体,连芳环的芴酮作为桥键,氰乙酸作为受体,设计合成了三个咔唑类染料敏化剂。目前,尚无文献报道该结构的太阳能电池应用。
发明内容
本发明的目的在于提供一种含芴酮的N-丁基咔唑类化合物及其制备方法和应用,具体将其应用于染料敏化太阳能电池。
所述的一种含芴酮的N-丁基咔唑类化合物,其特征在于包括如式(Ⅰ)、式(Ⅱ)及式(III)所示的化合物Ⅰ、化合物Ⅱ和化合物III:
所述的一种含芴酮的N-丁基咔唑类化合物,其特征在于化合物Ⅰ、化合物Ⅱ和化合物III中电子受体为2-氰基丙烯酸。
所述的含芴酮的N-丁基咔唑类化合物的制备方法,其特征在于包括如下步骤:在有机溶剂中,将式(IVa)、式(IVb)、式(IVc)所示的化合物IVa、化合物IVb、化合物IVc分别与式(V)所示的化合物V混合,在碱性化合物的作用下,加热回流搅拌反应1~10h,反应完全后,旋干溶剂,残余物用洗脱剂溶剂进行硅胶柱层析,获得式(I)、式(II)和式(III)所示的化合物Ⅰ、化合物Ⅱ和化合物III;
所述的含芴酮的N-丁基咔唑类化合物的制备方法,其特征在于碱性化合物为哌啶、吡啶、三乙胺或者三甲胺中的一种或多种混合物。
所述的含芴酮的N-丁基咔唑类化合物的制备方法,其特征在于有机溶剂为乙腈、氯仿、四氢呋喃或1,4-二氧六环中的一种或多种混合物。
所述的含芴酮的N-丁基咔唑类化合物的制备方法,其特征在于洗脱剂溶剂为卤代甲烷、醇及醋酸的混合物,所述卤代甲烷为氯仿或二氯甲烷,所所述醇为甲醇或乙醇,优选洗脱剂溶剂为体积比为400:4:1的二氯甲烷、甲醇和醋酸的混合溶剂。
所述的含芴酮的N-丁基咔唑类化合物的制备方法,其特征在于式(IVa~IVc)化合物、式(V)化合物和碱性化合物的物质的量之比为1:1.0~3.0:1.0~4.0;有机溶剂体积用量以式(IVa~IVc)化合物的物质的量计为10~30mL/mmol,优选为15mL/mmol。。
所述的含芴酮的N-丁基咔唑类化合物的制备方法,其特征在于所述反应时间为8~12h,优选为12h。
式(IVa~IVc)所示的化合物可按照以下方法制备得到:将原料VI、VII、和Pd(PPh3)4溶于四氢呋喃中,注入碳酸钾溶液,氮气保护下加热回流制备得到。
化合物VI可按下述方法制备:将溴代N-正丁基咔唑(VIII)溶于THF,-78℃下缓慢注入正丁基锂,低温搅拌之后加入硼酸三甲酯,室温下搅拌22h。直接进行下一步的Suzuki偶联。将2,7-二溴芴酮(IX)和Pd(PPh3)4溶于四氢呋喃中,加入上述溶液和碳酸钾溶液,加热回流制备得到。
上述均为本领域技术人员公知的制备方法。
本发明的咔唑类化合物的合成反应方程式如下:
所述的含芴酮的N-丁基咔唑类化合物作为染料敏化剂在太阳能电池上的应用,具体应用过程为:将含芴酮的N-丁基咔唑类化合物溶于体积比为1:10的CH3OH和CHCl3混合溶剂中,浸泡TiO2纳米粒子膜光电极24h,负载了含芴酮的N-丁基咔唑类化合物的TiO2电极与铂对电极组装成三明治结构,并在边缘滴入电解质,利用毛细管渗透原理引入电池内部,于100mW/cm2光强照射下,测定光电压-电流特性曲线,得含芴酮的N-丁基咔唑类化合物的光电转换效率为4.57-4.88%。
通过采用上述技术,与现有技术相比,本发明的有益效果如下:
1)本发明提供了一种新的含芴酮的N-丁基咔唑类化合物,制备方法简单、反应条件温和、对设备要求低、操作简单,得到的产品结构经核磁共振等认证;
2)本发明得到的含芴酮的N-丁基咔唑类化合物作为染料敏化剂组装成的染料敏化太阳能电池具有较好的光电转换效率,本发明实施例中测得其光电转换效率为4.57-4.88%,为染料敏化剂的筛选增添了新的可应用物质。
具体实施方式
下面结合具体实施例对本发明进行进一步描述,但本发明的保护范围并不仅限于此:
实施例1:化合物(VI)的合成
称取溴代丁基咔唑(6.4mmol,1.96g)放入100mL三口圆底烧瓶中,真空换氮后,注入重蒸过的THF(30mL),冷却到-78℃下搅拌,缓慢注入正丁基锂(3.0mL)低温搅拌1h,之后加入硼酸三甲酯(2.24mL),升至室温下搅拌22h,得到无色混浊反应液,有白色沉淀。加入2,7-二溴芴酮(7mmol,2.38g)、Pd(PPh3)4(0.65mmol,0.74g)和碳酸钾水溶液(13mL,2mol/L),加热回流12h。反应冷至室温,加水稀释,二氯甲烷萃取3次,合并有机层,无水Na2SO4干燥。柱层析(VPE:VCH2Cl2=5:1)分离得深橙色固体2.61g,收率85.0%。m.p.196~198℃;1H NMR(CDCl3,500MHz)δ:8.34(d,J=1.6Hz,1H),8.16(d,J=7.7Hz,1H),8.03(d,J=1.5Hz,1H),7.86(dd,J=7.7,1.8Hz,1H),7.79(d,J=1.8Hz,1H),7.73(dd,J=8.5,1.8Hz,1H),7.63(dd,J=7.9,1.9Hz,1H),7.59(d,J=7.7Hz,1H),7.51(dd,J=7.5,1.1Hz,1H),7.48(d,J=8.5Hz,1H),7.45(d,J=8.2Hz,1H),7.41(d,J=7.41Hz,1H),7.31-7.28(m,1H),4.35(t,J=7.2Hz,2H),1.94-1.86(m,2H),1.48-1.40(m,2H),0.98(t,J=7.4Hz,3H).
实施例2:化合物(IVa)的合成
化合物VI(2.5mmol,1.2g)、4-甲酰基苯硼酸(3mmol,0.45g)和Pd(PPh3)4(0.25mmol,0.29g)混合后真空换氮,加入四氢呋喃(20mL)和碳酸钾溶液(5mL,2mol/L)。加热回流12h后得到深红色反应溶液,继续回流10h后反应液变为黑色。冷至室温,加水稀释,二氯甲烷萃取3次,合并有机层,无水Na2SO4干燥。柱层析(VPE:VCH2Cl2=2:1)分离得橙红色固体1.19g,收率94%。m.p.195~197℃;1H NMR(500MHz,CDCl3)δ:10.08(s,1H),8.37(d,J=1.6Hz,1H),8.17(d,J=7.7Hz,1H),8.07(d,J=1.5Hz,1H),8.00-7.97(m,3H),7.89(dd,J=7.7,1.7Hz,1H),7.84-7.77(m,3H),7.76(dd,J=8.4,1.8Hz,1H),7.65(d,J=7.7Hz,2H),7.57-7.48(m,2H),7.45(d,J=8.2Hz,1H),7.30(d,J=7.5Hz,1H),4.35(t,J=7.2Hz,2H),2.09-1.79(m,2H),1.51-1.36(m,2H),0.99(t,J=7.4Hz,3H).
实施例3:化合物(IVb)的合成
化合物VI(3.4mmol,1.63g)、4-甲酰基呋喃硼酸(6.8mmol,0.95g)和Pd(PPh3)4(0.34mmol,0.39g)混合后真空换氮,加入四氢呋喃(106mL)和碳酸钾溶液(6.8mL,2mol/L)。加热回流12h。冷至室温,加水稀释,二氯甲烷萃取3次,合并有机层,无水Na2SO4干燥。柱层析(VPE:VCH2Cl2=2:1)分离得橙红色固体0.88g,收率52%。m.p.166~168℃;1H NMR(500MHz,CDCl3)δ:9.69(s,1H),8.37(d,J=1.6Hz,1H),8.17(d,J=7.7Hz,1H),8.08(d,J=1.3Hz,2H),8.03(dd,J=7.8,1.6Hz,1H),7.90(dd,J=7.8,1.7Hz,1H),7.75(dd,J=8.5,1.8Hz,1H),7.65(t,J=8.1Hz,2H),7.51(dd,J=16.0,7.9Hz,2H),7.45(d,J=8.2Hz,1H),7.36(d,J=3.7Hz,1H),7.30(d,J=7.2Hz,1H),6.93(d,J=3.7Hz,1H),4.35(t,J=7.2Hz,2H),1.93-1.87(m,2H),1.48-1.41(m,2H),0.98(t,J=7.4Hz,3H).
实施例4:化合物(IVc)的合成
化合物VI(3.4mmol,1.63g),Pd(PPh3)4(0.34mmol,0.39g),4-甲酰基噻吩硼酸(6.8mmol,1.06g)混合后真空换氮,加入四氢呋喃(106mL)和碳酸钾溶液(6.8mL,2mol/L)。加热回流12h。冷至室温,加水稀释,二氯甲烷萃取3次,合并有机层,无水Na2SO4干燥。柱层析(VPE:VCH2Cl2=2:1)分离得橙红色固体0.1g,收率6%。m.p.151~153℃;1H NMR(500MHz,CDCl3)δ:8.37(d,J=1.6Hz,1H),8.18(d,J=7.6Hz,1H),8.07(d,J=1.4Hz,1H),7.95(d,J=1.4Hz,1H),7.87(dd,J=7.7,1.8Hz,1H),7.76(d,J=1.7Hz,1H),7.75(d,J=1.8Hz,1H),7.62(d,J=7.7Hz,1H),7.56(d,J=7.8Hz,1H),7.54-7.48(m,2H),7.45(d,J=8.2Hz,1H),7.41(dd,J=3.6,1.1Hz,1H),7.34(dd,J=5.1,1.1Hz,1H),7.31-7.29(m,1H),7.13(dd,J=5.1,3.6Hz,1H),4.36(t,J=7.2Hz,2H),1.95-1.87(m,2H),1.49-1.41(m,2H),0.99(t,J=7.4Hz,3H).
实施例5:化合物(I)的合成
实施例5-1:IVa(0.40mmol,0.2g)、氰基乙酸(0.84mmol,0.07g)和哌啶(0.16mL,1.6mmol)溶于氯仿(6mL)中,氮气保护下加热回流12h,反应液冷至室温,直接旋干,柱层析(VCH2Cl2:VCH3OH:VHAc=400:4:1)分离得橙红色固体0.17g,收率74%。m.p.249~251℃;1H NMR(500MHz,d-DMSO)δ:14.03(s,1H),8.63(d,J=1.3Hz,1H),8.37(s,1H),8.31(d,J=7.7Hz,1H),8.14(d,J=8.5Hz,2H),8.07-7.99(m,6H),7.94(dd,J=7.7,4.5Hz,2H),7.85(dd,J=8.6,1.5Hz,1H),7.68(d,J=8.6Hz,1H),7.62(d,J=8.3Hz,1H),7.48(t,J=7.6Hz,1H),7.23(t,J=7.4Hz,1H),4.42(t,J=7.0Hz,2H),1.80-1.74(m,2H),1.35-1.28(m,2H),0.89(t,J=7.4Hz,3H);HRESIMS m/z 571.2003[M-H]-,cacld C39H28N2O3for:572.2100。
上述实施例中,碱性化合物用哌啶、吡啶、三乙胺或者三甲胺中的一种或多种混合物代替哌啶,有机溶剂用为乙腈、氯仿、四氢呋喃或1,4-二氧六环中的一种或多种混合物代替氯仿,洗脱剂溶剂用其他卤代甲烷、醇及醋酸的混合物代替二氯甲烷、甲醇和醋酸的混合溶剂,均能取得同样的技术效果。
实施例5-2:IVa(0.40mmol,0.2g)、氰基乙酸(0.40mmol,0.03g)和哌啶(0.04mL,0.4mmol)溶于氯仿(4mL)和乙腈(4mL)中,氮气保护下加热回流8h,反应液冷至室温,直接旋干,柱层析(VCHCl3:VCH3OH:VHAc=400:4:1)分离得橙红色固体0.1g,收率45%。
实施例5-3:IVa(0.40mmol,0.2g)、氰基乙酸(1.20mmol,0.1g)和吡啶(0.03g,0.4mmol)和三乙胺(0.08g,0.8mmol)溶于THF(4mL)中,氮气保护下加热回流10h,反应液冷至室温,直接旋干,柱层析(VCH2Cl2:VEtOH:VHAc=400:4:1)分离得橙红色固体0.04g,收率18%。
实施例5-4:IVa(0.40mmol,0.2g)、氰基乙酸(0.84mmol,0.07g)和三甲胺(0.07g,1.2mmol)溶于二氧六环(12mL)中,氮气保护下加热回流6h,反应液冷至室温,直接旋干,柱层析(VCH2Cl2:VEtOH:VHAc=400:4:1)分离得橙红色固体0.09g,收率41%。
实施例6:化合物(II)的合成
实施例6-1:IVb(0.40mmol,0.2g)、氰基乙酸(0.84mmol,0.07g)和哌啶(0.16mL,1.6mmol)溶于氯仿(6mL)中,氮气保护下加热回流12h。反应液冷至室温,直接旋干,柱层析(VCH2Cl2:VCH3OH:VHAc=400:4:1)分离得深红色固体0.19g,收率85%。m.p.238~241℃;1H NMR(500MHz,d-DMSO)δ:13.65(s,1H),8.64(s,1H),8.32(d,J=7.7Hz,1H),8.17(s,1H),8.14(d,J=7.8Hz,1H),8.09-8.08(m,1H),8.05(s,1H),8.00(d,J=7.8Hz,1H),7.95(d,J=7.8Hz,1H),7.87(d,J=8.6Hz,1H),7.68(d,J=8.6Hz,1H),7.63(dd,J=13.3,5.4Hz,2H),7.57-7.54(m,2H),7.48(t,J=7.6Hz,1H),7.24(t,J=7.4Hz,1H),4.43(t,J=6.9Hz,2H),1.81-1.75(m,2H),1.36-1.27(m,2H),0.90(t,J=7.5Hz,3H);HRESIMS m/z 561.1841[M-H]-,cacld C37H26N2O4for:562.1893。】
实施例6-2:IVb(0.40mmol,0.2g)、氰基乙酸(1.20mmol,0.1g)和吡啶(0.03g,0.4mmol)溶于体积比为1:1的氯仿和乙腈(6mL)中,氮气保护下加热回流6h。反应液冷至室温,直接旋干,柱层析(VCH2Cl2:VCH3OH:VHAc=400:4:1)分离得深红色固体0.13g,收率58%。实施例7:化合物(III)的合成
实施例7-1:IVc(0.05mmol,0.026g)、氰基乙酸(0.01mmol,0.11g)和哌啶(0.021mL,0.2mmol)溶于氯仿(1mL)中,氮气保护下加热回流12h,反应液冷至室温,直接旋干,柱层析(VCH2Cl2:VCH3OH:VHAc=400:4:1)分离得深红色固体0.02g,收率78%。m.p.261~263℃;1H NMR(500MHz,d-DMSO)δ:8.62(d,J=1.5Hz,1H),8.47(s,1H),8.31(d,J=7.7Hz,1H),8.09-8.03(m,2H),8.01(dd,J=4.6,3.0Hz,2H),7.96(d,J=1.4Hz,1H),7.93-7.90(m,2H),7.85(dd,J=8.8,1.8Hz,2H),7.67(d,J=8.6Hz,1H),7.62(d,J=8.4Hz,1H),7.48(t,J=7.6Hz,1H),7.24(t,J=7.4Hz,1H),4.42(t,J=6.9Hz,2H),1.82-1.75(m,2H),1.36-1.29(m,2H),0.90(t,J=7.4Hz,3H);HRESIMS m/z 577.1603[M-H]-,cacld C37H26N2O3S for:578.1664。
实施例7-2:IVc(0.05mmol,0.026g)、氰基乙酸(0.01mmol,0.11g)和三乙胺(0.015g,0.15mmol)溶于氯仿(2mL)中,氮气保护下加热回流8h,反应液冷至室温,直接旋干,柱层析(VCH2Cl2:VCH3OH:VHAc=400:4:1)分离得深红色固体0.015g,收率59%。
实施例8:咔唑类化合物作为染料敏化剂的应用
利用丝网印刷制备的TiO2纳米粒子膜作为光电极:首先在导电玻璃FTO上印一层12μm厚的20nm的TiO2粒子,450℃下马弗炉内煅烧30min。在浸染料之前将烧好的膜浸入0.04mol·L-1的TiCl4水溶液70℃预处理30min,然后分别用水和乙醇冲洗,电吹风吹干。经马弗炉450℃下再次煅烧30min后,冷却至80℃后浸入3×10-4mol·L-1染料的甲醇与氯仿溶液(VCH3OH:VCHCl3=1:10)室温24h敏化。对电极的制备:采用丝网印刷方法,将H2PtCl6溶液印刷在FTO导电玻璃上,然后400℃马弗炉烧结20min。吸附染料的TiO2电极和铂对电极组装成三明治结构,并在边缘滴入电解质(含0.07mM/LI-),利用毛细管渗透原理引入电池内部。于100mW/cm2光强照射下,测定光电压-电流特性曲线。其结果如表1所示:
表1咔唑类化合物组装得到的DSSC性能参数
从表1中可以看出三个化合物的光电转换效率为4.57-4.88%,π桥为苯环的染料敏化剂化合物I因其开路电压优于π桥为噻吩和呋喃环的染料敏化剂化合物II和化合物III,因而具有更高的光电转换效率。
Claims (10)
1.一种含芴酮的N-丁基咔唑类化合物,其特征在于包括如式(Ⅰ)、式(Ⅱ)及式(III)所示的化合物Ⅰ、化合物Ⅱ和化合物III:
2.根据权利要求1所述的一种含芴酮的N-丁基咔唑类化合物,其特征在于化合物Ⅰ、化合物Ⅱ和化合物III中电子受体为2-氰基丙烯酸。
3.一种根据权利要求1所述的含芴酮的N-丁基咔唑类化合物的制备方法,其特征在于包括如下步骤:在有机溶剂中,将式(IVa)、式(IVb)、式(IVc)所示的化合物IVa、化合物IVb、化合物IVc分别与式(V)所示的化合物V混合,在碱性化合物的作用下,加热回流搅拌反应1~10h,反应完全后,旋干溶剂,残余物用洗脱剂溶剂进行硅胶柱层析,获得式(I)、式(II)和式(III)所示的化合物Ⅰ、化合物Ⅱ和化合物III;
4.根据权利要求3所述的含芴酮的N-丁基咔唑类化合物的制备方法,其特征在于碱性化合物为哌啶、吡啶、三乙胺或者三甲胺中的一种或多种混合物。
5.根据权利要求3所述的含芴酮的N-丁基咔唑类化合物的制备方法,其特征在于有机溶剂为乙腈、氯仿、四氢呋喃或1,4-二氧六环中的一种或多种混合物。
6.根据权利要求3所述的含芴酮的N-丁基咔唑类化合物的制备方法,其特征在于洗脱剂溶剂为卤代甲烷、醇及醋酸的混合物,所述卤代甲烷为氯仿或二氯甲烷,所述醇为甲醇或乙醇,优选洗脱剂溶剂为体积比为400:4:1的二氯甲烷、甲醇和醋酸的混合溶剂。
7.根据权利要求3所述的含芴酮的N-丁基咔唑类化合物的制备方法,其特征在于式(IVa~IVc)化合物、式(V)化合物和碱性化合物的物质的量之比为1:1.0~3.0:1.0~4.0;有机溶剂体积用量以式(IVa~IVc)化合物的物质的量计为10~30mL/mmol,优选为15mL/mmol。
8.根据权利要求3所述的含芴酮的N-丁基咔唑类化合物的制备方法,其特征在于所述反应时间为8~12h,优选为12h。
9.根据权利要求1所述的含芴酮的N-丁基咔唑类化合物作为染料敏化剂在太阳能电池上的应用。
10.根据权利要求9所述的应用,其特征在于具体应用过程为:将含芴酮的N-丁基咔唑类化合物溶于体积比为1:10的CH3OH和CHCl3混合溶剂中,浸泡TiO2纳米粒子膜光电极24h,负载了含芴酮的N-丁基咔唑类化合物的TiO2电极与铂对电极组装成三明治结构,并在边缘滴入电解质,利用毛细管渗透原理引入电池内部,于100mW/cm2光强照射下,测定光电压-电流特性曲线,得含芴酮的N-丁基咔唑类化合物的光电转换效率为4.57-4.88%。
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