CN112552491A - 一种含3-己基噻吩的卟啉聚合物及其合成方法 - Google Patents
一种含3-己基噻吩的卟啉聚合物及其合成方法 Download PDFInfo
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- 150000004032 porphyrins Chemical class 0.000 title claims abstract description 40
- 229920000642 polymer Polymers 0.000 title claims abstract description 39
- JEDHEMYZURJGRQ-UHFFFAOYSA-N 3-hexylthiophene Chemical compound CCCCCCC=1C=CSC=1 JEDHEMYZURJGRQ-UHFFFAOYSA-N 0.000 title claims abstract description 16
- 238000010189 synthetic method Methods 0.000 title description 4
- 238000006243 chemical reaction Methods 0.000 claims abstract description 50
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract description 32
- 238000000034 method Methods 0.000 claims abstract description 20
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 14
- MNDIARAMWBIKFW-UHFFFAOYSA-N 1-bromohexane Chemical compound CCCCCCBr MNDIARAMWBIKFW-UHFFFAOYSA-N 0.000 claims abstract description 6
- PBTPREHATAFBEN-UHFFFAOYSA-N dipyrromethane Chemical compound C=1C=CNC=1CC1=CC=CN1 PBTPREHATAFBEN-UHFFFAOYSA-N 0.000 claims abstract description 6
- KCDXJAYRVLXPFO-UHFFFAOYSA-N syringaldehyde Chemical compound COC1=CC(C=O)=CC(OC)=C1O KCDXJAYRVLXPFO-UHFFFAOYSA-N 0.000 claims abstract description 6
- COBXDAOIDYGHGK-UHFFFAOYSA-N syringaldehyde Natural products COC1=CC=C(C=O)C(OC)=C1O COBXDAOIDYGHGK-UHFFFAOYSA-N 0.000 claims abstract description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 177
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 78
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 58
- 239000003208 petroleum Substances 0.000 claims description 40
- 239000000203 mixture Substances 0.000 claims description 33
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 30
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 27
- 229910052757 nitrogen Inorganic materials 0.000 claims description 27
- 238000001035 drying Methods 0.000 claims description 23
- 238000005406 washing Methods 0.000 claims description 22
- 238000003756 stirring Methods 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 14
- 230000002194 synthesizing effect Effects 0.000 claims description 14
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 13
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims description 12
- 239000003480 eluent Substances 0.000 claims description 12
- 239000012153 distilled water Substances 0.000 claims description 11
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 claims description 10
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 10
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 claims description 10
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 claims description 8
- 238000010828 elution Methods 0.000 claims description 8
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- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 claims description 8
- 229940126062 Compound A Drugs 0.000 claims description 7
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims description 7
- 238000002390 rotary evaporation Methods 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- 229910021595 Copper(I) iodide Inorganic materials 0.000 claims description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 6
- 239000012044 organic layer Substances 0.000 claims description 6
- 239000012074 organic phase Substances 0.000 claims description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 6
- 238000001291 vacuum drying Methods 0.000 claims description 6
- 238000004440 column chromatography Methods 0.000 claims description 5
- 238000011049 filling Methods 0.000 claims description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 5
- 238000010992 reflux Methods 0.000 claims description 5
- 229910001873 dinitrogen Inorganic materials 0.000 claims description 4
- 238000000605 extraction Methods 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 claims description 4
- NSYFIAVPXHGRSH-UHFFFAOYSA-N 2,5-dibromo-3-hexylthiophene Chemical compound CCCCCCC=1C=C(Br)SC=1Br NSYFIAVPXHGRSH-UHFFFAOYSA-N 0.000 claims description 3
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 claims description 3
- 238000006392 deoxygenation reaction Methods 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 3
- 238000010791 quenching Methods 0.000 claims description 3
- 230000000171 quenching effect Effects 0.000 claims description 3
- 238000007789 sealing Methods 0.000 claims description 3
- 238000000967 suction filtration Methods 0.000 claims description 3
- CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 2
- ZOUWOGOTHLRRLS-UHFFFAOYSA-N palladium;phosphane Chemical compound P.[Pd] ZOUWOGOTHLRRLS-UHFFFAOYSA-N 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 abstract description 13
- 238000003786 synthesis reaction Methods 0.000 abstract description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract description 10
- 239000006227 byproduct Substances 0.000 abstract description 5
- 239000013067 intermediate product Substances 0.000 abstract description 5
- 239000000463 material Substances 0.000 abstract description 5
- 239000003960 organic solvent Substances 0.000 abstract description 5
- 239000002994 raw material Substances 0.000 abstract description 5
- 238000012360 testing method Methods 0.000 abstract description 3
- -1 porphyrin compound Chemical class 0.000 abstract 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 abstract 2
- NOKFACHNZFXTGH-UHFFFAOYSA-N 4-hexoxy-3,5-dimethoxybenzaldehyde Chemical compound CCCCCCOC1=C(OC)C=C(C=O)C=C1OC NOKFACHNZFXTGH-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 238000001308 synthesis method Methods 0.000 abstract 1
- 238000000746 purification Methods 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 3
- 239000012043 crude product Substances 0.000 description 2
- 238000003760 magnetic stirring Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- YNHIGQDRGKUECZ-UHFFFAOYSA-N dichloropalladium;triphenylphosphanium Chemical compound Cl[Pd]Cl.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000005669 field effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
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Abstract
本发明公开了一种含3‑己基噻吩的卟啉聚合物及其合成方法,涉及太阳能电池材料领域,本发明设计合成了的一类新型的卟啉化合物,主要由吡咯合成的二吡咯甲烷以及丁香醛与1‑溴代正己烷生成的4‑己氧基‑3,5‑二甲氧基苯甲醛相互反应合成卟啉化合物,再通过上溴、配位等操作进一步修饰合成的卟啉化合物,再将该卟啉化合物与2,5‑二炔‑3‑己基噻吩聚合得到目标卟啉聚合物。本发明能够解决现有的卟啉聚合物合成时原料价格高昂、合成过程繁琐、合成条件苛刻。合成成本较高、中间产物收集率较低、副产物较多且占比较大以及在四氢呋喃和氯仿等有机溶剂中的溶解度较低导致测试光电转换效率较为不便的问题。
Description
技术领域
本发明涉及太阳能电池材料领域,尤其涉及一种含3-己基噻吩的卟啉聚合物及其合成方法。
背景技术
太阳能电池是近年来发展最迅猛、最具活力的研究热点之一。聚合物太阳电池因具有低成本的潜力、并且易于加工,可在柔性衬底上实现柔性器件制备等特点,正受科研以及工业界的广泛关注。卟啉类作为有机光敏基元中的一种,在有机太阳能电池构建中扮演着重要角色,在自然界中负责收集、捕获和传递太阳光能,同时具备化学稳定性和结构可调节性。
现有的卟啉聚合物作为有机太阳能电池中负责收集、捕获和传递太阳光能的材料主要有以下不足:
1.合成现有的卟啉聚合物所采用的原料价格高昂、合成过程繁琐、合成条件苛刻且合成成本较高。
2.合成现有的卟啉聚合物的过程中,中间产物收集率较低,副产物较多且占比较大。
3.现有的卟啉聚合物在四氢呋喃和氯仿等有机溶剂中的溶解度较低,测试光电转换效率较为不便。
发明内容
本发明所要解决的技术问题是提供一种含3-己基噻吩的卟啉聚合物及其合成方法,解决现有的卟啉聚合物合成时原料价格高昂、合成过程繁琐、合成条件苛刻。合成成本较高、中间产物收集率较低、副产物较多且占比较大以及在四氢呋喃和氯仿等有机溶剂中的溶解度较低导致测试光电转换效率较为不便的问题。
本发明解决其技术问题所采用的技术方案是:一种含3-己基噻吩的卟啉聚合物,结构如下:
本发明还提供了一种合成上述含3-己基噻吩的卟啉聚合物的方法,包括以下步骤:
(1)将丁香醛与1-溴代正己烷、无水K2CO3、NaI在二甲基甲酰胺中反应,充氮气保护下,电磁搅拌,加热,反应完成后加入蒸馏水洗涤,使用乙酸乙酯和石油醚萃取,再将有机层合并,加入无水硫酸镁干燥,使用二氯甲烷和石油醚为混合洗脱剂将其洗至纯化,得到化合物A;
(2)将二吡咯甲烷与化合物A、二氯甲烷、三氟乙酸在氮气保护下搅拌,加入二氯二氰基苯醌,继续搅拌,反应完成后,加入三乙胺碱化,减压真空旋干,使用二氯甲烷和石油醚为混合洗脱剂将其洗至纯化,得到化合物B;
(3)将化合物B溶于二氯甲烷,缓慢滴加溶于二氯甲烷中的N-溴代琥珀酰亚胺后在氮气保护下搅拌,反应完成后,加入丙酮淬灭,减压真空旋干,使用二氯甲烷和石油醚为混合洗脱剂将其洗至纯化,得到化合物C;
(4)将化合物C和Zn(OAc)·2H2O加入二氯甲烷和甲醇溶液中,在氮气保护下反应,反应完成后,加入蒸馏水洗涤,使用二氯甲烷萃取,将有机层合并后,加入无水硫酸镁干燥,减压真空旋干,使用二氯甲烷和石油醚为混合洗脱剂将其洗至纯化,得到化合物D;
(5)将2,5-二溴-3-己基噻吩溶于四氢呋喃中,加入无水三乙胺,反应容器中充入氮气脱氧,再加入碘化亚铜、双三苯基膦二氯化钯和三甲基硅基乙炔,反应后再充入氮气密封保存,在室温条件下磁力搅拌反应后旋蒸除去溶剂,再用饱和NaCl溶液洗涤,用CHCl2萃取,最后合并有机相,用无水硫酸钠干燥,旋转蒸发得混合物E,将混合物E用石油醚和乙酸乙酯洗脱至纯化,得到2,5-三甲基硅基二炔-3-己基噻吩,在2,5-三甲基硅基二炔-3-己基噻吩中加入四氢呋喃,再加入四丁基氟化铵,室温搅拌后加入蒸馏水,用二氯甲烷萃取,再用饱和NaCl溶液洗涤,合并有机相再加入无水硫酸钠,充分振荡后静置,抽滤、旋干得混合物F,将混合物F用二氯甲烷和石油醚洗脱至纯化,得到2,5-二炔-3-己基噻吩;
(6)将化合物4和2,5-二炔-3-己基噻吩加入反应容器,加入无水四氢呋喃和无水三乙胺,加入Pd(PPh3)2Cl2和CuI,通氮气排尽烧瓶中空气,回流反应,反应结束后,加入水,用二氯甲烷萃取,加入无水硫酸钠干燥,减压旋蒸除去溶剂,用二氯甲烷和石油醚柱层析,得到卟啉聚合物。
进一步地,所述步骤(1)中,丁香醛与1-溴代正己烷、无水K2CO3、NaI在二甲基甲酰胺的反应温度为85℃-90℃,反应时间为12h,蒸馏水洗涤后萃取时使用的乙酸乙酯和石油醚的体积比为1:1,加入无水硫酸镁干燥时间为30min,无水硫酸镁干燥后使用的二氯甲烷和石油醚的体积比为3:2。
进一步地,所述步骤(2)中,二吡咯甲烷与化合物A、二氯甲烷、三氟乙酸在氮气保护下的搅拌温度为23℃,搅拌时间为4h,加入二氯二氰基苯醌继续搅拌时间为1h,洗脱时使用的二氯甲烷和石油醚体积比为2:1。
进一步地,所述步骤(3)中,化合物B溶于二氯甲烷,缓慢滴加溶于二氯甲烷中的N-溴代琥珀酰亚胺后在0℃及氮气保护下搅拌6h,洗脱时使用的二氯甲烷和石油醚体积比为3:2。
进一步地,所述步骤(4)中,将化合物C加入二氯甲烷和甲醇溶液中,在23℃及氮气保护下反应3h,加入无水硫酸镁干燥时间为30min,洗脱时使用的二氯甲烷和石油醚体积比为5:2。
进一步地,所述步骤(5)中,反应容器中充入氮气脱氧时间为15min,反应后充入氮气15min后再密封保存,磁力搅拌时间为72h,加入无水硫酸钠干燥时间为30min,混合物E在VZ-purifier制备液相色谱仪中用体积比为30:1的石油醚和乙酸乙酯洗脱,在2,5-三甲基硅基二炔-3-己基噻吩中加入四氢呋喃,再加入四丁基氟化铵,室温搅拌时间为30min,充分振荡后静置时间为30min,混合物F在VZ-purifier制备液相色谱仪中用体积比为20:1的二氯甲烷和石油醚洗脱。
进一步地,所述步骤(6)中,回流反应的反应温度为70℃,反应时间为24h,加入无水硫酸钠干燥时间为30min,柱层析时使用的二氯甲烷和石油醚的体积比为3:2。
本发明还提供了一种上述卟啉聚合物的应用,将上述卟啉聚合物应用于太阳能电池用于收集、捕获和传递太阳光能。
本发明具有如下有益效果:
合成本发明的卟啉聚合物所采用的原料价格低廉、合成过程简单、合成条件简便易行且合成成本较低。
合成现有的卟啉聚合物的过程中,中间产物收集率较高,副产物较少且占比较小。
现有的卟啉聚合物在四氢呋喃和氯仿等有机溶剂中的溶解度较高,测试光电转换效率较为方便。
具体实施方式
实施例1:
按照以下步骤合成卟啉聚合物:
(1)将丁香醛(2.12g,0.0116mol),1-溴代正己烷(5.76g,0.035mol),无水K2CO3(2.04g,0.015mol),NaI(0.05g,0.006mol)在20mlDMF中反应,充氮气保护下,电磁搅拌,加热至85℃-90℃,反应12小时。反应完成后,加入3×20ml的蒸馏水洗涤,使用3×30ml乙酸乙酯/石油醚(V1:V2=1:1)萃取,再将有机层合并,加入无水硫酸镁进行30min干燥。然后以二氯甲烷/石油醚(V1:V2=3:2)为混合洗脱剂将其洗至纯化,得到化合物A2.32g,产率89%。
化合物A结构式如下:
(2)将二吡咯甲烷(1.05g,7.19mmol)和化合物A(1.91g,7.19mmol)在0.5L二氯甲烷的溶液,加入三氟乙酸(0.48l,7.44mol),在23℃下,氮气保护下搅拌4h,加入DDQ(2.88g,12.24mmol),并将混合物再搅拌1h。反应完成后,加入三乙胺(1.4ml)碱化,减压真空旋干。然后以二氯甲烷/石油醚(V1:V2=2:1)为混合洗脱剂将其洗至纯化,得到化合物B0.75g,产率28%。
化合物B结构式如下:
(3)将化合物B(0.5g,0.640mmol)溶于300ml二氯甲烷的溶液中,缓慢滴加溶于120ml二氯甲烷中的NBS(0.22,12.8mmol)后在0℃氮气保护下搅拌6h。反应完成后,加入10ml丙酮淬灭,减压真空旋干。然后以二氯甲烷/石油醚(V1:V2=3:2)为混合洗脱剂将其洗至纯化,得到化合物C0.38g,产率56%。
化合物C结构式如下:
(4)化合物C(0.30g,0.319mmol)和Zn(OAc)·2H2O(0.700g,3.19mmol)加入65ml二氯甲烷和32ml甲醇溶液中,在23℃下,氮气保护下反应3h,反应完成后,加入2×30ml的蒸馏水洗涤,使用2×30ml二氯甲烷进行萃取,将有机层合并后,加入无水硫酸镁干燥30min。减压真空旋干。以二氯甲烷/石油醚(V1:V2=5:2)为混合洗脱剂将其洗至纯化,得到化合物D0.19g,产率37%。
化合物D结构式如下:
(5)称取2,5-二溴-3-己基噻吩0.3260g(1mmol)溶于20mlTHF在150ml二通圆底烧瓶中,然后加入10mL的无水三乙胺。反应容器中充入氮气15min,进行脱氧。此外,再加入10mg(0.05mmol)碘化亚铜、35mg(0.05mmol)双三苯基膦二氯化钯和三甲基硅基乙炔0.4g(5mmol)。反应再充入氮气15min,进行密封保存,在室温条件下磁力搅拌反应72h后旋蒸除去溶剂,接着用饱和的NaCl溶液洗涤三次,每次8.0mL,然后用CHCl2萃取三次,每次5.0mL,最后合并有机相,用适量无水硫酸钠干燥30分钟后,旋转蒸发得0.2987g深黄色油状粗品混合物E,在VZ-purifier制备液相色谱仪中用石油醚和乙酸乙酯(V:V=30:1)洗脱液淋洗纯化,得到淡黄色黏稠状液体2,5-三甲基硅基二炔-3-己基噻吩0.2282g,产率为70.0%。然后在50ml圆底烧瓶中称取0.200g(0.6097mmol)上述产物,加入50ml的THF,再加入四丁基氟化铵(0.5g,75%in water)。室温搅拌30min后,向反应瓶中加入50ml蒸馏水,接着用二氯甲烷萃取三次,每次用量为10.0ml,再用饱和的NaCl溶液洗涤三次,每次用量为10.0mL,合并有机相再加入适量的无水硫酸钠,在充分振荡后静置30分钟,抽滤、旋干得0.1647g黏稠状粗品混合物F。在VZ-purifier制备液相色谱仪中用展开剂二氯甲烷和石油醚(V:V=1:20)洗脱液淋洗纯化,得到黄色黏稠状液体2,5-二炔-3-己基噻吩0.1224g,产率为61.2%。
(6)将化合物D(100mg0.0996mmol)和2,5-二炔-3-己基噻吩(37.5mg0.0996mmol)加入到圆底烧瓶中,加入10ml无水四氢呋喃和5ml无水三乙胺,加入Pd(PPh3)2Cl2(13.75mg0.02mmol)和CuI(5.87mg0.03mmol),通氮气排尽烧瓶中空气,反应体系在70℃下回流反应24h,反应结束后,加入30ml水然后用二氯甲烷萃取几次,加入无水硫酸钠干燥30min,减压旋蒸除去溶剂,用二氯甲烷:石油醚=3:2(体积比)手动柱层析,得到产物卟啉聚合物50mg。
合成本发明的卟啉聚合物所采用的原料价格低廉、合成过程简单、合成条件简便易行且合成成本较低。
合成现有的卟啉聚合物的过程中,中间产物收集率较高,副产物较少且占比较小。
现有的卟啉聚合物在四氢呋喃和氯仿等有机溶剂中的溶解度较高,测试光电转换效率较为方便。
该卟啉聚合物具有高的结晶性和在薄膜下形成好的π-π作用,因此基于该聚合物的器件表现出较好的场效应迁移率。将其应用到电池器件中,初步研究了器件性能,获得了约2.08%的光电转换效率。尽管该含卟啉低聚物的光电效率偏低,但是其在长波长方向具有更强且宽的光谱吸收,这为设计高效太阳电池材料提供了新的设计思路。
以上所述,仅是本发明的较佳实施例而已,并非对本发明作任何形式上的限制,任何熟悉本专业的技术人员,在不脱离本发明技术方案范围内,当可利用上述揭示的技术内容做出些许更动或修饰为等同变化的等效实施例,但凡是未脱离本发明技术方案内容,依据本发明的技术实质,在本发明的精神和原则之内,对以上实施例所作的任何简单的修改、等同替换与改进等,均仍属于本发明技术方案的保护范围之内。
Claims (9)
2.一种合成如权利要求1所述的含3-己基噻吩的卟啉聚合物的方法,其特征在于,包括以下步骤:
(1)将丁香醛与1-溴代正己烷、无水K2CO3、NaI在二甲基甲酰胺中反应,充氮气保护下,电磁搅拌,加热,反应完成后加入蒸馏水洗涤,使用乙酸乙酯和石油醚萃取,再将有机层合并,加入无水硫酸镁干燥,使用二氯甲烷和石油醚为混合洗脱剂将其洗至纯化,得到化合物A;
(2)将二吡咯甲烷与化合物A、二氯甲烷、三氟乙酸在氮气保护下搅拌,加入二氯二氰基苯醌,继续搅拌,反应完成后,加入三乙胺碱化,减压真空旋干,使用二氯甲烷和石油醚为混合洗脱剂将其洗至纯化,得到化合物B;
(3)将化合物B溶于二氯甲烷,缓慢滴加溶于二氯甲烷中的N-溴代琥珀酰亚胺后在氮气保护下搅拌,反应完成后,加入丙酮淬灭,减压真空旋干,使用二氯甲烷和石油醚为混合洗脱剂将其洗至纯化,得到化合物C;
(4)将化合物C和Zn(OAc)·2H2O加入二氯甲烷和甲醇溶液中,在氮气保护下反应,反应完成后,加入蒸馏水洗涤,使用二氯甲烷萃取,将有机层合并后,加入无水硫酸镁干燥,减压真空旋干,使用二氯甲烷和石油醚为混合洗脱剂将其洗至纯化,得到化合物D;
(5)将2,5-二溴-3-己基噻吩溶于四氢呋喃中,加入无水三乙胺,反应容器中充入氮气脱氧,再加入碘化亚铜、双三苯基膦二氯化钯和三甲基硅基乙炔,反应后再充入氮气密封保存,在室温条件下磁力搅拌反应后旋蒸除去溶剂,再用饱和NaCl溶液洗涤,用CHCl2萃取,最后合并有机相,用无水硫酸钠干燥,旋转蒸发得混合物E,将混合物E用石油醚和乙酸乙酯洗脱至纯化,得到2,5-三甲基硅基二炔-3-己基噻吩,在2,5-三甲基硅基二炔-3-己基噻吩中加入四氢呋喃,再加入四丁基氟化铵,室温搅拌后加入蒸馏水,用二氯甲烷萃取,再用饱和NaCl溶液洗涤,合并有机相再加入无水硫酸钠,充分振荡后静置,抽滤、旋干得混合物F,将混合物F用二氯甲烷和石油醚洗脱至纯化,得到2,5-二炔-3-己基噻吩;
(6)将化合物4和2,5-二炔-3-己基噻吩加入反应容器,加入无水四氢呋喃和无水三乙胺,加入Pd(PPh3)2Cl2和CuI,通氮气排尽烧瓶中空气,回流反应,反应结束后,加入水,用二氯甲烷萃取,加入无水硫酸钠干燥,减压旋蒸除去溶剂,用二氯甲烷和石油醚柱层析,得到卟啉聚合物。
3.如权利要求2所述的一种合成含3-己基噻吩的卟啉聚合物的方法,其特征在于,所述步骤(1)中,丁香醛与1-溴代正己烷、无水K2CO3、NaI在二甲基甲酰胺的反应温度为85℃-90℃,反应时间为12h,蒸馏水洗涤后萃取时使用的乙酸乙酯和石油醚的体积比为1:1,加入无水硫酸镁干燥时间为30min,无水硫酸镁干燥后使用的二氯甲烷和石油醚的体积比为3:2。
4.如权利要求2所述的一种合成含3-己基噻吩的卟啉聚合物的方法,其特征在于,所述步骤(2)中,二吡咯甲烷与化合物A、二氯甲烷、三氟乙酸在氮气保护下的搅拌温度为23℃,搅拌时间为4h,加入二氯二氰基苯醌继续搅拌时间为1h,洗脱时使用的二氯甲烷和石油醚体积比为2:1。
5.如权利要求2所述的一种合成含3-己基噻吩的卟啉聚合物的方法,其特征在于,所述步骤(3)中,化合物B溶于二氯甲烷,缓慢滴加溶于二氯甲烷中的N-溴代琥珀酰亚胺后在0℃及氮气保护下搅拌6h,洗脱时使用的二氯甲烷和石油醚体积比为3:2。
6.如权利要求2所述的一种合成含3-己基噻吩的卟啉聚合物的方法,其特征在于,所述步骤(4)中,将化合物C加入二氯甲烷和甲醇溶液中,在23℃及氮气保护下反应3h,加入无水硫酸镁干燥时间为30min,洗脱时使用的二氯甲烷和石油醚体积比为5:2。
7.如权利要求2所述的一种合成含3-己基噻吩的卟啉聚合物的方法,其特征在于,所述步骤(5)中,反应容器中充入氮气脱氧时间为15min,反应后充入氮气15min后再密封保存,磁力搅拌时间为72h,加入无水硫酸钠干燥时间为30min,混合物E在VZ-purifier制备液相色谱仪中用体积比为30:1的石油醚和乙酸乙酯洗脱,在2,5-三甲基硅基二炔-3-己基噻吩中加入四氢呋喃,再加入四丁基氟化铵,室温搅拌时间为30min,充分振荡后静置时间为30min,混合物F在VZ-purifier制备液相色谱仪中用体积比为20:1的二氯甲烷和石油醚洗脱。
8.如权利要求2所述的一种合成含3-己基噻吩的卟啉聚合物的方法,其特征在于,所述步骤(6)中,回流反应的反应温度为70℃,反应时间为24h,加入无水硫酸钠干燥时间为30min,柱层析时使用的二氯甲烷和石油醚的体积比为3:2。
9.一种卟啉聚合物的应用,其特征在于,将权利要求1所述的一种含3-己基噻吩的卟啉聚合物应用于太阳能电池用于收集、捕获和传递太阳光能。
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