CN114773580A - 非规整三元共轭聚合物光催化材料及其制备方法和应用 - Google Patents
非规整三元共轭聚合物光催化材料及其制备方法和应用 Download PDFInfo
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- CN114773580A CN114773580A CN202210471959.8A CN202210471959A CN114773580A CN 114773580 A CN114773580 A CN 114773580A CN 202210471959 A CN202210471959 A CN 202210471959A CN 114773580 A CN114773580 A CN 114773580A
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- photocatalytic material
- conjugated polymer
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- ternary
- palladium
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- 239000000463 material Substances 0.000 title claims abstract description 36
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- 238000013086 organic photovoltaic Methods 0.000 claims abstract description 6
- 238000007146 photocatalysis Methods 0.000 claims abstract description 6
- 238000007334 copolymerization reaction Methods 0.000 claims abstract description 3
- MLCPSWPIYHDOKG-BUHFOSPRSA-N (3e)-3-(2-oxo-1h-indol-3-ylidene)-1h-indol-2-one Chemical compound O=C\1NC2=CC=CC=C2C/1=C1/C2=CC=CC=C2NC1=O MLCPSWPIYHDOKG-BUHFOSPRSA-N 0.000 claims description 16
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 13
- 239000003054 catalyst Substances 0.000 claims description 13
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 12
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- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical compound C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 claims description 6
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- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 6
- YJSKZIATOGOJEB-UHFFFAOYSA-N thieno[2,3-b]pyrazine Chemical compound C1=CN=C2SC=CC2=N1 YJSKZIATOGOJEB-UHFFFAOYSA-N 0.000 claims description 6
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 claims description 5
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- UJWIUSHPLMZHFI-UHFFFAOYSA-N naphthalene-1,2-diimine Chemical compound C1=CC=C2C(=N)C(=N)C=CC2=C1 UJWIUSHPLMZHFI-UHFFFAOYSA-N 0.000 claims description 5
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- UDGKZGLPXCRRAM-UHFFFAOYSA-N 1,2,5-thiadiazole Chemical compound C=1C=NSN=1 UDGKZGLPXCRRAM-UHFFFAOYSA-N 0.000 claims description 3
- LFUIYIDCSSWXMG-UHFFFAOYSA-N 1,2-diphenylphenazine Chemical compound C1(=CC=CC=C1)C1=C(C2=NC3=CC=CC=C3N=C2C=C1)C1=CC=CC=C1 LFUIYIDCSSWXMG-UHFFFAOYSA-N 0.000 claims description 3
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 3
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 3
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- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 3
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- YEYHFKBVNARCNE-UHFFFAOYSA-N pyrido[2,3-b]pyrazine Chemical compound N1=CC=NC2=CC=CN=C21 YEYHFKBVNARCNE-UHFFFAOYSA-N 0.000 claims description 3
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical compound C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 claims description 3
- MABNMNVCOAICNO-UHFFFAOYSA-N selenophene Chemical compound C=1C=C[se]C=1 MABNMNVCOAICNO-UHFFFAOYSA-N 0.000 claims description 3
- 229930192474 thiophene Natural products 0.000 claims description 3
- KXSFECAJUBPPFE-UHFFFAOYSA-N 2,2':5',2''-terthiophene Chemical compound C1=CSC(C=2SC(=CC=2)C=2SC=CC=2)=C1 KXSFECAJUBPPFE-UHFFFAOYSA-N 0.000 claims description 2
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 229920006027 ternary co-polymer Polymers 0.000 claims description 2
- UMHFSEWKWORSLP-UHFFFAOYSA-N thiophene 1,1-dioxide Chemical compound O=S1(=O)C=CC=C1 UMHFSEWKWORSLP-UHFFFAOYSA-N 0.000 claims description 2
- 150000003606 tin compounds Chemical class 0.000 claims description 2
- HKNRNTYTYUWGLN-UHFFFAOYSA-N dithieno[3,2-a:2',3'-d]thiophene Chemical compound C1=CSC2=C1SC1=C2C=CS1 HKNRNTYTYUWGLN-UHFFFAOYSA-N 0.000 claims 1
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Abstract
本发明属于多功能光电应用的聚合物材料技术领域，目前已有的聚合物仍存在可见光利用率低、光生电子和空穴的复合率高等问题；本发明提供了一种非规整三元共轭聚合物光催化材料及其制备方法和应用，通过改变构成该类聚合物光催化材料的单体种类、调控单体投料的摩尔比，以无规则共聚的方式将不同π桥接单元引入聚合物材料的基本骨架中，调控最高占据轨道和最低占据轨道能级，增强分子链间π‑π相互作用力，拓宽和增强光吸收并提升了电荷传输能力，从而提升光催化性能。该材料具有良好的热稳定性和匹配的能级，且材料合成步骤简单，可广泛用于光催化、钙钛矿太阳能电池、有机场效应晶体管、有机电致发光器件和有机光伏太阳能电池领域。
Description
技术领域
本发明属于多功能光电应用的聚合物材料技术领域，特别是一种非规整三元共轭聚合物光催化材料及其制备方法和应用。
背景技术
能源是人类不可或缺的物质基础，随着经济和科技的快速发展，不可再生化石燃料引起的环境污染和能源危机问题引起了全球的关注，迫切需要可替代的绿色清洁能源。利用太阳能催化析氢是简单有效的方法，氢能能量密度高且无污染、可存储，有望替代传统的化石能源(J.Colloid Interface Sci.2019,533,636-648)。
光催化析氢的活性高低在于半导体光催化剂材料的选取，有机聚合物光催化剂因其结构易于设计、合成方法多且性质易调节而受到广泛的关注(Chem.Rev.2020,120,2171)。其中，供体-受体型(D-A)聚合物通过选择不同的富电子和缺电子基团对结构进行修饰，不仅能够调控分子轨道的能级和分子间的相互作用，而且能够改变聚合物的共轭体系和微观分子结构的平整度。然而目前已有的聚合物仍存在可见光利用率低、光生电子和空穴的复合率高等问题(J.Mater.Chem.A 2019,7,8938-8951；Appl.Catal.B 2019,257,117935)。因此，需要进一步开发一种能够实现能级匹配、可见光利用率高的聚合物光催化材料。
发明内容
针对现有技术存在的不足，本发明的目的在于提供一种非规整三元共轭聚合物光催化材料及其制备方法和应用，该材料具有匹配的能级、较好的热稳定性和优异的光吸收性能，且易于制备、适用于大规模应用，能够广泛应用于光催化、钙钛矿太阳能电池、有机场效应晶体管、有机电致发光器件和有机光伏太阳能电池等领域。
本发明的目的是通过以下技术方案来解决的：
一种非规整三元共轭聚合物光催化材料，非规整三元共轭聚合物光催化材料含有非规整三元共聚结构，具有以下的分子结构式：
上述分子式中，A、B为苯并二噻吩(BDT)、苯并噻二唑(BT)、苯并噁二唑(BO)、苯并二噻吩二酮(BDD)、苯并三噻吩(BTT)、二噻吩二酰亚胺(BTI)、双吡啶并[2,1,3]噻二唑(BPT)、二噻吩硅(DTS)、二噻吩苯并噻二唑(DTBT)、吡咯并吡咯二酮(DPP)、吡咯并二噻吩(DTP)、异靛(IID)、对称引达省并噻吩(IDT)、萘二亚胺(NDI)、芘咔唑(PC)、吡啶并吡嗪(PP)、二苯吩嗪(PPz)、二萘嵌苯(PDI)、喹喔啉(QU)、苯并三唑(TAZ)、噻吩吡咯二酮(TPD)、噻重氮异吲哚二酮(TID)、噻吩并吡嗪(TP)、咔唑、芴或环戊二噻吩中的其中一种单体，A、B的侧链结构为烷基链、烷氧基链或噻吩链的其中一种；π为桥接单元，桥接单元为低聚噻吩基、呋喃、芳香基、硒吩、吡啶、噻唑及其卤取代物和衍生物的其中一种；x、y为构成聚合物的单体与π桥接单元的投料摩尔比，满足x+y＝1且x>0，y>0。
进一步，π桥接单元中的低聚噻吩基为噻吩、联噻吩、三联噻吩、并二噻吩、二噻吩并噻吩或环戊二噻吩。
进一步，π桥接单元中的芳香基为苯、联苯、三联苯、萘或蒽。
一种如上述的非规整三元共轭聚合物光催化材料的制备方法，具体如下：
氮气氛围下，A、B单体与桥接单元π按照不同的投料摩尔比在催化剂的作用下通过无规共聚的方式合成非规整三元共轭聚合物光催化材料；根据所选A、B单体与桥接单元，通过卤代芳烃与有机锡化合物或有机硼酸酯化物的Stille交叉偶联反应合成非规整三元共轭聚合物光催化材料。
进一步，Stille交叉偶联反应的催化剂为钯(Ⅱ)或钯(0)催化剂。
进一步，Stille交叉偶联反应的催化剂为四三苯基膦钯、双(二亚芐基丙酮)钯、三(二亚苄基丙酮)二钯、醋酸钯或者双三苯基磷二氯化钯。
一种如上述方法制备而成的非规整三元共轭聚合物光催化材料在光催化、钙钛矿太阳能电池、有机场效应晶体管、有机电致发光器件和有机光伏太阳能电池领域的应用。
本发明具有以下有益效果：
本发明通过改变构成该类聚合物光催化材料的单体种类、调控单体投料的摩尔比，以无规则共聚的方式将不同π桥接单元引入聚合物材料的基本骨架中，调控最高占据轨道和最低占据轨道能级，增强分子链间π-π相互作用力，拓宽和增强光吸收并提升了电荷传输能力，从而提升光催化性能。该材料具有良好的热稳定性和匹配的能级，具有较好的热稳定性，有利于加工并延长使用寿命；且材料合成步骤简单，适用于大规模生产和应用，聚合物材料经过光学、电化学和电荷迁移率的测试表征，可广泛用于光催化、钙钛矿太阳能电池、有机场效应晶体管、有机电致发光器件和有机光伏太阳能电池领域。
附图说明
图1为本发明的结构图。
图2为本发明的聚合物材料1中的DI1在氯仿溶液中的循环伏安曲线图。
图3为本发明的聚合物材料1中的DI1与氮化碳(g-C3N4)和复合材料DI1/g-C3N4在氯仿溶液中的光吸收对比图。
图4为本发明的聚合物材料1中的DI1与g-C3N4按不同质量比合成样品的光催化分解水产氢速率(HER)对比图。
图5为本发明的聚合物材料1中的DI1与g-C3N4按不同质量比合成样品的阻抗对比图。
具体实施方式
下面结合附图对本发明作进一步详细说明。
如图1～5所示，本发明公开了一种非规整三元共轭聚合物光催化材料，聚合物光催化材料具有以下分子结构式：
上述分子式中，A、B为苯并二噻吩(BDT)、苯并噻二唑(BT)、苯并噁二唑(BO)、苯并二噻吩二酮(BDD)、苯并三噻吩(BTT)、二噻吩二酰亚胺(BTI)、双吡啶并[2,1,3]噻二唑(BPT)、二噻吩硅(DTS)、二噻吩苯并噻二唑(DTBT)、吡咯并吡咯二酮(DPP)、吡咯并二噻吩(DTP)、异靛(IID)、对称引达省并噻吩(IDT)、萘二亚胺(NDI)、芘咔唑(PC)、吡啶并吡嗪(PP)、二苯吩嗪(PPz)、二萘嵌苯(PDI)、喹喔啉(QU)、苯并三唑(TAZ)、噻吩吡咯二酮(TPD)、噻重氮异吲哚二酮(TID)、噻吩并吡嗪(TP)、咔唑、芴或环戊二噻吩中的其中一种单体，A、B的侧链结构为烷基链、烷氧基链或噻吩链的其中一种；π为桥接单元，具体为低聚噻吩基(如噻吩、联噻吩、三联噻吩、并二噻吩、二噻吩并噻吩或环戊二噻吩)、呋喃、芳香基(如苯、联苯、三联苯、萘或蒽)、硒吩、吡啶、噻唑及其卤取代物和衍生物的其中一种；x、y为构成聚合物的单体与π桥接单元的投料摩尔比，满足x+y＝1且x>0，y>0。
本发明还公开了一种上述的一种非规整三元共轭聚合物光催化材料的制备方法，通过以下反应聚合得到一种非规整三元共轭聚合物光催化材料，具体包括以下步骤：
氮气氛围下，A、B单体与π桥接单元按照不同的投料摩尔比在催化剂的作用下通过无规共聚的方式合成一种非规整三元共轭聚合物光催化材料，投料摩尔比只要满足三种单元和为1，比例可任取，即满足x+y＝1且x>0，y>0。根据所选单体A、B与桥接单元的不同组合，一般为卤代芳烃与有机锡化合物或有机硼酸酯化物的Stille交叉偶联反应。所选单体不同只对反应温度和钯催化剂的选择有影响。
Stille交叉偶联反应的催化剂为钯(Ⅱ)或钯(0)催化剂，如四三苯基膦钯、双(二亚芐基丙酮)钯、三(二亚苄基丙酮)二钯、醋酸钯或者双三苯基磷二氯化钯。
一种通过上述方法制备而成非规整三元共轭聚合物光催化材料经过光学、电化学和电荷迁移率的测试表征，具有能级匹配、光吸收性能好和电荷迁移率高的特点，在光催化、钙钛矿太阳能电池、有机场效应晶体管、有机电致发光器件和有机光伏太阳能电池领域广泛应用。
以下对本发明的原理和特征进行描述，所举实例只用于解释本发明，并非用于限定本发明的范围。
实施例1：
一种非规整三元共轭聚合物光催化材料DIn(n＝1、2、3)的合成：
如上所示，合成DIn(n＝1、2、3)当n取值不同时，x和y的配比分别是：
DI1 x:y＝1:3
DI2 x:y＝2:2
DI3 x:y＝3:1
合成步骤如下：
(1)DI1的合成
在两口烧瓶中将6,6'-二溴-1,1'-双(2-己基癸基)异靛(287.40mg，0.331mmol)，3,6-双(5-溴-2-噻吩基)-2,5-双(2-己基癸基)吡咯并[3,4-c]吡咯-1,4(2H,5H)-二酮(100mg，0.110mmol)，(3,3'-二氟-[2,2'-联噻吩]-5,5'-二基)双(三甲基锡烷)(232.79mg，0.441mmol)，三(二亚苄基丙酮)二钯(40.38mg，0.044mmol)混合。在氮气气氛下，向烧瓶中加入25mL无水氯苯，将反应混合物在130℃下加热回流48h。冷却至室温后，将混合物倒入甲醇中。过滤收集沉淀物，然后依次用己烷、丙酮、甲醇和氯仿进行索氏提取，提纯后产物即为DI1。
(2)DI2的合成
在两口烧瓶中将6,6'-二溴-1,1'-双(2-己基癸基)异靛(200mg，0.221mmol)，3,6-双(5-溴-2-噻吩基)-2,5-双(2-己基癸基)吡咯并[3,4-c]吡咯-1,4(2H,5H)-二酮(200mg，0.230mmol)，(3,3'-二氟-[2,2'-联噻吩]-5,5'-二基)双(三甲基锡烷)(486.00mg，0.921mmol)，三(二亚苄基丙酮)二钯(84.33mg，0.092mmol)混合。在氮气气氛下，向烧瓶中加入25mL无水氯苯，将反应混合物在130℃下加热回流48h。冷却至室温后，将混合物倒入甲醇中。过滤收集沉淀物，然后依次用己烷、丙酮、甲醇和氯仿进行索氏提取，提纯后产物即为DI2。
(3)DI3的合成
同DI1、DI2制备方法，原料如下：6,6'-二溴-1,1'-双(2-己基癸基)异靛(100.00mg,0.11mmol)，3,6-双(5-溴-2-噻吩基)-2,5-双(2-己基癸基)吡咯并[3,4-c]吡咯-1,4(2H,5H)-二酮(300.00mg,0.33mmol)，(3,3'-二氟-[2,2'-联噻吩]-5,5'-二基)双(三甲基锡烷)(232.79mg,0.44mmol)，产物即为DI3。
实施例2：
对实例1所合成的非规整三元聚合物材料中的DI1进行光学和电化学性能测试，并与g-C3N4制成Ⅰ型异质结应用于光催化制氢领域。
合成步骤：
首先将制备的g-C3N4与DI1以质量比为0wt％、0.5wt％、1wt％、2wt％、3wt％、4wt％超声分散于20mL氯仿溶液中，时长为1h，然后在室温下剧烈搅拌过夜。混合的溶液在旋转蒸发器上蒸发至干燥。最后，将混合样品过滤干燥，收集产物。
结果显示：在g-C3N4/DI1异质结中，当DI1质量比取2wt％时，光催化析氢速率可达到16000μmol g-1h-1。表明非规整三元共轭聚合物光催化材料DI1与氮化碳能级匹配，且互补的光吸收提高了对可见光的利用率，促进了电荷产生、分离和转移。
以上所述仅是本发明的优选实施方式，本发明的保护范围并不仅局限于上述实施例，凡属于本发明思路下的技术方案均属于本发明的保护范围。应当指出，对于本技术领域的普通技术人员来说，在不脱离本发明原理前提下的若干改进和润饰，这些改进和润饰也应视为本发明的保护范围。
Claims (7)
1.一种非规整三元共轭聚合物光催化材料，其特征在于，所述非规整三元共轭聚合物光催化材料含有非规整三元共聚结构，具有以下的分子结构式：
上述分子式中，A、B为苯并二噻吩(BDT)、苯并噻二唑(BT)、苯并噁二唑(BO)、苯并二噻吩二酮(BDD)、苯并三噻吩(BTT)、二噻吩二酰亚胺(BTI)、双吡啶并[2,1,3]噻二唑(BPT)、二噻吩硅(DTS)、二噻吩苯并噻二唑(DTBT)、吡咯并吡咯二酮(DPP)、吡咯并二噻吩(DTP)、异靛(IID)、对称引达省并噻吩(IDT)、萘二亚胺(NDI)、芘咔唑(PC)、吡啶并吡嗪(PP)、二苯吩嗪(PPz)、二萘嵌苯(PDI)、喹喔啉(QU)、苯并三唑(TAZ)、噻吩吡咯二酮(TPD)、噻重氮异吲哚二酮(TID)、噻吩并吡嗪(TP)、咔唑、芴或环戊二噻吩中的其中一种单体，A、B的侧链结构为烷基链、烷氧基链或噻吩链的其中一种；π为桥接单元，桥接单元为低聚噻吩基、呋喃、芳香基、硒吩、吡啶、噻唑及其卤取代物和衍生物的其中一种；x、y为构成聚合物的单体与π桥接单元的投料摩尔比，满足x+y＝1且x>0，y>0。
2.根据权利要求1所述的非规整三元共轭聚合物光催化材料，其特征在于，所述π桥接单元中的低聚噻吩基为噻吩、联噻吩、三联噻吩、并二噻吩、二噻吩并噻吩或环戊二噻吩。
3.根据权利要求1所述的非规整三元共轭聚合物光催化材料，其特征在于，所述π桥接单元中的芳香基为苯、联苯、三联苯、萘或蒽。
4.一种如权利要求1～3中任一权利要求所述的非规整三元共轭聚合物光催化材料的制备方法，其特征在于，具体如下：
氮气氛围下，A、B单体与桥接单元π按照不同的投料摩尔比在催化剂的作用下通过无规共聚的方式合成非规整三元共轭聚合物光催化材料；
根据所选A、B单体与桥接单元的不同，通过卤代芳烃与有机锡化合物或有机硼酸酯化物的Stille交叉偶联反应合成非规整三元共轭聚合物光催化材料。
5.根据权利要求4所述的非规整三元共轭聚合物光催化材料的制备方法，其特征在于，所述Stille交叉偶联反应的催化剂为钯(Ⅱ)或钯(0)催化剂。
6.根据权利要求5所述的非规整三元共轭聚合物光催化材料的制备方法，其特征在于，所述Stille交叉偶联反应的催化剂为四三苯基膦钯、双(二亚芐基丙酮)钯、三(二亚苄基丙酮)二钯、醋酸钯或者双三苯基磷二氯化钯。
7.一种如权利要求4～6中任一权利要求所述制备方法制备的非规整三元共轭聚合物光催化材料在光催化、钙钛矿太阳能电池、有机场效应晶体管、有机电致发光器件和有机光伏太阳能电池领域的应用。
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