CN110606939B - 聚（n,n-二苯基-4-（2,5-二甲基-1h-吡咯-1-基）苯胺）的应用及制备 - Google Patents
聚（n,n-二苯基-4-（2,5-二甲基-1h-吡咯-1-基）苯胺）的应用及制备 Download PDFInfo
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- CN110606939B CN110606939B CN201910653201.4A CN201910653201A CN110606939B CN 110606939 B CN110606939 B CN 110606939B CN 201910653201 A CN201910653201 A CN 201910653201A CN 110606939 B CN110606939 B CN 110606939B
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- diphenyl
- dimethyl
- aniline
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- electrode
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- ZNQIDANSWLUTDI-UHFFFAOYSA-N 4-(2,5-dimethylpyrrol-1-yl)-N,N-diphenylaniline Chemical compound C1(=CC=CC=C1)N(C1=CC=C(C=C1)N1C(=CC=C1C)C)C1=CC=CC=C1 ZNQIDANSWLUTDI-UHFFFAOYSA-N 0.000 title claims abstract description 48
- 238000002360 preparation method Methods 0.000 title claims description 8
- 239000000463 material Substances 0.000 claims abstract description 24
- 238000000034 method Methods 0.000 claims abstract description 20
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 15
- 239000000178 monomer Substances 0.000 claims description 12
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
- 239000003115 supporting electrolyte Substances 0.000 claims description 9
- -1 tetrafluoroborate Chemical compound 0.000 claims description 8
- 229920006254 polymer film Polymers 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- GTKRFUAGOKINCA-UHFFFAOYSA-M chlorosilver;silver Chemical compound [Ag].[Ag]Cl GTKRFUAGOKINCA-UHFFFAOYSA-M 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 6
- 229910052697 platinum Inorganic materials 0.000 claims description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 4
- 150000001450 anions Chemical class 0.000 claims description 4
- 150000001768 cations Chemical class 0.000 claims description 4
- 238000002484 cyclic voltammetry Methods 0.000 claims description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 claims description 4
- 229910001220 stainless steel Inorganic materials 0.000 claims description 4
- 239000010935 stainless steel Substances 0.000 claims description 4
- 239000010936 titanium Substances 0.000 claims description 4
- 229910052719 titanium Inorganic materials 0.000 claims description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 claims description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims description 2
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 claims description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
- 229910002651 NO3 Inorganic materials 0.000 claims description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 2
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 claims description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 2
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- ZOMNIUBKTOKEHS-UHFFFAOYSA-L dimercury dichloride Chemical class Cl[Hg][Hg]Cl ZOMNIUBKTOKEHS-UHFFFAOYSA-L 0.000 claims description 2
- 238000004070 electrodeposition Methods 0.000 claims description 2
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- 235000019253 formic acid Nutrition 0.000 claims description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 2
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- 239000010931 gold Substances 0.000 claims description 2
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 claims description 2
- 229910001416 lithium ion Inorganic materials 0.000 claims description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 claims description 2
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- 239000003208 petroleum Substances 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 2
- 239000010452 phosphate Substances 0.000 claims description 2
- 229910001414 potassium ion Inorganic materials 0.000 claims description 2
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- OGFYIDCVDSATDC-UHFFFAOYSA-N silver silver Chemical compound [Ag].[Ag] OGFYIDCVDSATDC-UHFFFAOYSA-N 0.000 claims description 2
- 229910001415 sodium ion Inorganic materials 0.000 claims description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 2
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 claims description 2
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 claims description 2
- 229940070710 valerate Drugs 0.000 claims description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 2
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- OJVAMHKKJGICOG-UHFFFAOYSA-N 2,5-hexanedione Chemical compound CC(=O)CCC(C)=O OJVAMHKKJGICOG-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- DCZNSJVFOQPSRV-UHFFFAOYSA-N n,n-diphenyl-4-[4-(n-phenylanilino)phenyl]aniline Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 DCZNSJVFOQPSRV-UHFFFAOYSA-N 0.000 description 4
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- UXKQNCDDHDBAPD-UHFFFAOYSA-N 4-n,4-n-diphenylbenzene-1,4-diamine Chemical compound C1=CC(N)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 UXKQNCDDHDBAPD-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
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- KBLZDCFTQSIIOH-UHFFFAOYSA-M tetrabutylazanium;perchlorate Chemical group [O-]Cl(=O)(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC KBLZDCFTQSIIOH-UHFFFAOYSA-M 0.000 description 3
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 3
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- PAPNRQCYSFBWDI-UHFFFAOYSA-N 2,5-Dimethyl-1H-pyrrole Chemical group CC1=CC=C(C)N1 PAPNRQCYSFBWDI-UHFFFAOYSA-N 0.000 description 1
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- C08G2261/312—Non-condensed aromatic systems, e.g. benzene
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- C08G2261/5222—Luminescence fluorescent electrofluorescent
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Abstract
一种聚(N,N‑二苯基‑4‑(2,5‑二甲基‑1H‑吡咯‑1‑基)苯胺)作为电致变色材料的应用，所述聚(N,N‑二苯基‑4‑(2,5‑二甲基‑1H‑吡咯‑1‑基)苯胺)如式(I)所示：
Description
技术领域
本发明属于电致变色材料技术领域，特别是涉及一种聚(N,N- 二苯基-4-(2,5-二甲基-1H-吡咯-1-基)苯胺)作为电致变色材料的应用及其制备方法。
背景技术
电致变色是材料的光学属性(反射率、透过率、吸收率等)在外加电场的作用下发生稳定、可逆的颜色变化的现象，在外观上表现为颜色和透明度的可逆变化。具有电致变色性能的材料称为电致变色材料，用电致变色材料做成的器件称为电致变色器件。电致变色材料在外电位或电流刺激下呈现可逆的颜色和吸收光谱变化。近几十年来，由于其在电子纸、智能窗、伪装材料等领域的广泛应用，引起了许多科学家的兴趣。自1969年Deb发表关于WO3基电致变色现象的专题报告以来，电致变色材料和器件的研究已经成为研究热点。电致变色材料分为无机电致变色材料和有机电致变色材料。与电致变色无机氧化物和金属配合物相比，有机聚合物尤其是导电聚合物作为电致变色材料，具有重量轻、易于加工、分子结构设计、变色丰富、响应时间短、成本低等优点。除了在可见光区域中普遍研究的电致变色外，近红外(NIR，750-3000nm)区域中的电致变色材料最近也得到了发展。
聚三苯胺及其衍生物是典型的电致变色材料之一，由于其氧化电位低、易质子酸掺杂、颜色对比度高，环境稳定性好等优点，具有很好的应用前景。然而，传统的三苯胺衍生物很难采用电化学阳极氧化法制备聚合物，这是因为三苯胺TPA易于氧化形成自由基阳离子，TPA+；而阳离子自由基不稳定，易发生尾对尾(对位)的偶合反应，从而失去两个质子生产四苯基联苯胺(TPB)；TPB相比于TPA更容易发生氧化，从而会失去1个电子变成TPB+；随后再失去一个电子变为 TPB2+，从而阻碍进一步的电化学聚合。研究表明，在三苯胺基团的对位上引入供电子基团，可以稳定电化学氧化形成的单阳离子自由基，从而电化学聚合形成长链聚合物。吡咯基团是含有一个氮杂原子的五元杂环化合物，是一种常见的具有氧化还原活性的供电子基团，其氧化电位为0.7V。同时，吡咯的的N原子和其α位上的活性较强，很容易失去电子形成对应的自由基离子。
发明内容
本发明的目的在于提供一种聚(N,N-二苯基-4-(2,5-二甲基-1H- 吡咯-1-基)苯胺)作为电致变色材料的应用及其制备方法，该聚合物薄膜具有可逆的颜色变化，光学对比度高，响应时间快。
为了解决上述技术问题，本发明提供了如下技术方案：
一种如式(I)所示的聚(N,N-二苯基-4-(2,5-二甲基-1H-吡咯-1- 基)苯胺)作为电致变色材料的应用。
式(I)中，n代表平均聚合度。
一种聚(N,N-二苯基-4-(2,5-二甲基-1H-吡咯-1-基)苯胺)的制备方法，所述式(I)所示的聚(N,N-二苯基-4-(2,5-二甲基-1H-吡咯-1- 基)苯胺)由如式(II)所示的N,N-二苯基-4-(2,5-二甲基-1H-吡咯-1- 基)苯胺单体通过电化学聚合制得；
其电化学聚合按照如下步骤进行：
将式(II)所示的N,N-二苯基-4-(2,5-二甲基-1H-吡咯-1-基)苯胺单体、支持电解质及电解溶剂组成电解液，加入到三电极电解池中，采用恒电位法、恒电流法或循环伏安法在工作电极上电沉积得到聚合物薄膜，所述的聚合物薄膜经过清洗、干燥即得所述的式(I)所示的聚(N,N-二苯基-4-(2,5-二甲基-1H-吡咯-1-基)苯胺)。
进一步，所述式(Ⅱ)所示的N,N-二苯基-4-(2,5-二甲基-1H-吡咯 -1-基)苯胺单体的初始浓度为10-4～10-1mol/L；优选初始终浓度为2 ×10-3mol/L。
进一步，所述的支持电解质为常用支持电解质，如一般由阴离子和阳离子按摩尔数1:1比例组成，所述阴离子为高氯酸根离子、四氟硼酸根离子、六氟磷酸根离子、六氟砷酸根离子、硝酸根离子、磺酸根离子、硫酸根离子、甲酸根离子、乙酸根离子、丙酸根离子、丁酸根离子、戊酸根离子或磷酸根离子；所述阳离子为钠离子、钾离子、锂离子、氢离子、铵根离子、四甲基铵离子、四乙基铵离子、四丁基铵离子、四正丙基铵离子或四正己基铵离子。优选所述的支持电解质为四丁基高氯酸铵、四丁基六氟磷酸铵。
进一步，所述的电解溶剂为常用溶剂，如N,N-二甲基甲酰胺、N,N- 二甲基乙酰胺、乙腈、甲苯、乙醇、甲醇、三氯甲烷、二氯甲烷、四氢呋喃、环己烷、吡啶、碳酸丙烯酯、苯乙腈、乙醚、乙酸、甲酸、盐酸、磷酸或石油醚，优选电解溶剂为二氯甲烷。
进一步，所述支持电解质的加入量以所述电解溶剂的体积计为 10-3～10-1mol/L；优选所述支持电解质的加入量以所述电解溶剂的体积计为10-1mol/L。
进一步，所述的三电极电解池中，工作电极可以是金、铂、铜、钛、不锈钢、ITO电极，优选为ITO电极；参比电极是银-银离子电极、银 -氯化银电极、饱和甘汞电极，优选为银-氯化银电极；对电极为铂、钛、不锈钢，优选为铂。
进一步，优选采用恒电位法进行电化学聚合，电压范围为1.2～1.4V，聚合电量为0.05C～0.5C。
本发明所述式(Ⅱ)所示的N,N-二苯基-4-(2,5-二甲基-1H-吡咯-1- 基)苯胺单体的制备方法可按如下步骤进行：
式(Ⅲ)所示的4-二苯氨基苯胺和式(Ⅳ)所示的2,5-己二酮在酸性物质的作用下，在有机溶剂中，在110～150℃进行反应，反应完全后所得反应液，经分离纯化得到式(Ⅱ)所示的N,N-二苯基-4-(2,5- 二甲基-1H-吡咯-1-基)苯胺单体。
进一步，所述的酸性物质为冰醋酸。
进一步，所述的有机溶剂为甲苯。
进一步，所述式(Ⅲ)所示的4-二苯氨基苯胺、式(Ⅳ)所示的 2,5-己二酮、酸性物质的投料物质的量之比为1:1～1.5:1～10。
进一步，所述的反应时间为10～24h。
进一步，所述反应液的分离纯化步骤为：反应结束后，将得到的反应液过滤，除去滤液，用无水乙醇淋洗过滤固体产物，所得固体产物烘干后，制得式(Ⅱ)所示的N,N-二苯基-4-(2,5-二甲基-1H-吡咯-1- 基)苯胺单体。
本发明提供的式(I)所示的聚(N,N-二苯基-4-(2,5-二甲基-1H- 吡咯-1-基)苯胺)在不同电压下具有可逆的颜色变化(即随着施加电压的升高，由浅色变为橙红色再进一步变为蓝色；当电压逐渐降低后，颜色又变回原来的浅色)、光学对比度较高、响应时间快的特点。
在三苯胺对位上引入具有电化学氧化还原活性的2,5-二甲基吡咯基团，合成了N,N-二苯基-4-(2,5-二甲基-1H-吡咯-1-基)苯胺，通过电化学聚合法制备了相应的聚合物薄膜，并进一步考察这些聚合物薄膜在电致变色领域的应用。
与现有技术相比，本发明的优势在于：
(1)采用电化学聚合法，制备了一种新型的聚三苯胺类衍生物—聚(N,N-二苯基-4-(2,5-二甲基-1H-吡咯-1-基)苯胺)；
(2)本发明制备的电致变色材料与现有的其他电致变色材料相比，具有多色显示、快速响应和高颜色对比度等优点。
附图说明
图1为N,N-二苯基-4-(2,5-二甲基-1H-吡咯-1-基)苯胺的循环伏安聚合曲线。
图2为聚(N,N-二苯基-4-(2,5-二甲基-1H-吡咯-1-基)苯胺)薄膜的扫描电镜照片。其中(a)10000x倍率下；(b)30000x倍率下；(c) 截面图。
图3为聚(N,N-二苯基-4-(2,5-二甲基-1H-吡咯-1-基)苯胺)薄膜不同电压下的光谱电化学曲线及颜色变化。
图4为聚(N,N-二苯基-4-(2,5-二甲基-1H-吡咯-1-基)苯胺)薄膜在不同波长下的响应时间和对比度曲线图。
具体实施方式
以下通过实施例对本发明的技术方案作进一步说明，但本发明的保护范围不限于此。
实施例1：
一种(N,N-二苯基-4-(2,5-二甲基-1H-吡咯-1-基)苯胺单体的合成方法，过程如下：
在预先经过干燥处理的100mL两口烧瓶中加入4-氨基三苯胺 (0.52g，2mmol)，2-5-己二酮(0.34g，3mmol)，随后分别加入甲苯 (15ml)、冰醋酸(30ml)。搅拌，待其溶解后，升温至130℃，回流反应48h，达到反应终点。反应后残余液体通过过滤除去，得到固体粗产品。粗产品经乙醇清洗后烘干得最终产物0.3206g，产率47％，产物为浅黄色固体粉末。
1H NMR(500MHz,DMSO)δ7.77(dd,J＝2.8,1.2Hz,1H),7.66–7.61 (m,3H),7.51(dd,J＝5.0,1.2Hz,1H),7.32(t,J＝7.9Hz,4H),7.08–6.97 (m,6H),5.77(s,1H),2.01(s,6H).MS(EI):m/z＝338.2(M+).
实施例2：
一种(N,N-二苯基-4-(2,5-二甲基-1H-吡咯-1-基)苯胺单体的电化学聚合方法，过程如下：
预先经过干燥处理的100mL烧杯作为三电极电解池，加入50mL 含有2×10-3mol·L-1(N,N-二苯基-4-(2,5-二甲基-1H-吡咯-1-基)苯胺单体和10-1mol/L四丁基高氯酸铵/二氯甲烷溶液作为电解溶液，ITO 玻璃作为工作电极，铂丝作为对电极，银-氯化银电极作为参比电极，采用恒电位聚合法进行聚合，聚合电压1.4V，聚合电量为0.3C。待聚合完成后，将附有聚合物薄膜的ITO电极在无水乙醇中清洗30s，用N2吹干后得到干燥的聚(N,N-二苯基-4-(2,5-二甲基-1H-吡咯-1-基) 苯胺薄膜。
此外，通过对(N,N-二苯基-4-(2,5-二甲基-1H-吡咯-1-基)苯胺单体进行多次循环伏安曲线测试(图1)，发现随着扫描圈数的增加，氧化峰和还原峰电流不断增强，峰面积不断增大，也表明在ITO表面形成了聚(N,N-二苯基-4-(2,5-二甲基-1H-吡咯-1-基)苯胺薄膜。
我们用扫描电镜观察了聚合物的微观形貌，如图2所示，可以看出聚合物薄膜在ITO上是一些比较松散的球状颗粒，这些球状颗粒的直径大概在230nm左右，而膜厚大致在470nm。
实施例3：聚(N,N-二苯基-4-(2,5-二甲基-1H-吡咯-1-基)苯胺)的电致变色性质
将实施例2中制备的附在ITO玻璃上的聚(N,N-二苯基-4-(2,5- 二甲基-1H-吡咯-1-基)苯胺)薄膜放入三电极电解池中，以10-1mol/L 四丁基高氯酸铵/二氯甲烷溶液作为电解溶液，其中工作电极为附有聚 (N,N-二苯基-4-(2,5-二甲基-1H-吡咯-1-基)苯胺)薄膜的ITO玻璃，对电极为铂丝，参比电极为银-氯化银电极。采用电化学工作站与紫外- 可见光谱仪联用技术，电化学工作站设置为恒电位，紫外-可见光谱仪设置为吸收，扫描范围为1100～300nm。最终得到的数据如图4所示，图4可以看出，0V时，在330nm处有明显的吸收峰，归属于TPA 聚合物主链的π-π*跃迁。随着电压的增加，在477nm处出现新的吸收峰，归属于三苯胺与烷基吡咯之间的电荷转移；继续增大电压，会逐渐生成极化子和双极化子，从而在720nm处有明显的吸收峰的出现，同时330nm处的吸收峰强度随着电压的升高而不断下降。同时，可以观察到聚(N,N-二苯基-4-(2,5-二甲基-1H-吡咯-1-基)苯胺)薄膜由中性态到氧化态逐渐从浅色变为橙红色再向蓝色转变的颜色变化，这一变色现象说明聚(N,N-二苯基-4-(2,5-二甲基-1H-吡咯-1-基)苯胺)具有多色显示的特性，有望应用于电致变色领域。
为了检测聚(N,N-二苯基-4-(2,5-二甲基-1H-吡咯-1-基)苯胺)薄膜的响应速度和对比度，我们采用电化学工作站与紫外-可见光谱仪联用技术，电化学工作站设置为多电位阶跃：低电位为0V，高电位为 1.4V，电位脉冲宽度为5s，扫描时间为200s；紫外-可见光谱仪设置为光谱动力学，波长分别设置为720nm和1100nm。最终得到的数据如图4，可以看出在720nm处，对比度为35.90％，对应的响应时间分别为1.55s(着色时间)、1.15s(褪色时间)；在1100nm处，对比度为13.42％，响应时间为0.72s(着色时间)、0.98s(褪色时间)。因此，聚(N,N-二苯基-4-(2,5-二甲基-1H-吡咯-1-基)苯胺)薄膜具有较高的光学对比度和快速的响应时间。
Claims (9)
1.一种如式(I)所示的聚(N,N-二苯基-4-(2,5-二甲基-1H-吡咯-1-基)苯胺)作为电致变色材料的应用；
式(I)中，n代表平均聚合度。
2.一种如权利要求1所述的聚(N,N-二苯基-4-(2,5-二甲基-1H-吡咯-1-基)苯胺)的制备方法，其特征在于：通过电化学聚合法制得聚(N,N-二苯基-4-(2,5-二甲基-1H-吡咯-1-基)苯胺)，过程如下：将电解溶剂、式(II)所示的N,N-二苯基-4-(2,5-二甲基-1H-吡咯-1-基)苯胺单体、支持电解质及电解溶剂组成电解液，加入到三电极电解池中，采用恒电位法、恒电流法或循环伏安法在工作电极上电沉积得到聚合物薄膜，所述的薄膜经过清洗、干燥即得所述的式(I)所示的聚(N,N-二苯基-4-(2,5-二甲基-1H-吡咯-1-基)苯胺)；
3.如权利要求2所述的聚(N,N-二苯基-4-(2,5-二甲基-1H-吡咯-1-基)苯胺)的制备方法，其特征在于，所述式(Ⅱ)所示的N,N-二苯基-4-(2,5-二甲基-1H-吡咯-1-基)苯胺单体的初始浓度为2×10-3mol/L。
4.如权利要求2所述的聚(N,N-二苯基-4-(2,5-二甲基-1H-吡咯-1-基)苯胺)的制备方法，其特征在于，所述的支持电解质为由阴离子和阳离子按物质的量之比1:1比例组成，所述阴离子为高氯酸根离子、四氟硼酸根离子、六氟磷酸根离子、六氟砷酸根离子、硝酸根离子、磺酸根离子、硫酸根离子、甲酸根离子、乙酸根离子、丙酸根离子、丁酸根离子、戊酸根离子或磷酸根离子；所述阳离子为钠离子、钾离子、锂离子、氢离子、铵根离子、四甲基铵离子、四乙基铵离子、四丁基铵离子、四正丙基铵离子或四正己基铵离子。
5.权利要求2所述的聚(N,N-二苯基-4-(2,5-二甲基-1H-吡咯-1-基)苯胺)的制备方法，其特征在于，所述的电解溶剂为N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、乙腈、甲苯、乙醇、甲醇、三氯甲烷、二氯甲烷、四氢呋喃、环己烷、吡啶、碳酸丙烯酯、苯乙腈、乙醚、乙酸、甲酸、盐酸、磷酸或石油醚。
6.权利要求2所述的聚(N,N-二苯基-4-(2,5-二甲基-1H-吡咯-1-基)苯胺)的制备方法，其特征在于，所述支持电解质的加入量以所述电解溶剂的体积计为10-3～10-1mol/L。
7.权利要求2所述的聚(N,N-二苯基-4-(2,5-二甲基-1H-吡咯-1-基)苯胺)的制备方法，其特征在于，所述的三电极电解池中，所述的工作电极为金、铂、铜、钛、不锈钢或ITO电极；参比电极是银-银离子电极、银-氯化银电极或饱和甘汞电极；对电极为铂、钛或不锈钢。
8.如权利要求7所述的聚(N,N-二苯基-4-(2,5-二甲基-1H-吡咯-1-基)苯胺)的制备方法，其特征在于：所述的参比电极是银-氯化银电极。
9.权利要求2所述的聚(N,N-二苯基-4-(2,5-二甲基-1H-吡咯-1-基)苯胺)的制备方法，其特征在于：采用恒电位法进行电化学聚合，电压范围为1.2～1.4V，聚合电量为0.05C～0.5C。
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| "Multielectrochromic property of N-phenylnaphthalen-2-amine and N-(4-(1H-pyrrol-1-yl)phenyl)-N-phenylnaphthalen-2-amine";Cheng Zhang，et al;《Journal of Electroanalytical Chemistry》;20110606;第660卷;第45-49页 * |
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