CN106187817A - 具有聚集诱导发光性质和压致变色性质的荧光材料 - Google Patents
具有聚集诱导发光性质和压致变色性质的荧光材料 Download PDFInfo
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- 239000000463 material Substances 0.000 title claims abstract description 35
- 238000004220 aggregation Methods 0.000 title claims abstract description 14
- 230000002776 aggregation Effects 0.000 title claims abstract description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- -1 4-hydroxymethyl phenyl Chemical group 0.000 claims description 12
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 2
- KLIDCXVFHGNTTM-UHFFFAOYSA-N 2,6-dimethoxyphenol Chemical group COC1=CC=CC(OC)=C1O KLIDCXVFHGNTTM-UHFFFAOYSA-N 0.000 claims description 2
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 2
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 150000003549 thiazolines Chemical class 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 22
- 238000000227 grinding Methods 0.000 abstract description 4
- 239000002086 nanomaterial Substances 0.000 abstract description 2
- 239000003960 organic solvent Substances 0.000 abstract description 2
- POXIZPBFFUKMEQ-UHFFFAOYSA-N 2-cyanoethenylideneazanide Chemical group [N-]=C=[C+]C#N POXIZPBFFUKMEQ-UHFFFAOYSA-N 0.000 abstract 1
- 238000006482 condensation reaction Methods 0.000 abstract 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 38
- 150000001875 compounds Chemical class 0.000 description 30
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 28
- 238000002360 preparation method Methods 0.000 description 26
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 239000011734 sodium Substances 0.000 description 14
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 10
- 238000005160 1H NMR spectroscopy Methods 0.000 description 10
- 239000002131 composite material Substances 0.000 description 10
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- 238000012512 characterization method Methods 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 208000035126 Facies Diseases 0.000 description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 238000002189 fluorescence spectrum Methods 0.000 description 5
- 150000002825 nitriles Chemical class 0.000 description 5
- 239000012264 purified product Substances 0.000 description 5
- XJKSTNDFUHDPQJ-UHFFFAOYSA-N 1,4-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=C(C=2C=CC=CC=2)C=C1 XJKSTNDFUHDPQJ-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000004327 boric acid Substances 0.000 description 4
- 229960000935 dehydrated alcohol Drugs 0.000 description 4
- 229910052763 palladium Inorganic materials 0.000 description 4
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 3
- DPULZASAHQHNIY-UHFFFAOYSA-N 2,5-bis(4-hydroxyphenyl)terephthalaldehyde Chemical compound Oc1ccc(cc1)-c1cc(C=O)c(cc1C=O)-c1ccc(O)cc1 DPULZASAHQHNIY-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical class OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 3
- 230000001427 coherent effect Effects 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- VSUKSWCSOBXUFG-UHFFFAOYSA-N 2,5-dibromoterephthalaldehyde Chemical compound BrC1=CC(C=O)=C(Br)C=C1C=O VSUKSWCSOBXUFG-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 150000002460 imidazoles Chemical class 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000000171 quenching effect Effects 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- VOAAEKKFGLPLLU-UHFFFAOYSA-N (4-methoxyphenyl)boronic acid Chemical compound COC1=CC=C(B(O)O)C=C1 VOAAEKKFGLPLLU-UHFFFAOYSA-N 0.000 description 1
- NRIYPIBRPGAWDD-UHFFFAOYSA-N (5-methylthiophen-2-yl)boronic acid Chemical compound CC1=CC=C(B(O)O)S1 NRIYPIBRPGAWDD-UHFFFAOYSA-N 0.000 description 1
- XQQBUAPQHNYYRS-UHFFFAOYSA-N 2-methylthiophene Chemical compound CC1=CC=CS1 XQQBUAPQHNYYRS-UHFFFAOYSA-N 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- 206010011224 Cough Diseases 0.000 description 1
- DDBSDHONALUWPM-UHFFFAOYSA-N N#CC(C#N)=Cc1cc(-c2ccccc2)c(C=C(C#N)C#N)cc1-c1ccccc1 Chemical compound N#CC(C#N)=Cc1cc(-c2ccccc2)c(C=C(C#N)C#N)cc1-c1ccccc1 DDBSDHONALUWPM-UHFFFAOYSA-N 0.000 description 1
- LHJCYYZDVRHRBR-UHFFFAOYSA-N [4-(hydroxymethyl)phenoxy]boronic acid Chemical compound OCC1=CC=C(OB(O)O)C=C1 LHJCYYZDVRHRBR-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 1
- MXOSTENCGSDMRE-UHFFFAOYSA-N butyl-chloro-dimethylsilane Chemical compound CCCC[Si](C)(C)Cl MXOSTENCGSDMRE-UHFFFAOYSA-N 0.000 description 1
- ZTAYJSRSQODHEO-UHFFFAOYSA-N butylsilicon Chemical group CCCC[Si] ZTAYJSRSQODHEO-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- CYEFKCRAAGLNHW-UHFFFAOYSA-N furan-3-ylboronic acid Chemical compound OB(O)C=1C=COC=1 CYEFKCRAAGLNHW-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000003471 mutagenic agent Substances 0.000 description 1
- 231100000707 mutagenic chemical Toxicity 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- OHOVBSAWJQSRDD-UHFFFAOYSA-N thiophen-2-yloxyboronic acid Chemical compound OB(O)OC1=CC=CS1 OHOVBSAWJQSRDD-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 230000003313 weakening effect Effects 0.000 description 1
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
- C07C255/34—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring with cyano groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by unsaturated carbon chains
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- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
- C07C255/36—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by hydroxy groups
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- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
- C07C255/37—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by etherified hydroxy groups
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- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
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Abstract
本发明公开了一类具有聚集诱导发光和压致变色性质的荧光材料,该荧光材料结构式为
Description
技术领域
本发明属于荧光材料技术领域,具体涉及一类具有聚集诱导发光性质和压致变色性质的荧光材料。
背景技术
荧光材料由于在光电器件、环境传感器、生物科学等领域具有重大的应用价值,近年来引起了科学家们的极大关注。传统荧光化合物在溶液中显示很强的荧光,但是大多数在聚集状态时呈现荧光减弱甚至淬灭的现象,即聚集诱导荧光淬灭效应(aggregation-caused quenching,ACQ)。鉴于荧光材料常常被用于聚集或固体薄膜,因此,ACQ现象限制了荧光材料在特定情况下的应用前景。2001年,香港科技大学唐本忠院士课题组发现了一类具有螺旋桨结构的分子具有奇特的发光行为:当该类分子溶解在溶液中时,荧光很弱或是不发光,但在固态或聚集状态时,则产生强烈的荧光。他们把这一现象命名为聚集诱导发光(aggregation-induced emission,AIE)现象。AIE现象与传统的ACQ现象恰好相反,利用这一新特性可以进一步拓宽有机荧光化合物在固体或聚集状态领域的应用。近年来,科学家们努力开发新的AIE体系及其在有机发光二极管、生物探针、化学传感器和细胞成像等领域的应用。由于大多数的具有AIE性质的化合物具有扭曲的分子构象,导致其分子堆积相对松散,在受到外界刺激时由于堆积方式的改变会呈现不同的发光行为,即压致变色性。压致变色是指当受到外力刺激,如加热、溶剂熏蒸或研磨时,材料的荧光(如发光强度、发射波长)随之发生改变的性质。具有压致变色性质的荧光材料是一种新型的智能材料,它在应力传感器、信息存储、荧光开关和发光器件等领域具有非常广泛的应用。但是到目前为止已经报道的具有压致变色性质的发光材料还不是很多,所以设计合成新型的具有压致变色性质的聚集诱导发光材料仍然被迫切需要。
发明内容
本发明所要解决的技术问题在于提供一类具有聚集诱导发光及压致变色效应的新型荧光材料。
解决上述技术问题所采用的技术方案是:该荧光材料的结构式如下所示:
式中Ar代表苯基、C1~C4烷基取代苯基、C1~C4烷氧基取代苯基、4-羟甲基苯基、噻吩基、C1~C4烷基取代噻吩基、呋喃基、羟基取代苯基、卤代苯基、萘基、N-碳酸叔丁酯-2-吡咯基、4-叔丁基二甲基硅氧基苯基中的任意一种,具体如苯基、4-甲基苯基、2-甲基苯基、4-甲氧基苯基、2-甲氧基苯基、2,6-二甲氧基苯基、4-羟甲基苯基、2-噻吩基、5-甲基-2-噻吩基、3-呋喃基、4-羟基苯基、4-氯苯基、4-氟苯基、1-萘基、2-萘基、N-碳酸叔丁酯-2-吡咯基、4-叔丁基二甲基硅氧基苯基等。
上述具有聚集诱导发光性质和压致变色性质的荧光材料(除Ar代表4-叔丁基二甲基硅氧基苯基)的制备方如下:
1、以DMF为溶剂,将2,5-二溴苯-1,4-二甲醛、式I所示的芳基硼酸、醋酸钯按摩尔比为1:2.5:0.05,在碱性条件下室温反应至完全,分离纯化产物,得到式II所示的2,5-二芳基-1,4-二甲醛。
2、以无水乙醇为溶剂,将式II所示的2,5-二芳基-1,4-二甲醛与丙二腈按摩尔比为1:2.05,在碱性条件下室温反应至完全,分离纯化产物,得到荧光材料。
当Ar代表4-叔丁基二甲基硅氧基苯基时,该荧光材料的制备方法为:
1、以DMF为溶剂,将2,5-二溴苯-1,4-二甲醛、4-羟基苯硼酸、醋酸钯按摩尔比为1:2.5:0.05,在碱性条件下室温反应至完全,分离纯化产物,得到4,4”-二羟基-[1,1':4',1”-三联苯]-2',5'-二甲醛。
2、以DMF为溶剂,将4,4”-二羟基-[1,1':4',1”-三联苯]-2',5'-二甲醛与咪唑、叔丁基二甲基氯硅烷(TBDMS-Cl)按摩尔比为1:4:3,室温反应至完全,分离纯化产物,得到式III所示的44”-二甲基叔丁基硅基-[1,1':4',1”-三联苯]-2'5'-二甲醛。
3、以无水乙醇为溶剂,将4,4”-二甲基叔丁基硅基-[1,1':4',1”-三联苯]-2',5'-二甲醛与丙二腈按摩尔比为1:2.05,在碱性条件下室温反应至完全,分离纯化产物,得到荧光材料——1,4-二(4-(2,5-二甲基叔丁基)硅氧基)-2,2'-(1,4-亚苯基二(亚甲基))丙二腈。
本发明荧光材料在普通有机溶剂中具有良好的溶解性,而在水中几乎不溶解,可形成纳米聚集体,具有聚集诱导发光特性。同时通过研磨,该类荧光材料的荧光发射波长会向长波方向移动,用二氯甲烷熏蒸后荧光发射波长则会恢复,具有压致变色的性质。
附图说明
图1是实施例1制备的化合物在丙酮与水的混合体系中的荧光发射光谱图。
图2是实施例1制备的化合物在丙酮与水的混合体系中的发射的相对强度图。
图3是实施例2制备的化合物在丙酮与水的混合体系中的荧光发射光谱图。
图4是实施例2制备的化合物在丙酮与水的混合体系中的发射的相对强度图。
图5是实施例3制备的化合物在丙酮与水的混合体系中的荧光发射光谱图。
图6是实施例3制备的化合物在丙酮与水的混合体系中的发射的相对强度图。
图7是实施例4制备的化合物在丙酮与水的混合体系中的荧光发射光谱图。
图8是实施例4制备的化合物在丙酮与水的混合体系中的发射的相对强度图。
图9是实施例6制备的化合物在丙酮与水的混合体系中的荧光发射光谱图。
图10是实施例6制备的化合物在丙酮与水的混合体系中的发射的相对强度图。
图11是实施例7制备的化合物在丙酮与水的混合体系中的荧光发射光谱图。
图12是实施例7制备的化合物在丙酮与水的混合体系中的发射的相对强度图。
图13是实施例8制备的化合物在丙酮与水的混合体系中的荧光发射光谱图。
图14是实施例8制备的化合物在丙酮与水的混合体系中的发射的相对强度图。
图15是实施例9制备的化合物在丙酮与水的混合体系中的荧光发射光谱图。
图16是实施例9制备的化合物在丙酮与水的混合体系中的发射的相对强度图。
图17是实施例10制备的化合物在丙酮与水的混合体系中的荧光发射光谱图。
图18是实施例10制备的化合物在丙酮与水的混合体系中的发射的相对强度图。
图19是实施例2制备的化合物研磨和二氯甲烷熏蒸前后的荧光光谱图。
图20是实施例3制备的化合物研磨和二氯甲烷熏蒸前后的荧光光谱图。
图21是实施例4制备的化合物研磨和二氯甲烷熏蒸前后的荧光光谱图。
图22是实施例5制备的化合物研磨和二氯甲烷熏蒸前后的荧光光谱图。
图23是实施例10制备的化合物研磨和二氯甲烷熏蒸前后的荧光光谱图。
具体实施方式
下面结合附图和实施例对本发明进一步详细说明,但本发明的保护范围不仅限于这些实施例。
实施例1
合成结构式如下的1,4-二苯基-2,2'-(1,4-亚苯基二(亚甲基))丙二腈
1、将0.0584g(0.2mmol)2,5-二溴苯-1,4-二甲醛、0.27mL DMF、0.13mL 2mol/LNa2CO3水溶液、0.0609g(0.5mmol)苯硼酸加入到5mL圆底烧瓶中,搅拌10分钟后,向反应液中加入0.0424g(0.01mmol)醋酸钯,待反应完成后,用乙酸乙酯萃取(3×5mL),合并有机相,有机相经无水硫酸钠干燥、过滤、旋干、石油醚与乙酸乙酯的体积比为20:1的混合液柱层析,得到1,1':4',1”-三联苯-2',5'-二甲醛。
2、向25mL圆底烧瓶中加入0.0400g(1.05mmol)1,1':4',1”-三联苯-2',5'-二甲醛,并加入无水乙醇使其溶解,然后加入0.1419g(2.15mmol)丙二腈和0.05mL 1mol/L的NaOH水溶液,在室温下搅拌2.5小时,析出固体,过滤,得到1,4-二苯基-2,2'-(1,4-亚苯基二(亚甲基))丙二腈,其产率为71%,结构表征数据为:1H-NMR(400MHz,d6-DMSO)δ(ppm):8.35(s,1H),8.21(s,1H),7.62-7.56(m,3H,Ar H),7.50(d,2H,J=7.3Hz,ArH);13C-NMR(101MHz,d6-DMSO)δ(ppm):160.26,141.51,136.97,132.99,130.77,129.93,129.05,113.58,112.91,87.55,79.19.HRMS(ESI-TOF)m/z:[M+Na]+理论值C26H14N4Na,405.1116,实测值405.1117。
实施例2
合成结构式如下的1,4-二(3-呋喃基)-2,2'-(1,4-亚苯基二(亚甲基))丙二腈
将实施例1中的苯硼酸用等物质的量的3-呋喃硼酸替换,其他步骤与实施例1相同,得到1,4-二(3-呋喃基)-2,2'-(1,4-亚苯基二(亚甲基))丙二腈,其产率为63%,结构表征数据为:1H-NMR(300MHz,CDCl3)δ(ppm):8.24(s,1H),8.05(s,1H),7.64(t,1H,J=1.6Hz),7.55(s,1H),6.62-6.61(q,1H);13C-NMR(101MHz,CDCl3)δ(ppm):157.36,145.09,142.34,134.28,132.85,130.21,122.40,112.82,111.99,111.35,87.65.HRMS(ESI-TOF)m/z:[M+Na]+理论值C22H10N4O2Na,385.0701,实测值385.0703。
实施例3
合成结构式如下的1,4-二(4-甲氧基苯基)-2,2'-(1,4-亚苯基二(亚甲基))丙二腈
将实施例1中的苯硼酸用等物质的量的4-甲氧基苯硼酸替换,其他步骤与实施例1相同,得到1,4-二(4-甲氧基苯基)-2,2'-(1,4-亚苯基二(亚甲基))丙二腈,其产率为69%,结构表征数据为:1H-NMR(400MHz,CDCl3)δ(ppm):8.22(s,1H),7.84(s,1H),7.27(d,2H,J=8.5Hz,Ar H),7.07(d,2H,J=8.5Hz,Ar H),3.91(s,3H,CH3);13C-NMR(101MHz,CDCl3)δ(ppm):160.97,158.77,142.91,132.79,131.50,130.76,128.94,115.03,113.09,112.29,86.53,55.69.HRMS(ESI-TOF)m/z:[M+Na]+理论值C28H18N4O2Na,465.1327,实测值465.1330。
实施例4
合成结构式如下的1,4-二(4-羟甲基苯基)-2,2'-(1,4-亚苯基二(亚甲基))丙二腈
将实施例1中的苯硼酸用等物质的量的4-羟甲基苯硼酸替换,其他步骤与实施例1相同,得到1,4-二(4-羟甲基苯基)-2,2'-(1,4-亚苯基二(亚甲基))丙二腈,其产率为40%,结构表征数据为:1H-NMR(400MHz,CDCl3)δ(ppm):8.32(s,1H),8.19(s,1H),7.53(d,2H,J=8.0Hz,Ar H),7.45(d,2H,J=8.0Hz,Ar H),5.34(t,1H,J=5.7Hz),4.61(d,2H,J=5.6Hz,CH2);13C-NMR(100MHz,CDCl3)δ(ppm):160.24,143.04,141.41,135.26,132.90,130.61,129.92,113.58,112.86,87.28,62.48。
实施例5
合成结构式如下的1,4-二(2-噻吩基)-2,2'-(1,4-亚苯基二(亚甲基))丙二腈
将实施例1中的苯硼酸用等物质的量的2-噻吩硼酸替换,其他步骤与实施例1相同,得到1,4-二(2-噻吩基)-2,2'-(1,4-亚苯基二(亚甲基))丙二腈,其产率为64%,结构表征数据为:1H-NMR(300MHz,d6-DMSO)δ(ppm):8.60(s,1H),8.25(s,1H),7.90(d,1H,J=4.5Hz),7.38-7.31(m,2H);13C-NMR(100MHz,d6-DMSO)δ(ppm):160.06,138.76,134.41,133.12,131.45,131.11,130.65,129.53,114.12,113.24,88.87。
实施例6
合成结构式如下的1,4-二(4-羟基苯基)-2,2'-(1,4-亚苯基二(亚甲基))丙二腈
将实施例1中的苯硼酸用等物质的量的4-羟基苯硼酸替换,其他步骤与实施例1相同,得到1,4-二(4-羟基苯基)-2,2'-(1,4-亚苯基二(亚甲基))丙二腈,其产率为45%,结构表征数据为:1H-NMR(400MHz,d6-DMSO)δ(ppm):9.95(s,1H),8.30(s,1H),8.10(s,1H),7.28(d,2H,J=8.5Hz,Ar H),6.96(d,2H,J=8.5Hz,Ar H);13C-NMR(101MHz,d6-DMSO)δ(ppm):160.61,158.44,140.90,132.61,131.35,130.24,127.63,115.84,113.71,113.02,86.61.HRMS(ESI-TOF)m/z:[M+Na]+理论值C26H14N4O2Na,437.1014,实测值437.1017。
实施例7
合成结构式如下的1,4-二(5-甲基-2-噻吩基)-2,2'-(1,4-亚苯基二(亚甲基))丙二腈
将实施例1中的苯硼酸用等物质的量的5-甲基-2-噻吩硼酸(0.0710g)替换,其他步骤与实施例1相同,得到1,4-二(5-甲基-2-噻吩基)-2,2'-(1,4-亚苯基二(亚甲基))丙二腈,其产率为75%,结构表征数据为:1H-NMR(400MHz,CDCl3)δ(ppm):8.21(s,1H),8.07(s,1H),6.89(s,2H),2.58(s,3H,CH3);13C-NMR(75MHz,CDCl3)δ(ppm):157.93,145.48,135.83,1 50,132.32,130.89,130.77,127.40,113.02,111.95,87.32,15.67.HRMS(ESI-TOF)m/z:[M+Na]+理论值C24H14N4S2Na,445.0558,实测值445.0563。
实施例8
合成结构式如下的1,4-二(2,5-二甲氧基苯基)-2,2'-(1,4-亚苯基二(亚甲基))丙二腈
将实施例1中的苯硼酸用等物质的量的2,6-二甲氧基苯硼酸替换,其他步骤与实施例1相同,得到1,4-二(2,5-二甲氧基苯基)-2,2'-(1,4-亚苯基二(亚甲基))丙二腈,其产率为87%,结构表征数据为:1H-NMR(400MHz,CDCl3)δ(ppm):8.14(s,1H,),7.63(s,1H,),7.45-7.41(t,2H,J=8.4Hz,ArH),6.70(d,2H,J=8.4Hz,ArH),3.79(s,6H,CH3);13C-NMR(101MHz,CDCl3)δ(ppm):160.18,157.73,136.20,134.61,132.01,131.66,113.78,113.37,112.03,104.24,84.80,55.98。
实施例9
合成结构式如下的1,4-二(N-碳酸叔丁酯-2-吡咯基)-2,2'-(1,4-亚苯基二(亚甲基))丙二腈
将实施例1中的苯硼酸用等物质的量的N-碳酸叔丁酯-2-吡咯硼酸(0.1055g)替换,其他步骤与实施例1相同,得到1,4-二(N-碳酸叔丁酯-2-吡咯基)-2,2'-(1,4-亚苯基二(亚甲基))丙二腈,其产率为59%,结构表征数据为:1H-NMR(400MHz,CDCl3)δ(ppm):8.17(s,1H),7.68(s,1H),7.46-7.45(t,2H,J1=2.6Hz,J2=2.2Hz,CH),6.35(d,2H,J=3.1Hz,CH),1.47(s,9H,CH3);13C-NMR(101MHz,CDCl3)δ(ppm):158.87,157.44,142.93,132.73,131.51,130.77,139.48,121.01,113.07,112.31,86.48,25.77,18.37,-4.16.HRMS(ESI-TOF)m/z:[M+Na]+理论值C32H28N6O4Na,538.2070,实测值538.2074。
实施例10
合成结构式如下的1,4-二(4-(2,5-二甲基叔丁基)硅氧基)-2,2'-(1,4-亚苯基二(亚甲基))丙二腈
将0.0584g(0.2mmol)2,5-二溴苯-1,4-二甲醛、0.27mL DMF、0.13mL2mol/L Na2CO3水溶液、0.0690g(0.5mmol)4-羟基苯硼酸加入到5mL圆底烧瓶中,搅拌10分钟后,向反应液中加入0.0424g(0.01mmol)醋酸钯,待反应完成后,用乙酸乙酯萃取(3×5mL),合并有机相,有机相经无水硫酸钠干燥、过滤、旋干、石油醚与乙酸乙酯的体积比为10:1的混合液柱层析,得到4,4”-二羟基-[1,1':4',1”-三联苯]-2',5'-二甲醛。
2、向25mL圆底烧瓶中加入0.03g(0.094mmol)4,4”-二羟基-[1,1':4',1”-三联苯]-2',5'-二甲醛和5mL DMF,室温下搅拌使其完全溶解,再加入0.026g(0.376mmol)咪唑和0.043g(0.282mmol)叔丁基二甲基氯硅烷(TBDMS-Cl),室温下搅拌过夜,反应完成后,加入10mL蒸馏水,然后用乙酸乙酯(3×8mL)萃取,合并有机相,有机相经无水硫酸钠干燥、过滤,旋干、石油醚与乙酸乙酯的体积比为20:1的混合液柱层析,得到4,4”-二甲基叔丁基硅基-[1,1':4',1”-三联苯]-2',5'-二甲醛。
3、向25mL圆底烧瓶中加入0.5480g(1mmol)4,4”-二甲基叔丁基硅基-[1,1':4',1”-三联苯]-2',5'-二甲醛,并加入无水乙醇使其溶解,然后加入0.1353g(2.05mmol)丙二腈和0.05mL 1mol/L的NaOH水溶液,在室温下搅拌2.5小时,过滤,得到1,4-二(4-(2,5-二甲基叔丁基)硅氧基)-2,2'-(1,4-亚苯基二(亚甲基))丙二腈,其产率为82%,结构表征数据为:1H-NMR(400MHz,CDCl3)δ(ppm):8.21(s,1H),7.85(s,1H),7.20(d,2H,J=8.5Hz,ArH),7.01(d,2H,J=8.5Hz,ArH),1.02(s,9H,CH3),0.28(s,6H,CH3);13C-NMR(101MHz,CDCl3)δ(ppm):158.87,157.43,142.93,132.73,131.51,130.77,129.48,121.00,113.07,112.31,86.49,25.77,18.37,-4.16.HRMS(ESI-TOF)m/z:[M+Na]+理论值C38H42N4O2Si2Na,665.2744,实测值665.2745。
发明人将实施例1~4及6~10制备的化合物分别与丙酮和蒸馏水按不同体积比混合,采用日立F-7000荧光分光光度计测试混合体系的AIE性质,结果见图1~18。由图可见,此类化合物均具有聚集诱导发光性质。
发明人采用日立F-7000荧光分光光度计测试实施例2、3、4、5、10制备的化合物的压致变色性质,结果见图19~23。由图可见,实施例2、3、4、5、10制备的化合物的粉末荧光发射峰分别位于543nm、510nm、526nm、562nm、513nm处。当分别将其研磨后,光谱发生红移,最大发射峰位分别在543nm、544nm、562nm、574nm、527nm,半峰宽也出现增大趋势。研磨后的样品用二氯甲烷熏蒸后,发射峰位置又转变为与原始样品几乎一致。再次将其研磨,则又回到第一次研磨后的发射峰位置,说明此类化合物具有典型的压致变色性质。
Claims (2)
1.一类具有聚集诱导发光和压致变色性质的荧光材料,其特征在于该荧光材料的结构式如下所示:
式中Ar代表苯基、C1~C4烷基取代苯基、C1~C4烷氧基取代苯基、4-羟甲基苯基、噻吩基、C1~C4烷基取代噻吩基、呋喃基、羟基取代苯基、卤代苯基、萘基、N-碳酸叔丁酯-2-吡咯基、4-叔丁基二甲基硅氧基苯基中的任意一种。
2.根据权利要求1所述的具有聚集诱导发光和压致变色性质的荧光材料,其特征在于:所述的Ar代表苯基、4-甲基苯基、2-甲基苯基、4-甲氧基苯基、2-甲氧基苯基、2,6-二甲氧基苯基、4-羟甲基苯基、2-噻吩基、5-甲基-2-噻吩基、3-呋喃基、4-羟基苯基、4-氯苯基、4-氟苯基、1-萘基、2-萘基、N-碳酸叔丁酯-2-吡咯基、4-叔丁基二甲基硅氧基苯基中的任意一种。
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CN114478357A (zh) * | 2022-04-15 | 2022-05-13 | 江苏新视界先进功能纤维创新中心有限公司 | 含卤键的压致变色聚集诱导发光分子 |
CN115504930A (zh) * | 2022-09-29 | 2022-12-23 | 合肥工业大学 | 一种具有多重刺激响应的双吡啶基聚集诱导发光化合物及其制备方法和应用 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20120276651A1 (en) * | 2011-04-26 | 2012-11-01 | Korea Institute Of Science And Technology | Fluorescent nanoprobe for detecting hydrogen peroxide and fabrication method thereof |
CN103641743A (zh) * | 2013-12-09 | 2014-03-19 | 浙江工业大学 | 一种三苯乙烯腈衍生物及其制备方法和应用 |
CN105154068A (zh) * | 2015-09-14 | 2015-12-16 | 陕西师范大学 | 基于联二萘酚的聚集诱导发光型手性荧光材料 |
-
2016
- 2016-07-29 CN CN201610612801.2A patent/CN106187817B/zh not_active Expired - Fee Related
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20120276651A1 (en) * | 2011-04-26 | 2012-11-01 | Korea Institute Of Science And Technology | Fluorescent nanoprobe for detecting hydrogen peroxide and fabrication method thereof |
CN103641743A (zh) * | 2013-12-09 | 2014-03-19 | 浙江工业大学 | 一种三苯乙烯腈衍生物及其制备方法和应用 |
CN105154068A (zh) * | 2015-09-14 | 2015-12-16 | 陕西师范大学 | 基于联二萘酚的聚集诱导发光型手性荧光材料 |
Non-Patent Citations (3)
Title |
---|
AUDREY GUERLIN等: "Tunable Optical Properties of Chromophores Derived from Oligo(p-phenylene vinylene)", 《ORG. LETT.》 * |
MASAYUKI TAKADA等: "NOVEL MOLECULAR DESIGN FOR ENHANCED SECOND-ORDER NONLINEAR OPTICAL RESPONSE WITH WIDE TRANSPARENCY: CYANOVINYL AROMATICS", 《MOL. CRYST. LIQ. CRYST.》 * |
MICHELLE S. LIU等: "Effect of Cyano Substituents on Electron Affinity and Electron-Transporting Properties of Conjugated Polymers", 《MACROMOLECULES》 * |
Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
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CN107501170A (zh) * | 2017-08-17 | 2017-12-22 | 陕西师范大学 | 一类光谱可调的聚集诱导发光型荧光材料及其制备方法和应用 |
CN107501170B (zh) * | 2017-08-17 | 2019-08-20 | 陕西师范大学 | 一类光谱可调的聚集诱导发光型荧光材料及其制备方法和应用 |
CN110305114A (zh) * | 2018-03-27 | 2019-10-08 | 武汉尚赛光电科技有限公司 | 一种具有聚集诱导荧光和压致荧光变色性质的蒽基荧光材料及其应用 |
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CN108610381B (zh) * | 2018-04-20 | 2020-07-28 | 南京邮电大学 | 一种基于芴基噁二唑类铱配合物、制备及应用方法 |
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CN111116545A (zh) * | 2020-03-04 | 2020-05-08 | 太原理工大学 | 基于外界刺激解锁的可擦写荧光材料 |
CN112482263A (zh) * | 2020-11-12 | 2021-03-12 | 招商局重庆交通科研设计院有限公司 | 一种超载检测路面及车辆超载检测方法 |
CN114478357A (zh) * | 2022-04-15 | 2022-05-13 | 江苏新视界先进功能纤维创新中心有限公司 | 含卤键的压致变色聚集诱导发光分子 |
CN115504930A (zh) * | 2022-09-29 | 2022-12-23 | 合肥工业大学 | 一种具有多重刺激响应的双吡啶基聚集诱导发光化合物及其制备方法和应用 |
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