CN111320647A - 一种硅烷桥联发光材料及其制备方法、应用和显色剂 - Google Patents
一种硅烷桥联发光材料及其制备方法、应用和显色剂 Download PDFInfo
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- CN111320647A CN111320647A CN202010290469.9A CN202010290469A CN111320647A CN 111320647 A CN111320647 A CN 111320647A CN 202010290469 A CN202010290469 A CN 202010290469A CN 111320647 A CN111320647 A CN 111320647A
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- 239000000463 material Substances 0.000 title claims abstract description 74
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 title claims abstract description 30
- 229910000077 silane Inorganic materials 0.000 title claims abstract description 29
- 238000002360 preparation method Methods 0.000 title abstract description 20
- 238000000034 method Methods 0.000 claims abstract description 24
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 18
- YMJNWNGWIIFMDE-UHFFFAOYSA-N trifluoromethylsulfonylsilane Chemical compound FC(F)(F)S([SiH3])(=O)=O YMJNWNGWIIFMDE-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000005046 Chlorosilane Substances 0.000 claims abstract description 8
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical compound Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 claims abstract description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 40
- 238000006243 chemical reaction Methods 0.000 claims description 25
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 22
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical group [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 21
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 9
- 229910052744 lithium Inorganic materials 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 claims description 7
- JZALIDSFNICAQX-UHFFFAOYSA-N dichloro-methyl-trimethylsilylsilane Chemical compound C[Si](C)(C)[Si](C)(Cl)Cl JZALIDSFNICAQX-UHFFFAOYSA-N 0.000 claims description 6
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- PBCJIPOGFJYBJE-UHFFFAOYSA-N acetonitrile;hydrate Chemical compound O.CC#N PBCJIPOGFJYBJE-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
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- BLHLJVCOVBYQQS-UHFFFAOYSA-N ethyllithium Chemical compound [Li]CC BLHLJVCOVBYQQS-UHFFFAOYSA-N 0.000 claims description 2
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
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- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene chloride Substances ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 13
- 239000007787 solid Substances 0.000 description 13
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 10
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- 229910008045 Si-Si Inorganic materials 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- 229910006411 Si—Si Inorganic materials 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
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- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
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- 229920000548 poly(silane) polymer Polymers 0.000 description 4
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- JLZUZNKTTIRERF-UHFFFAOYSA-N tetraphenylethylene Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)=C(C=1C=CC=CC=1)C1=CC=CC=C1 JLZUZNKTTIRERF-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
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- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 3
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- 230000001680 brushing effect Effects 0.000 description 2
- KWYZNESIGBQHJK-UHFFFAOYSA-N chloro-dimethyl-phenylsilane Chemical compound C[Si](C)(Cl)C1=CC=CC=C1 KWYZNESIGBQHJK-UHFFFAOYSA-N 0.000 description 2
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- PBCKWRAUOUBELJ-UHFFFAOYSA-N C[Si](C)(C)[Si](C)(C)[Si](C)(C)[Si](C)(S(C(F)(F)F)(=O)=O)S(C(F)(F)F)(=O)=O Chemical compound C[Si](C)(C)[Si](C)(C)[Si](C)(C)[Si](C)(S(C(F)(F)F)(=O)=O)S(C(F)(F)F)(=O)=O PBCKWRAUOUBELJ-UHFFFAOYSA-N 0.000 description 1
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- OPODDPFUNXAJMM-UHFFFAOYSA-N bis(trifluoromethylsulfonyl)-bis(trimethylsilyl)silane Chemical compound C[Si]([Si]([Si](C)(C)C)(S(=O)(=O)C(F)(F)F)S(=O)(=O)C(F)(F)F)(C)C OPODDPFUNXAJMM-UHFFFAOYSA-N 0.000 description 1
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- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
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- VEDJZFSRVVQBIL-UHFFFAOYSA-N trisilane Chemical compound [SiH3][SiH2][SiH3] VEDJZFSRVVQBIL-UHFFFAOYSA-N 0.000 description 1
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- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/0805—Compounds with Si-C or Si-Si linkages comprising only Si, C or H atoms
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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
- C07F7/0814—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring is substituted at a C ring atom by Si
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- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/0825—Preparations of compounds not comprising Si-Si or Si-cyano linkages
- C07F7/0827—Syntheses with formation of a Si-C bond
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Abstract
Description
技术领域
本发明涉及检测技术领域,具体涉及一种硅烷桥联发光材料及其制备方法、应用和显色剂。
背景技术
有机聚硅烷是指主链为直接相连Si-Si原子,硅原子上带有R基的化合物。早在20世纪中叶,Gilman等人观察到低聚硅烷与其结构类似物烷烃的电子性质显著不同。烷烃在190nm以上没有吸收,而低聚硅烷在200~300nm处显示强吸收。这是由于聚硅烷主链的σ电子能够沿着Si-Si主链离域,获得类似于π共轭效应的σ共轭效应,这种共轭效应使聚硅烷显示出能隙为3~4eV的半导体行为。
在主链上引入π共轭单元可通过σ-π共轭作用使聚合物具有独特的光电性能,在有机发光二极管、发光材料、光学传感器以及耐热材料等领域具有广泛的潜在应用。更为重要的是,硅原子可增加有机发光材料的生物相容性,拓展其在生物领域的应用。
指纹具有因人而异、终生不变、触物留痕的特点,被公认为司法界的证据之首。指纹鉴定即指纹识别,是以指、掌乳突线花纹特征为依据识别个人。指纹技术中最关键的问题是潜在指纹的显现技术。指纹显现技术发展至今已有上百年的历史,不仅出现了刷粉法、熏显法、茚三酮法等实际案检中常用的方法,而且近些年来发展了很多分析检测技术用于指纹检测,如质谱法、红外光谱法、纳米粒子法等。含硅材料也在指纹显示技术中有较多研究。
CN 102920462 A公开了表面功能化的纳米上转换材料用于潜在指纹的显现,对纳米上转换材料进行碱化处理、氨基硅烷化修饰、醛基化修饰、用粉末法或悬浮液法对不同客体表面的潜在指纹进行显现,醛基与潜在指纹中的氨基酸残基反应,通过化学偶联沉积在指纹纹线上,在980nm红外光照射下发出可见的有色荧光,从而能够清晰地显现出客体表面的潜在指纹。
CN102988058A公开了一种用于潜指纹显示的的彩色二氧化硅纳米粒子及其制备方法,该彩色二氧化硅纳米粒子是通过三取代硅烷结合水溶性染料并包覆在纳米二氧化硅粒子表面而形成的,粒径小,用于潜指纹显示具有很好的灵敏度,制备方法简便,成本较低,易于操作。
但这些方法都存在各自的缺点,如最常用的刷粉法的小粒度粉尘、某些有致癌作用的荧光染料及熏显法物质分解反应产生的有毒气体均会对检测人员的身体健康造成严重危害,而质谱法会破坏指纹的原始状态,不能用于重复测定。因而,开发简单、快速、适用范围广、容易操作的新方法对潜指纹进行显现依然是亟待解决的技术问题。
发明内容
本发明旨在提供一种低聚硅烷桥联的发光材料,这类发光材料具有较高的光稳定性,发光效率强,基本保留发光团的原始颜色,且由于硅烷结构能够显著提高材料的亲脂性,促进发光材料与皮脂结合力,实现快速高分辨率的潜指纹可视化成像。
为实现上述目的,本发明采用的技术方案是:
一种硅烷桥联发光材料,具有如式(I)所示的结构式:
其中,n为1~20的自然数;R1为共轭发光基团,具有如式a~f所示结构式中任一种;
其中,R2为氢原子或烷基链,n为1~20的自然数。
本发明通过在发光材料上桥联不同长度的硅烷链,利用低聚硅烷中Si-Si键与共轭发光基团的σ-π共轭效应,增强发光材料的光热稳定性。聚硅烷链的引入阻碍了两个相邻共轭发光基团之间的紧密分子间接触,从而增强了固态发射,这类发光材料具有较高的光稳定性,发光效率强,并几乎保留了发光基团的原始颜色。
所述的烷基链为碳原子1~20的直链、支链或环状烷基链,烷基链上一个或多个碳原子被氧原子、烯基、炔基、芳基、羰基、羟基、氨基、羧基、硝基或酯基取代。
优选地,一种硅烷桥联发光材料,具有如式(II)所示的结构式:
其中,n为1~20的自然数。该结构为对称结构,易于合成,在有机结构中,Si-Si一维链具有电子离域、结构易于转动的特点。因此,烷链作为桥联一方面由于空间位阻增大可以有效减少共轭发光团的堆积作用,从而增强样品的发光效率;另一方面可以增加亲脂性,使材料易于和潜指纹中的油脂结合,提高发光成像的亮度。
本发明还公开了所述的硅烷桥联发光材料的制备方法,包括如下步骤:
步骤1:将化合物A经锂化试剂锂化获得化合物A的锂化物;
步骤2:将化合物A的锂化物与氯硅烷或三氟甲磺酰硅烷反应,得到所述的硅烷桥联发光材料;
化合物A具有a’~f’所示的任一种结构式:
其中X为卤素。
优选的,所述的化合物A具有a’所示的结构式,对应所制备的硅烷桥联发光材料的过程反应方程式如下:
本发明通过低聚硅烷调控分子结构的设计策略提供了一种简单的方法来构建新型发光材料,该制备方法步骤简单、产率高,制得的发光材料纯度高,光学性能稳定。
步骤1中,所述的锂化试剂为正丁基锂、乙基锂、苯基锂、甲基锂或锂,所述锂化试剂与化合物A的摩尔比为1.5~1:1,反应溶剂为四氢呋喃或乙醚,反应温度为-80~-10℃,反应时间为2~5h。
优选地,所述的锂化试剂为正丁基锂,商业化的正丁基锂易于采购,价格低廉,与卤代发光团的摩尔比不宜大于1.5:1,锂化试剂小于1时,卤代发光团的锂化不充分,锂化试剂过多时,残留的锂化试剂与后续加入的硅烷反应,影响硅烷与锂化发光团的反应。所述的反应温度-80~-10℃利于完全锂化,反应时间不宜过长,否则锂化发光团有分解的可能。
步骤2中所述的化合物A的锂化物与氯硅烷或三氟甲磺酰硅烷的摩尔比为1.5~1:1,反应溶剂为四氢呋喃或乙醚,反应温度为-80~0℃,反应时间为6~12h。因锂化发光团不稳定,反应应在低温下进行,且锂化发光团的用量要不少于硅烷,反应效率才更高。
优选地,步骤2中所述的氯硅烷包括二氯二甲基硅烷或二氯四甲基乙硅烷。当所制备的产物式(I)中n大于等于3时,商品化的氯硅烷已不易购买且定制成本较高,因此采用易于制备的三氟甲磺酰硅烷作为反应原料,并且OTf(三氟甲磺酸基)是比氯更好的离去基团,有利于反应的高效进行。
所述的三氟甲磺酰硅烷具有式(III)所示的结构式:
其中,n为1~20的自然数。
当所述的硅烷桥联发光材料中n大于等于3时,优选地,步骤2中化合物A的锂化物与三氟甲磺酰硅烷反应,得到所述的硅烷桥联发光材料。
所述的三氟甲磺酰硅烷的制备过程包括如下步骤:
当n≥3时,由二氯二甲基硅烷和二氯四甲基二硅烷为原料制得含3个和4个硅的三氟甲磺酰基硅烷,再以此为原料继续制备n≥5的三氟甲磺酰基硅烷。
本发明还公开一种显色剂,包括权利要求1~3任一项所述的硅烷桥联发光材料和乙腈水溶液混合溶剂;其中所述的硅烷桥联发光材料的浓度为100~300mg/L;乙腈水溶液中乙腈的体积分数为30~50%。该显色剂可用于潜指纹的可视化成像。
本发明的硅烷桥联发光材料中的硅烷结构有助于提高发光材料的亲脂性,可快速与潜在指纹的残留油脂结合,使其成为快速,易于操作和高分辨率指纹可视化成像的极佳候选者。
所述的硅烷桥联发光材料在潜指纹显示中的应用,将所述的硅烷桥发光材料制备成显色剂,向潜指纹区域溶液喷涂,经荧光显色即可简易、快速的获得潜指纹的高分辨率可视化图像。
与现有技术相比,本发明具有以下有益效果:
(1)本发明利用低聚硅烷桥联形成的σ-π共轭效应可细微调控发光材料的发射波长,同时增强发光材料的发光效率,光热稳定性和亲脂性。
(2)本发明的硅烷桥联发光材料制备方法简单、产率高,制得的发光材料纯度高,光学性能稳定。
(3)本发明所得到的低聚硅烷桥联发光材料,展现出高效高分辨的潜指纹成像。
附图说明
图1为实施例1~4制备的发光材料紫外吸收光谱图;
图2为实施例1~4制备的发光材料固体荧光发射光谱图;
图3为应用例1的过程示意图;
图4为应用例1获得的潜在指纹可视化成像图。
具体实施方式
为了使本发明的目的、技术方案及优点更加清楚明白,以下结合实施例,对本发明进行进一步详细说明。应当理解,此处所描述的具体实施例仅仅用以解释本发明,并不用于限定本发明。本领域技术人员在理解本发明的技术方案基础上进行修改或等同替换,而未脱离本发明技术方案的精神和范围,均应涵盖在本发明的保护范围内。
实施例1
单硅烷桥联的双四苯基乙烯发光材料(BTPE-Si1)的制备
反应方程式:
(1)中间体a”按照文献(Chem.Commun.,2014,50,1725-1727.)报道的方法制备。
(2)在氩气保护下,将中间体a”(300mg,0.73mmol)和20mL无水THF加入100mLSchlenk瓶中。冷却至-78℃。将正丁基锂溶液(0.5mL,0.8mmol,1.6M的正己烷溶液)滴加到烧瓶中,反应混合物在-78℃下搅拌3h,之后滴加二氯二甲基硅烷(44μL,0.36mmol)。加完之后,将混合物缓慢升温至室温并搅拌2小时,反应结束将混合物加入到NaHCO3水溶液中,用CH2Cl2萃取有机相,经无水Na2SO4干燥,并减压旋蒸除去溶剂。粗产物通过层析硅胶柱纯化,(CH2Cl2/PE=1/10)作为洗脱剂,得到白色粉末产物,产率为49%(129mg)。
1H NMR(400MHz,CD2Cl2)δ7.20(d,4H),7.12-7.08(m,18H),7.05-6.99(m,16H),0.44(s,6H).13C NMR(100MHz,CDCl3)δ144.41,143.90,143.81,141.28,141.10,136.31,133.61,131.49,130.63,127.76,126.54,-2.23.HRMS-ESI:m/z:calcd for[C54H44Si+Na]+:743.3110.Found:743.3104.
实施例2
双硅烷桥联的双四苯基乙烯发光材料(BTPE-Si2)的制备
反应方程式:
在氩气保护下,将中间体a”(300mg,0.73mmol)和20mL无水THF加入100mL Schlenk瓶中。冷却至-78℃。将正丁基锂溶液(0.5mL,0.8mmol,1.6M的正己烷溶液)滴加到烧瓶中,反应混合物在-78℃下搅拌3h,之后滴加二氯四甲基乙硅烷(64μL,0.36mmol)。加完之后,将混合物缓慢升温至室温并搅拌2小时,反应结束将混合物加入到NaHCO3水溶液中,用CH2Cl2萃取有机相,经无水Na2SO4干燥,并减压旋蒸除去溶剂。粗产物通过层析硅胶柱纯化,(CH2Cl2/PE=1/10)作为洗脱剂,得到白色粉末产物,产率为45%(128mg)。
1H NMR(400MHz,CDCl3)δ7.10-7.00(m,30H),6.96-6.89(m,8H),0.44(s,12H).13CNMR(100MHz,CDCl3)δ143.93,143.90,143.80,141.26,141.13,136.85,133.23,131.50,131.47,130.59,127.77,127.73,126.54,-4.38.HRMS-ESI:m/z:calcd for[C56H50Si2+Na]+:801.3349.Found:801.3343.
实施例3
三硅烷桥联的双四苯基乙烯发光材料(BTPE-Si3)的制备
反应方程式:
(1)制备二(三氟甲磺酰基)六甲基三硅烷5a:
在0℃下,将金属锂(5.0g,714mmol,使用前用己烷洗涤)加入THF(100mL)中,慢慢滴加氯二甲基苯基硅烷2(15mL,89mmol),将混合物在0℃搅拌过夜。在装有滴液漏斗的烧瓶中,将二氯二甲基硅烷(5.4mL,44.5mmol)溶于THF(150mL)中,冷却至0℃。用注射器将深红色的苯基二甲基甲硅烷基锂3溶液转移到滴液漏斗中,之后慢慢滴加到二氯二甲基硅烷溶液中,用时5分钟。加完之后,将反应混合物升温至室温,搅拌过夜。反应结束后,减压除去THF,之后加入乙醚(100mL)。过滤除去沉淀的氯化锂,并将乙醚溶液真空浓缩。通过柱色谱法纯化,得到无色油状物4a(10.20g,70%)。
(2)制备三硅烷桥联的双四苯基乙烯发光材料(BTPE-Si3):
在氩气下,于-78℃将正丁基锂(1.4mL,2.2mmol,1.6M的正己烷溶液)滴加到中间体1(820mg,2mmol)的THF(40mL)溶液中,继续搅拌1小时,之后将温度升至-60℃,并继续搅拌30分钟。得到TPE-锂试剂,备用。
在0℃下向4a(328mg,1mmol)的甲苯(5mL)溶液中加入三氟甲磺酸(228μL,2.4mmol)。搅拌20分钟,然后冷却至-78℃。将三氟甲硅烷基甲硅烷溶液滴加到TPE-锂试剂溶液中。在-78℃下搅拌过夜后,升温至室温继续搅拌6小时。加入饱和NH4Cl溶液(10mL),混合物用DCM(3×30mL)萃取,合并的有机层经Na2SO4干燥并真空浓缩。通过柱色谱法(PE/DCM=10:2)纯化,得到白色固体产物,产率为70%(586mg)。
1H NMR(400MHz,CD2Cl2)δ7.11-7.01(m,33H),6.92(d,5H),0.16(s,12H),0.02(s,6H).13C NMR(100MHz,CDCl3)δ143.97,143.91,143.80,141.18,141.07,137.75,133.19,131.54,131.49,131.46,130.72,127.84,127.75,126.51,-3.35,-6.43.HRMS-ESI:m/z:calcd for[C58H56Si3+Na]+:859.3588.Found:859.3582.
实施例4
四硅烷桥联的双四苯基乙烯发光材料(BTPE-Si4)的制备
反应方程式:
制备二(三氟甲磺酰基)八甲基四硅烷5b:
在0℃下,将金属锂(5.0g,714mmol,使用前用己烷洗涤)加入THF(100mL)中,慢慢滴加氯二甲基苯基硅烷(15mL,89mmol),将混合物在0℃搅拌过夜。在装有滴液漏斗的烧瓶中,将二氯四甲基二硅烷(8.3g,44.5mmol)溶于THF(150mL)中,冷却至0℃。用注射器将深红色的苯基二甲基甲硅烷基锂溶液转移到滴液漏斗中,之后慢慢滴加到二氯二甲基硅烷溶液中,用时4小时。加完之后,将反应混合物升温至室温,搅拌过夜。反应结束后,减压除去THF,之后加入乙醚(100mL)。过滤除去沉淀的氯化锂,并将乙醚溶液真空浓缩。通过柱色谱法纯化,得到无色油状物4b(11.20g,75%)。
在氩气下,于-78℃将正丁基锂(1.4mL,2.2mmol,1.6M的正己烷溶液)滴加到中间体1(820mg,2mmol)的THF(40mL)溶液中,继续搅拌1小时,之后将温度升至-60℃,并继续搅拌30分钟。得到TPE-锂试剂,备用。
在0℃下向4b(387mg,1mmol)的甲苯(5mL)溶液中加入三氟甲磺酸(228μL,2.4mmol)。搅拌20分钟,然后冷却至-78℃。将三氟甲硅烷基甲硅烷溶液滴加到TPE-锂试剂溶液中。在-78℃下搅拌过夜后,升温至室温继续搅拌6小时。加入饱和NH4Cl溶液(10mL),混合物用DCM(3×30mL)萃取,合并的有机层经Na2SO4干燥并真空浓缩。通过柱色谱法(PE/DCM=10:2)纯化,得到白色固体产物,产率为55%(492mg)。
1H NMR(400MHz,CD2Cl2)δ7.16(d,J=8Hz,4H),7.12-7.07(m,18H),7.02(dd,12H),6.97(d,J=8Hz,4H),0.29(s,12H),-0.07(s,12H).13C NMR(100MHz,CDCl3)δ143.98,143.91,143.88,143.80,141.17,141.09,137.88,133.13,131.54,131.50,131.48,130.75,127.80,127.76,126.51,-3.05,-5.53.HRMS-ESI:m/z:calcd for[C60H62Si4+Na]+:917.3826.Found:917.3821.
实施例5
三硅烷桥联的双咔唑发光材料(BCz-Si3)的制备反应方程式:
向干燥的,并经过氩气抽换气后的反应瓶中加入1,1,2,2,3,3-四甲基-1,3-二苯基三硅烷(4a,328mg,1mmol)和无水甲苯(5mL),0℃搅拌20min后滴加三氟甲磺酸(228μL,2.4mmol)并搅拌0.5h得到5a。
另向干燥的100mL Schlenk反应管中,加入化合物溴代咔唑Cz-Br(500mg,1.92mmol),抽换氩气三次,并在氩气保护下加入无水四氢呋喃(THF,15mL),待化合物1全部溶解后转移至低温槽内降温至-78℃,再向其中缓慢滴加正丁基锂(n-BuLi,1.32mL,2.11mmol,1.1eq,1.6M的正己烷溶液),-78℃搅拌1h后升温至-60℃。加入5a,再搅拌1h后,升温至-50℃搅拌过夜。反应结束后用饱和氯化铵溶液淬灭。二氯甲烷萃取,滤液用无水Na2SO4干燥。所得粗产品用200-300目硅胶粉进行柱层析分离(洗脱剂:石油醚)提纯。得到产物BCz-Si3白色固体粉末色(502mg,49%)。
1H NMR(500MHz,DMSO-d6)δ8.09(s,2H),8.04(d,J=7.7Hz,2H),7.56(d,J=8.2Hz,2H),7.49(d,J=8.1Hz,2H),7.43(m,4H),7.19-7.11(m,2H),3.80(m,6H),0.35(s,12H),0.11(s,6H).13C NMR(126MHz,DMSO-d6)δ=141.01,140.48,130.78,127.07,125.66,125.39,121.92,121.75,120.05,118.82,109.07,108.78,28.88,-2.42,-5.54ppm.HRMScalcd.For C32H38N2NaSi3[M+Na]+:557.2235,found:557.2250.
性能测试
对实施例1、实施例2、实施例3和实施例4制得的如式BTPE-Si1、BTPE-Si2、BTPE-Si3和BTPE-Si4所示的低聚硅烷基桥联的双四苯基乙烯发光材料在四氢呋喃和固体粉末中的的光谱性质检测,结果如表1所示。
表1实施例1~4制备的发光材料的光物理参数
其中,λabs a指发光材料在四氢呋喃溶液中最大吸收波长;λabs b指发光材料在90%(体积分数)水和四氢呋喃混合溶液中最大吸收波长;λem c指发光材料在90%(体积分数)水和四氢呋喃混合溶液中的最大发射波长;λem d指发光材料固体粉末的最大发射波长;QY指发光材料固体粉末的荧光量子产率;τ指固体样品的荧光寿命;CIE(x,y)为发光材料固体粉末的CIE(国际照明委员会)坐标。
实施例1~4制备的发光材料和四苯乙烯(TPE)的紫外吸收光谱图如图1所示,硅烷桥联使材料在溶液中的吸收光谱红移9~17nm,在聚集态的发光红移仅6~10nm。实施例1~4制备的发光材料和TPE的固体荧光发射光谱图如图2所示,其中TPE分子的固态发光在449nm,CIE坐标为(0.14,0.07),为标准的蓝光发射材料,而固体发光效率只有25.0%。含本发明实施例1~4制备的有低聚硅烷桥联的分子BTPE-Si1~BTPE-Si4的固态发光效率明显提高1.6~2.8倍。其中BTPE-Si4的固体发光在457nm,CIE坐标为(0.14,0.13),非常接近TPE的发光,但是发光效率明显提高了2.4倍。
应用例1
指纹样本的收集:指纹来自于23~35岁的志愿者。他们用肥皂彻底洗净双手后,将指尖在鼻子和额头上轻轻摩擦,然后以最小的压力将右手拇指或食指压在不同的表面上。
(1)显色剂溶液的制备:将BTPE-Si3粉末样品溶解在乙腈溶液中,加水配制水的体积分数为30%的H2O-CH3CN溶液,其中BTPE-Si3的浓度为0.25mM(215mg/L)。
(2)指纹显现:取上述BTPE-Si3显色剂溶液逐滴滴到基材表面的指纹上,完全覆盖指纹之后,在环境条件下静置约30秒(孵育时间)。之后,用蒸馏水将基板上多余的显色剂冲去,并用自然风将基材吹干。图3所示为上述过程示意图。
(3)图像采集:用365nm紫外灯照射指纹,使用数码相机对显影的指纹进行拍照采集图像,图像如图4所示,指纹图像清晰可见,放大可观察到一级和二级细节信息。可见本发明的发光材料在潜指纹显示中展现出高效高分辨的潜指纹成像效果。
Claims (10)
2.根据权利要求1所述的硅烷桥联发光材料,其特征在于,所述的烷基链为碳原子1~20的直链、支链或环状烷基链,烷基链上一个或多个碳原子被氧原子、烯基、炔基、芳基、羰基、羟基、氨基、羧基、硝基或酯基取代。
5.根据权利要求4所述的硅烷桥联发光材料的制备方法,其特征在于,步骤1中,所述的锂化试剂为正丁基锂、乙基锂、苯基锂、甲基锂或锂,所述锂化试剂与化合物A的摩尔比为1.5~1:1,反应溶剂为四氢呋喃或乙醚,反应温度为-80~-10℃,反应时间为2~5h。
6.根据权利要求4所述的硅烷桥联发光材料的制备方法,其特征在于,步骤2中,所述的化合物A的锂化物与氯硅烷或三氟甲磺酰硅烷的摩尔比为1.5~1:1,反应溶剂为四氢呋喃或乙醚,反应温度为-80~0℃,反应时间为6~12h。
7.根据权利要求4所述的硅烷桥联发光材料的制备方法,其特征在于,步骤2中,所述的氯硅烷包括二氯二甲基硅烷或二氯四甲基乙硅烷。
9.一种显色剂,其特征在于,包括权利要求1~3任一项所述的硅烷桥联发光材料和乙腈水溶液混合溶剂;其中所述的硅烷桥联发光材料的浓度为100~300mg/L;乙腈水溶液中乙腈的体积分数为30~50%。
10.根据权利要求1~3任一项所述的硅烷桥联发光材料在潜指纹显示中的应用。
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