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CN116716102A - 基于4-（4-苯乙烯基）苯甲腈荧光染料为基础的防伪应用 - Google Patents

基于4-（4-苯乙烯基）苯甲腈荧光染料为基础的防伪应用 Download PDF

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CN116716102A
CN116716102A CN202310719890.0A CN202310719890A CN116716102A CN 116716102 A CN116716102 A CN 116716102A CN 202310719890 A CN202310719890 A CN 202310719890A CN 116716102 A CN116716102 A CN 116716102A
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房颖
于慧
栾俊钰
季本炀
赵建树
王鲲鹏
胡志强
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Qingdao University of Science and Technology
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Abstract

本发明提供一种基于4‑(4‑苯乙烯基)苯甲腈荧光染料，以4‑氰基溴苄和亚磷酸三乙酯为原料制备磷酸衍生物，再由磷酸衍生物和苯甲醛类化合物合成得到，其结构不同于现有的荧光染料，是一种新型荧光染料，本发明所述的化合物的易于制备，产物收率高且稳定性好，将其中的4‑(4‑二甲氨基苯乙烯基)苯甲腈和4‑(4‑甲基苯乙烯基)苯甲腈或4‑(4‑氰基苯乙烯基)苯甲腈进行一定比例的混合，能够使得混合后的4‑(4‑苯乙烯基)苯甲腈荧光染料发出白色荧光，通过调控两种化合物的混合比例，可实现荧光颜色从蓝色到白色再到黄色的渐变，可用于防伪领域。

Description

基于4-(4-苯乙烯基)苯甲腈荧光染料为基础的防伪应用
技术领域
本发明属于荧光材料技术领域，具体涉及一种4-(4-苯乙烯基)苯甲腈类固体荧光材料在防伪领域的应用。
背景技术
白光为复合光，具有白色荧光的染料分子极为稀有。红色，绿色和蓝色三种原色对于实现白光发射是至关重要的，目前，多数情况为通过合成对比色的荧光染料来对其进行比例的调控以实现白色荧光的呈现。然而，制备两种化学性质稳定且互不影响的新型的对比色的荧光染料本身具备一定难度；再者，两种对比色的荧光染料的调控比例极难把握，进一步通过调节两种染料配比以实现混合物的荧光颜色分别由两种对比色至白色的荧光颜色规律渐变是很新颖且具有挑战性的。
相对于红、绿两种原色，蓝色荧光材料不仅充当蓝光器件材料，还可以充当绿色和红色掺杂剂的主体材料。目前，具备深蓝色荧光发射的固体AIE材料的开发较少。4-(4-苯乙烯基)苯甲腈类化合物通常是由乙烯相连的两个苯环构成的化合物，该类化合物具有典型的共轭结构，改变供电子基团和吸电子基团就可以改变二苯乙烯大π键上电子云分布，从而影响化合物的性质，这有利于通过设计，合成不同对比色的荧光染料，并进一步掺杂不同对比色的荧光染料得到荧光颜色规律变化的荧光材料来达到防伪的目的。
发明内容
本发明提供了一种基于4-(4-苯乙烯基)苯甲腈固体荧光染料及其在防伪方面的潜在应用。
本发明所述的荧光化合物结构简单，易于合成，具有较大的荧光发射波长和高固体荧光量子产率。本发明所述荧光材料具有易于制备、成本低廉、稳定性好、无毒环保等优点，可用于防伪领域。
本发明的技术方案为：
第一方面，本发明提供一种固体荧光染料，具有式I的结构：
其中，R为氢、氟、氯、氰基、二甲氨基、甲氧基或甲基中的至少一种。
上述固体荧光染料的制备反应式如下：
第二方面，本发明提供的荧光材料在溶液状态下(10-5M)荧光较弱，在固体粉末状态下可发出明亮的黄色或蓝色荧光，具有很高的绝对荧光量子产率。
第三方面，本发明还提供一种固体荧光材料的应用，将其进行一定比例掺杂，应用于防伪领域。
第四方面，作为优选，可进行掺杂的两种荧光染料为R为二甲氨基的式I化合物(A)和R为其他取代基(氢、氟、氯、氰基、甲氧基或甲基)的式I化合物(B)，其中最优选为R为二甲氨基的式I化合物和R为甲基或氰基的式I化合物。
第五方面，为实现材料荧光颜色从蓝色到白色再到黄色的渐变，作为优选，A和B的掺杂比例为0.01:1-100:1。
第六方面，在防伪应用中，具体包括如下步骤：
步骤1将制备好的混合荧光染料添加到防伪标签等防伪产品中；
步骤2用紫外光源照射防伪产品，按一定比例混合的荧光染料会呈现有规律的荧光颜色渐变。
具体地，紫外光源照射在波长为250～430nm的光照条件下进行。
本发明具有以下优点：
(1)本发明提供的固体荧光材料制备方法简单、具有优良的荧光性能、稳定性好、无毒环保。
(2)本发明中的防伪应用方法操作简便、识别效率高。
附图说明
图1为实施例5中由4-(4-二甲氨基苯乙烯基)苯甲腈和4-(4-氰基苯乙烯基)苯甲腈进行掺杂制备的固体荧光材料在日光及紫外光照下的荧光照片；
图2为实施例5中由4-(4-二甲氨基苯乙烯基)苯甲腈和4-(4-甲基苯乙烯基)苯甲腈进行掺杂制备的固体荧光材料在日光及紫外光照下的荧光照片。
图3为实施例5中由4-(4-二甲氨基苯乙烯基)苯甲腈和4-(4-氰基苯乙烯基)苯甲腈或4-(4-甲基苯乙烯基)苯甲腈进行掺杂制备的固体荧光材料在紫外光照下的渐变荧光颜色变化CIE坐标图。
具体实施方式
下面将结合本发明实施例中的附图，对本发明实施例中的技术方案进行清楚、完整地描述，显然，所描述的实施例仅是本发明一部分实施例，而不是全部的实施例。基于本发明中的实施例，本领域普通技术人员所获得的所有其他实施例，都属于本发明保护的范围。
实施例1
制备4-(4-二甲氨基苯乙烯基)苯甲腈荧光染料：
将4-氰基溴苄和亚磷酸三乙酯加入100mL单口瓶中，在130℃的回流搅拌条件下反应2小时，制备磷酸衍生物，然后加入4-二甲氨基苯甲醛(1.0mmol)并在室温下搅拌反应12小时，TLC监测反应进程。当反应完全后，使用冰水(10mL)淬灭反应。混合溶液用乙酸乙酯(10mL)萃取，用饱和NaCl溶液(20mL)洗涤，收集有机层，溶液经Na2SO4干燥后，真空蒸发溶剂。最后再通过乙酸乙酯重结晶,得到黄色固体化合物4-(4-二甲氨基苯乙烯基)苯甲腈。产率:89％.1H NMR(500MHz,CDCl3)δ7.63(d,J＝8.4Hz,2H),7.56(d,J＝8.2Hz,2H),7.47(d,J＝8.8Hz,2H),7.19(d,J＝16.2Hz,1H),6.92(d,J＝16.2Hz,1H),6.78–6.72(m,2H),3.05(s,6H).13C NMR(126MHz,CDCl3)δ149.65,141.82,131.58,131.35,127.15,125.17,123.37,120.99,118.36,111.17,108.18,39.28.
实施例2
制备4-(4-氰基苯乙烯基)苯甲腈荧光染料：
将4-氰基溴苄和亚磷酸三乙酯加入100mL单口瓶中，在130℃的回流搅拌条件下反应2小时，制备磷酸衍生物，然后加入4-氰基苯甲醛(1.0mmol)并在室温下搅拌反应12小时，TLC监测反应进程。当反应完全后，使用冰水(10mL)淬灭反应。混合溶液用乙酸乙酯(10mL)萃取，用饱和NaCl溶液(20mL)洗涤，收集有机层，溶液经Na2SO4干燥后，真空蒸发溶剂。最后再通过乙酸乙酯重结晶,得到白色固体化合物4-(4-氰基苯乙烯基)苯甲腈。产率:89％.熔点:272–274℃.1H NMR(500MHz,DMSO d6)d 7.88(d,J＝8.4Hz,4H),7.84(d,J＝8.5Hz,4H),7.56(s,2H).13C NMR(126MHz,DMSO d6)d141.1,132.7,130.4,127.6,118.9,110.3.HRMS(ESI)calcd.for C16H10N2Na[M+Na]+:253.0736,found:253.0739.
实施例3
制备4-(4-甲基苯乙烯基)苯甲腈荧光染料：
将4-氰基溴苄和亚磷酸三乙酯加入100mL单口瓶中，在130℃的回流搅拌条件下反应2小时，在制备出的磷酸衍生物中，加入4-甲基苯甲醛(1.0mmol)，在室温条件下继续搅拌12小时，TLC监测反应进程。反应完全后，使用冰水(10mL)淬灭反应。混合溶液用乙酸乙酯(10mL)萃取，用饱和NaCl溶液(20mL)洗涤,收集有机层，溶液经Na2SO4干燥后，真空蒸发溶剂。粗产物以石油醚和乙酸乙酯为洗脱溶剂(PE:EA＝12:1)经硅胶柱纯化。最后得到白色固体化合物。产率:84％.熔点:177–178℃.1H NMR(500MHz,CDCl3)d 7.66(d,J＝8.4Hz,2H),7.60(d,J＝8.4Hz,2H),7.50–7.44(m,2H),7.20–7.26(m,3H),7.08(d,J＝16.3Hz,1H),2.42(s,3H).13C NMR(126MHz,CDCl3)d 141.0,137.7,132.5,131.4,131.3,128.5,125.8,125.7,124.7,118.1,109.2.HRMS(ESI)calcd.for C16H14N[M+H]+:220.1121,found:220.1119.
实施例4
对实施例1-3制备的荧光染料分子的紫外吸收和荧光发射等光学性能进行研究。
将荧光染料分子4-(4-二甲氨基苯乙烯基)苯甲腈、4-(4-氰基苯乙烯基)苯甲腈、4-(4-甲基苯乙烯基)苯甲腈溶于DMSO溶液中，分别配制浓度为10-5M的待测溶液。通过紫外吸收和荧光测试，发现荧光染料分子4-(4-二甲氨基苯乙烯基)苯甲腈、4-(4-氰基苯乙烯基)苯甲腈、4-(4-甲基苯乙烯基)苯甲腈在DMSO溶液中的最大吸收波长分别为393nm、334nm和332nm，最大荧光发射波长为539nm、379nm和399nm。在固体状态下，荧光染料分子4-(4-二甲氨基苯乙烯基)苯甲腈受激发后可发出明亮的黄色荧光，其荧光发射波长为510nm，固态荧光量子产率达到14％，4-(4-氰基苯乙烯基)苯甲腈和4-(4-甲基苯乙烯基)苯甲腈受激发后可发出明亮的蓝色荧光，其最大荧光发射波长为439nm和420nm，固体荧光量子产率分别高达46.35％和63.90％。
实施例5
将实施例1制备的荧光染料分子分别与实施例2和3制备的荧光染料分子进行掺杂，制备混合固体荧光材料。通过调节荧光染料分子4-(4-二甲氨基苯乙烯基)苯甲腈和4-(4-氰基苯乙烯基)苯甲腈或4-(4-甲基苯乙烯基)苯甲腈的摩尔比0.01:1-100:1，发现可实现固体荧光由蓝色至白色再至黄色的渐变。

Claims (4)

1.一种用于防伪的4-(4-苯乙烯基)苯甲腈的荧光染料，其特征在于，具有式I的结构：
其中，R为氢、氟、氯、氰基、二甲胺基、甲氧基或甲基中的一种。
2.根据权利要求1所述的防伪应用荧光材料，其特征在于R为二甲胺基的式I化合物和R为甲基或氰基的式I化合物，两者的摩尔比为0.01:1-100:1。
3.根据权利要求1所述的荧光染料的应用，其特征在于，应用于防伪识别中，具体包括如下步骤：
步骤1将制备好荧光染料粉末按一定比例混合好，添加在防伪材料中；
步骤2在日光下，防伪材料中的荧光染料颜色均一，而用紫外光源照射荧光材料，呈现有规律的颜色渐变。
4.根据权利要求3所述的荧光染料的应用，其特征在于，紫外光源照射在波长为250～430nm的光照条件下进行。
CN202310719890.0A 2023-06-17 2023-06-17 基于4-（4-苯乙烯基）苯甲腈荧光染料为基础的防伪应用 Pending CN116716102A (zh)

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