CN116855100A - 一种可直接用于潜在指纹显影的三苯胺染料及其制备方法和应用 - Google Patents
一种可直接用于潜在指纹显影的三苯胺染料及其制备方法和应用 Download PDFInfo
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Abstract
本发明提供一种可直接用于潜在指纹显影的三苯胺染料,以三苯胺、对氰基溴芐和亚磷酸三乙酯为原料合成,其结构与现已有荧光染料不同,是一种可直接用于潜在指纹显影的三苯胺染料,本发明通过简单的工艺流程,高产率地生产毒性小且结构稳定的可直接用于潜在指纹显影的三苯胺染料,所制备化合物可被直接应用为荧光指纹显影粉,实现潜在指纹清晰显影。该指纹显影粉抗干扰性高、分辨率高、对比度高且显影实时,可被应用于多种材料及复杂的刑事侦查环境。
Description
技术领域
本发明属于荧光染料技术领域,具体涉及一种可直接用于潜在指纹显影的三苯胺染料及其制备方法和应用。
背景技术
现使用的指纹显影技术主要可分为物理显影法和化学显影法,物理显影法主要使用荧光粉或者磁性粉,粉末与指纹中生物残留物如油酸、氨基酸等之间的静电吸附来实现,该方法操作简单,无显影延时,但传统用于指纹显影的磁粉大多是微米级,分散性较差,易团聚。化学显影法包括碘蒸汽法、硝酸银法等方法,主要依靠指纹中残留的有机物与所用化学物质发生反应,这类方法显影更稳定,但是存在显影较慢、毒性较高以及对比度较差等痛点。因此,目前使用的指纹显影技术存在亟待解决的问题。
目前市售的指纹粉在有静电或凹凸不平的基底材料上残留的指纹难以实现高分辨率显影,达不到刑事侦查对指纹提取的要求。三苯胺指纹粉指纹显影法在众多方法中脱颖而出,成为目前刑事案件侦查很受欢迎的潜指纹显影手段。
发明内容
本申请实例提供一种可直接用于潜在指纹显影的三苯胺染料及其制备方法和应用,其组成与现已有荧光染料不同,是一种不需要载体的荧光染料,可直接作为指纹粉使用。本发明以简单的制备流程,高产率地生产出稳定性高且毒性小的三苯胺染料,将所得三苯胺染料直接应用于指纹显影,可与潜在指纹中残留的生物油脂发生响应,在紫外365nm照射下显现出黄色荧光。因此该三苯胺荧光染料可高抗干扰性、高生物相容性,可以高分辨、高对比度、强抗干扰、实时地使潜指纹显影成像,适用于多种基底及复杂的刑事侦查环境。
本发明的技术方案为:
第一方面,本发明提供一种可直接用于潜在指纹显影的三苯胺染料,具有式I的结构:
第二方面,本发明还提供一种三苯胺染料的制备方法,具体包括以下步骤
步骤1,0℃下,POCl3和DMF逐滴混合并搅拌15min,三苯胺加至体系中,将混合物加热130℃,反应45min,冷却至室温倒入冰水进行搅拌,用饱和碳酸氢钠水溶液将pH值调节到6~7,用乙酸乙酯萃取后柱色谱分离得到N,N-二(4-甲酰苯基)苯胺;
步骤2,对氰基溴苄和亚磷酸三乙酯混合加热至130℃搅拌回流3h,冷却至室温得到无色油状物;
步骤3,步骤2的油状物和NaH在THF中常温搅拌,溶液变成橙色,加入步骤1合成的N,N-二(4-甲酰苯基)苯胺,反应两小时,用冰水淬灭反应,抽滤并柱层析分离,得式I所示的产物。
反应过程如式II所示:
具体地,对氰基溴苄与亚磷酸三乙酯摩尔比为1:1.2;油状物和NaH摩尔比为1:5。
具体地,分离最终产物的展开剂比例为PE:EA=20:1。
第二方面,本发明还提供一种三苯胺染料的应用,将其直接作为荧光指纹粉,应用于潜指纹识别中。
具体地,在潜指纹识别中的应用,具体包括如下步骤:
步骤1,将所制备的三苯胺染料指纹粉用一根洁净的绒毛棒蘸取撒在潜指纹所在的基底材料上,使指纹粉均匀地洒落在基底材料表面,指纹粉会附着在指纹留有处,然后吹落潜指纹所在区域以外的指纹粉;
步骤2,可在日光下观察指纹信息并拓印,在紫外365nm照射下荧光粉显示出黄色荧光。
具体地,所述基底材料为光盘、玻璃、手机屏幕中的至少一种
该三苯胺荧光染料化学分子晶体结构简单,光稳定性良好,光敏感度强,荧光效率高,生物相容性较好且毒性较低。由于其脂溶性良好,可以与指纹中残留的微量的油脂结合,且在紫外365nm照射下显示出黄色荧光,从而更高对比度地展示指纹信息,提高了指纹鉴定效率和结果有效性。
与现有技术相比,本发明的有益效果:
(1)本发明制备的三苯胺荧光染料,其结构以及组成不同于已有的荧光染料,该染料可直接作为指纹粉,不需要与载体相混合,制备所需的原料易得且成本低、制备工艺简单、仅需三步即可得到目标产物,产率较高,且所生产三苯胺荧光染料稳定性好,生物毒性小,同时该荧光染料可与指纹中残留的生物油脂响应展示指纹信息,并在紫外365nm照射下显示出黄色荧光,能够被应用于潜指纹识别中;
(2)本发明制备的三苯胺荧光染料,应用于潜指纹显影中同时具有现有的物理显影法与化学显影法的优点,具有较强的抗干扰性,较高的分辨率和对比度、较高的指纹显现精度,可以实时显示指纹信息且不损伤指纹中的DNA信息;
(3)本发明制备的荧光指纹粉,在潜指纹识别中,不受基底材料的限制,其在光盘、玻璃、手机屏幕等多种生活常见基底上残留指纹的区域均具有优异的潜指纹显影效果,该指纹粉有普遍适用性。
附图说明
为了更清晰地介绍本申请实施例的技术方案,下面将对本申请实施例中所需要使用的附图进行简单地说明,应当理解,以下附图仅示出了本申请的某些实施例,因此不应被看作是对范围的限定,对于本领域普通技术人员来讲,在不付出创造性劳动的前提下,还可以根据这些附图获得其他相关的附图。
图1为实施例1制备的三苯胺荧光染料的核磁共振氢谱图;
图2为实施例1制备的三苯胺荧光指纹粉与手机屏幕上潜指纹响应后在日光照射下的指纹显影成像;
图3为实施例1制备的三苯胺荧光指纹粉与手机屏幕表面上潜指纹响后在紫外灯照射下的指纹显影成像;
图4为实施例1制备的三苯胺荧光指纹粉与手机屏幕表面上潜指纹响后在紫外光照射下的指纹显影成像的细节对比图;
图5为实施例1制备的三苯胺荧光指纹粉与光盘上潜指纹响后在日光照射下的指纹显影成像;
图6为实施例1制备的三苯胺荧光指纹粉与光盘上潜指纹响后在紫外光照射下的指纹显影成像;
图7为实施例1制备的三苯胺荧光指纹粉与玻璃上潜指纹响后在日照射下的指纹显影成像;
图8为实施例1制备的三苯胺荧光指纹粉与玻璃上潜指纹响后在紫外灯照射下的指纹显影成像;
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
制备三苯胺荧光染料:
在50mL双口烧瓶中滴入2.0mL POCl3,待体系温度约为0℃时,将恒压滴液漏斗中的2.0mL DMF逐滴缓慢地滴加到体系中,在0℃下搅拌15min。将3.3961g三苯胺加至体系中。滴加完毕后将混合物加热至130℃,反应期间随时TLC检测反应进度,原料消耗完后冷却至室温。将产物倒入冰水进行搅拌,用饱和碳酸氢钠水溶液将pH值调节到6~7。用乙酸乙酯萃取2次后得到旋干溶剂。最后进行重结晶提纯,用EA将其溶解后升温至70℃直至体系成饱和溶液状态后加入少许PE自然冷却,可看到体系中逐渐有结晶生成,此时进行抽滤,可得到4-甲酰基三苯胺和N,N-二(4-甲酰苯基)苯胺的混合粗纯品,通过柱色谱分离得到N,N-二(4-甲酰苯基)苯胺;
另取50mL单口烧瓶将0.5110g对氰基溴苄和0.5040mL的亚磷酸三乙酯放入其中加热至130℃搅拌回3h,用TLC检测反应。反应完全后冷却至室温,得无色油状物;
将2.6mmol油状物和0.3125g的NaH在20.0mL THF中常温搅拌30min,加入N,N-二(4-甲酰苯基)苯胺,加热30℃反应两小时。用冰水淬灭反应,直接抽滤并干燥,得到的产物可用少量EA加热浆洗或重结晶提纯。最后进行柱层析分离,得产物0.3564g。
三苯胺变色荧光染料的结构如式Ia所示:
核磁检测结果:
图1为实施例1制备的油脂响应变色荧光染料的核磁共振氢谱图。
核磁信息为:1H NMR(500MHz,Chloroform-d)δ7.65(d,J=7.9Hz,4H),7.59(d,J=8.0Hz,4H),7.45(d,J=8.2Hz,4H),7.34(t,J=7.7Hz,2H),7.20(d,J=15.8Hz,5H),7.13(d,J=8.2Hz,5H),7.02(d,J=16.2Hz,2H)。结果显示本实施例制备得到的化合物具有式Ia所示结构。
实施例2
将实施例1制备的三苯胺荧光染料应用于手机屏幕表面的潜指纹显现。
取一根洁净的绒毛棒蘸取适量的指纹粉,在有潜指纹的手机屏幕上方轻轻抖动绒毛棒,使指纹粉均匀地散落在手机屏幕表面,然后吹落指纹所在区域以外的指纹粉并在日光下观察拍照,如图2所示,在UV 365nm下进行观察拍照,如图3所示。
荧光指纹在手机屏幕表面与指纹显影后,用相机拍摄,得到清晰的指纹成像。指纹图像上可得出指纹中包含的多种特征信息如图4,包括2级和3级特征。图4红色标记处为可识别的纹路分叉点(1号位置)、终结点(2号位置)等二级节点以及三级节点汗腺孔(3号位置)等特征。考虑到目前指纹识别的应用场景最高识别等级为三级节点的识别,因此能达到三级识别的指纹粉已经可以满足作为特定场景下实现潜指纹应用的条件,即本小节测试的三苯胺指纹粉可以满足应用于政府、执法等领域的使用需求
实施例3
将实施例1制备的三苯胺荧光染料应用于光盘表面的潜指纹显现。取一根洁净的绒毛棒蘸取适量的指纹粉,在有潜指纹的光盘表面上方轻轻抖动绒毛棒,使指纹粉均匀地散落在光盘表面,然后吹落指纹所在区域以外的指纹粉并在日光下观察拍照,如图5所示,在UV 365nm下进行观察拍照,如图6所示。荧光指纹在光盘表面与指纹显影后,用相机拍摄,得到清晰的指纹成像。
实施例4
将实施例1制备的三苯胺荧光染料应用于玻璃表面的潜指纹显现。取一根洁净的绒毛棒蘸取适量的指纹粉,在有潜指纹的玻璃表面上方轻轻抖动绒毛棒,使指纹粉均匀地散落在玻璃表面,然后用吹尘球吹落指纹所在区域以外的指纹粉并在日光下观察拍照,如图7所示,在UV 365nm下进行观察拍照,如图8所示。荧光指纹在光盘表面与指纹显影后,用相机拍摄,得到清晰的指纹成像
以上所述实施例仅为本发明的优选实施例,对本发明而言,具有说明性的,而并不具有限制;本领域普通技术人员的理解,在本发明专利要求所限定的范围内,可对本发明进行诸多改变甚至等效变更,但都将落入本发明的保护范围。
Claims (6)
1.一种可直接用于潜在指纹显影的三苯胺染料,其特征在于,具有式I的结构:
2.一种权利要求1所述的可直接用于潜在指纹显影的三苯胺染料的制备方法,其特征在于,具体包括以下步骤:
步骤1,0℃下,POCl3和DMF逐滴混合并搅拌15min,三苯胺加至体系中,将混合物加热130℃,反应45min,冷却至室温倒入冰水进行搅拌,用饱和碳酸氢钠水溶液将pH值调节到6~7,用乙酸乙酯萃取后柱色谱分离得到N,N-二(4-甲酰苯基)苯胺;
步骤2,对氰基溴苄和亚磷酸三乙酯混合加热至130℃搅拌回流3h,冷却至室温得到无色油状物;
步骤3,步骤2的油状物和NaH在THF中常温搅拌,溶液变成橙色,加入步骤1合成的N,N-二(4-甲酰苯基)苯胺,反应两小时,用冰水淬灭反应,抽滤并柱层析分离,得式I所示的产物。
3.一种根据权利要求1所述的合成的三苯胺染料的应用,将其作为指纹粉并应用于指纹显影技术。
4.根据权利要求3所述的合成的三苯胺染料的应用,其特征在于,该三苯胺染料不需要与其他化学物质混合,本身即可被直接作为指纹粉并应用于指纹显影。
5.根据权利要求3所述的合成的三苯胺染料的应用,其特征在于,应用于潜在指纹显影中,具体包括如下步骤:
步骤1,将所制备的三苯胺染料撒在潜指纹所在的基底上,使指纹粉均匀地落在基底表面,指纹粉会附着在指纹留有处,然后吹落指纹区域以外的指纹粉粉末,可清晰显示指纹纹路;
步骤2,用紫外365nm照射指纹粉,指纹粉显示出黄色荧光。
6.根据权利要求5所述的制备的三苯胺染料的应用,其特征在于,所述基底为光盘、玻璃、手机屏幕中的至少一种。
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