CN111995579B - 一种含咪唑环结构的四苯乙烯衍生物制备方法和应用 - Google Patents

一种含咪唑环结构的四苯乙烯衍生物制备方法和应用 Download PDF

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CN111995579B
CN111995579B CN202010807678.6A CN202010807678A CN111995579B CN 111995579 B CN111995579 B CN 111995579B CN 202010807678 A CN202010807678 A CN 202010807678A CN 111995579 B CN111995579 B CN 111995579B
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郑开波
陈慧
李梦
王丽红
郑海峡
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China Three Gorges University CTGU
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Abstract

本发明公开了具有AIE性质的荧光染料及其制备方法，提供了结构如式(I)所示的一种四苯乙烯（TPE）衍生物荧光染料的合成方法，其中取代基R为芳基共轭体系，以4‑（1,2,2‑三苯基乙烯基）苯甲醛为起始原料，分别芳基二酮类衍生物反应合成系列含咪唑环的化合物，所述化合物具有典型的聚集诱导发光（AIE）性质；本发明的荧光染料制备方法简单，操作简便，成本低廉，且该系列荧光染料表现出较强的固体荧光。该荧光染料可应用于生物荧光成像等领域。

Description

一种含咪唑环结构的四苯乙烯衍生物制备方法和应用
技术领域
本发明属于精细化工技术领域，具体涉及一类TPE咪唑环类荧光染料的合成和应用，主要包含这一类TPE咪唑环类荧光染料的制备及其在细胞染色中的应用。
背景技术
有机荧光染料分子，作为荧光探针的重要组成部分，被广泛地应用于生物成像、生物分子标记、环境分析、细胞染色和临床检验诊断、光化学治疗、有机发光二极管等方面，是化学、生物学、环境科学、医学和材料研究领域中不可缺少的重要工具。设计合成新型荧光染料、开发具有实用价值的各种功能性荧光染料分子已成为当前倍受关注的研究热点。
目前大部分传统有机染料在稀溶液中发射很强的荧光，有着较好的荧光性质，但这些荧光团在溶液中随着浓度的升高，其发光强度会降低，即由于分子之间的л-л堆积而产生的聚集淬灭现象(Aggregation-caused quenching，ACQ)。因为这类分子只能在良溶剂、低浓度下发光，导致荧光传感系统灵敏度较低，而荧光材料在应用中常以固体和聚集态的形式存在，ACQ效应则大大制约了这类荧光染料的实际应用和发展。2001年，唐本忠院士及其课题组首次发现并提出了聚集诱导发光(Aggregation-induced emission,AIE)这一概念。与大多数ACQ染料相比，AIE荧光染料(AIEgens)在分子溶解时表现出非发射性的荧光，但在聚集态下表现出较强的荧光性,这种具有AIE效应的分子具有良好的发光性能，为设计合成新型荧光染料开辟了新路径。四苯乙烯就是其中典型的AIE分子，其分子中由单键与C＝C双键相连接的苯环可自由旋转，这种非平面的构象可防止π-π堆积，其简单的结构使其成为构建各种荧光传感器、光电材料等的理想模型。除此之外，由于聚集态的强发射，TPE类荧光染料在稀溶液中具有较强的光稳定性和较低的背景噪声，是理想的生物医学应用对象。可作为一种有效的可视化工具，用于特定环境的肿瘤细胞、细胞器成像，长期的细胞追踪，甚至肿瘤的体内成像，还可用于引导药物递送，甚至可以作为癌症光动力的光敏剂治疗。
尽管四苯乙烯结构有着上述优点，但其存在着发射波长短的缺点，容易受到细胞自身荧光的干扰，本发明通过对四苯乙烯结构进行修饰，增大其结构刚性以增大化合物的波长以及改变其荧光量子产率。
发明内容
本发明目的在于提供一种简便高效的AIE荧光染料的合成方法。
本发明目的是提供一种固体荧光染料，该类化合物固体状态下有较强的荧光，具有明显的聚集诱导发光效应。
本发明的目的通过下述技术方案实现：
一种四苯乙烯并咪唑环结构的荧光染料，结构式如下：
Figure BDA0002629748680000021
其中，取代基为芳基共轭体系。
合成所述的四苯乙烯并咪唑环结构荧光染料的方法，所述方法包括以下合成路径：
Figure BDA0002629748680000022
所述的方法，其特征在于，包括以下步骤：
将4-(1,2,2-三苯基乙烯基)苯甲醛和醋酸铵分别与芳基二酮类衍生物溶于乙酸中，在100～120℃下反应2～8h，反应结束后，将反应物逐渐倒入冰水中，有沉淀析出，经过滤、洗涤、干燥后得到目标化合物粗产品。
所述的芳基二酮类衍生物包括1，10-菲罗啉-5，6-二酮、9，10-菲醌、苯偶酰、间二硝基苯偶酰、2,2'-吡啶酮等中的任意一种。
所述的4-(1,2,2-三苯基乙烯基)苯甲醛和醋酸铵分别与芳基二酮类衍生物的摩尔比为1：(2～6)：(0.5～2)。
作为优选方案的荧光染料，其合成路线如下：
Figure BDA0002629748680000031
本发明所述四苯乙烯并咪唑环结构的荧光染料合成方法简便，一步反应即可完成，反应条件比较温和，产品较易制备，后处理简单。本发明合成的四苯乙烯并咪唑环结构的荧光染料1-4在固体状态下均有荧光，具有典型的聚集诱导发光(AIE)效应，即该化合物在四氢呋喃-水的混合溶液时，当有机溶剂THF的含量比较高时，化合物可以较好的溶解在THF中，化合物分子在溶液中可以通过单双键的自由旋转和振动等以非辐射衰减的方式释放激发态的能量，而辐射衰减渠道为打开，从而化合物此时在溶液中基本不发光。而当含水量的增加，化合物溶解度降低，形成聚集态，分子内的自由旋转和振动受到了很大的阻碍，激发态分子的能量就会以辐射光子的方式释放，此时就会显现出很强的荧光。可应用于生物成像等领域。化合物5由于有两个硝基基团，强的吸电子作用使得分子荧光淬灭。
附图说明
图1为实施例1中化合物1的核磁共振氢谱图。
图2为实施例2中化合物2的核磁共振氢谱图。
图3为实施例3中化合物3的核磁共振氢谱图。
图4为实施例4中化合物4的核磁共振氢谱图。
图5为本发明化合物1在不同比例四氢呋喃(THF)/水的混合溶剂中的荧光光谱。
图6为本发明化合物2在不同比例四氢呋喃(THF)/水的混合溶剂中的荧光光谱。
图7为本发明化合物3在不同比例四氢呋喃(THF)/水的混合溶剂中的荧光光谱。
图8为本发明化合物4在不同比例四氢呋喃(THF)/水的混合溶剂中的荧光光谱。
图9为本发明化合物5在不同比例四氢呋喃(THF)/水的混合溶剂中的荧光光谱。
图10为本发明化合物1的细胞成像图。图A为染料溶液处理的细胞明场成像，图B为染料溶液处理的细胞中蓝光通道成像，图C为细胞明场和蓝光通道成像的叠加。
图11为本发明化合物2的细胞成像图。图A为染料溶液处理的细胞明场成像，图B为染料溶液处理的细胞中蓝光通道成像，图C为细胞明场和蓝光通道成像的叠加。
图12为本发明化合物3的细胞成像图。图A为染料溶液处理的细胞明场成像，图B为染料溶液处理的细胞中蓝光通道成像，图C为细胞明场和蓝光通道成像的叠加。
图13为本发明化合物4的细胞成像图。图A为染料溶液处理的细胞明场成像，图B为染料溶液处理的细胞中蓝光通道成像，图C为细胞明场和蓝光通道成像的叠加。
具体实施方式
染料的合成
下面结合实施例来进一步说明本发明，但本发明要求保护的范围并不局限于实施例表述的范围。
实施例1：化合物1的合成
称取4-(1,2,2-三苯基乙烯基)苯甲醛(53.8mg,0.15mmol)、醋酸铵(57.9mg,0.75mmol)和1，10-菲罗啉-5，6-二酮(37.9mg,0.18mmol)溶于5ml乙酸中，在110℃下回流反应3.5h。反应结束后，将反应液倒入20mL的水，有橘黄色固体析出，过滤后水洗、干燥后得到橘黄色固体，即为染料1，收率58.9％。
实施例2：化合物2的合成
称取4-(1,2,2-三苯基乙烯基)苯甲醛(54.1mg,0.15mmol)、醋酸铵(57.8mg,0.75mmol)和9，10-菲醌(37.5mg,0.18mmol)溶于5ml乙酸中，在110℃下回流反应3.5h。反应结束后，将反应液倒入20mL的水，有橘黄色固体析出，过滤后水洗、干燥后得到淡黄色固体，即为染料2，收率78.4％。
实施例3：化合物3的合成
称取4-(1,2,2-三苯基乙烯基)苯甲醛(72mg,0.2mmol)、醋酸铵(77mg,1mmol)和苯偶酰(63mg,0.3mmol)溶于5ml乙酸中，在110℃下回流反应3.5h。反应结束后，将反应液倒入20mL的水，有黄色固体析出，过滤后水洗、干燥后得到白色固体，即为染料3，收率50.5％。
实施例4：化合物4的合成
称取4-(1,2,2-三苯基乙烯基)苯甲醛(54.1mg,0.15mmol)、醋酸铵(58.2mg,0.76mmol)和2,2'-吡啶酮(48.2mg,0.227mmol)溶于5ml乙酸中，在110℃下回流反应3.5h。反应结束后，用氢氧化钠溶液中和，然后用二氯甲烷进行萃取，有机层经无水硫酸钠干燥后过柱，过柱极性为乙酸乙酯：石油醚＝1：8，得到黄色固体，即为染料4，收率22.2％。
实施例5：化合物5的合成
称取4-(1,2,2-三苯基乙烯基)苯甲醛(72mg,0.2mmol)、醋酸铵(78.1mg,1mmol)和间二硝基苯偶酰(90.1mg,0.3mmol)溶于5ml乙酸中，在110℃下回流反应4h。反应结束后，将反应液倒入20mL的水，有黄色固体析出，过滤后水洗、干燥后得到黄色固体，即为化合物5，收率81.54％。
实施例6
采用荧光光谱仪测试实施例1-5制备得到的化合物1、2、3、4和5在不同比例的水和四氢呋喃(THF)的混合溶液中的荧光强度，测试结果见图5-9。从图5-8中可知，化合物1、2、3和4在水含量为0％-70％时，荧光强度维持在一个较低的值；随着水含量达到70％和80％时，分子发生聚集，荧光强度有一个明显的增加，在95％时，荧光强度达到最大，以上结果说明本发明制备得到的荧光化合物具有明显的聚集诱导发光性能。化合物5没有明显荧光(图9)。
实施例7：
将染料溶于DMF中，配制成500μM的溶液，用5μM的染料在37℃下培养细胞20min，通过激光共聚焦扫描显微镜，以405nm作为激发波长，观察到在细胞中有较强的信号，说明该探针可用于细胞成像，光学性质数据如图10-13所示。此外，从细胞的形态看，使用该染料培养细胞20min后仍为活细胞，说明该染料对细胞毒性较低。

Claims (4)

1.一种四苯乙烯并咪唑环结构的荧光染料，其特征在于，结构式如下：
Figure FDA0003246325670000011
2.根据权利要求1所述的四苯乙烯并咪唑环结构的荧光染料的制备方法，其特征在于，所述方法包括以下步骤：
将4-(1,2,2-三苯基乙烯基)苯甲醛和醋酸铵分别与芳基二酮类衍生物溶于乙酸中，芳基二酮类衍生物为1,10-菲罗啉-5,6-二酮或2,2'-吡啶酮，在110℃下反应2～10h，反应结束后，将反应物逐渐倒入冰水中，有沉淀析出，经过滤、洗涤、干燥后得到目标化合物粗产品。
3.根据权利要求2所述的制备方法，其特征在于，所述的4-(1,2,2-三苯基乙烯基)苯甲醛、醋酸铵与芳基二酮类衍生物的摩尔比为1：(2～6)：(0.5～2)。
4.根据权利要求1所述的四苯乙烯并咪唑环结构的荧光染料在制备生物荧光成像剂中的应用。
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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103965865A (zh) * 2014-05-05 2014-08-06 吉林大学 一种压致变色材料其制备方法及应用
CN109134382A (zh) * 2018-08-20 2019-01-04 浙江工业大学 具有esipt与aie性质的菲并咪唑衍生物及其制备方法与应用
CN109627217A (zh) * 2019-01-23 2019-04-16 广东工业大学 一种四苯乙烯-菲并咪唑衍生物及其晶体、制备方法与应用
CN110256218A (zh) * 2019-06-17 2019-09-20 三峡大学 一种聚集诱导发光染料分子及其合成方法

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103965865A (zh) * 2014-05-05 2014-08-06 吉林大学 一种压致变色材料其制备方法及应用
CN109134382A (zh) * 2018-08-20 2019-01-04 浙江工业大学 具有esipt与aie性质的菲并咪唑衍生物及其制备方法与应用
CN109627217A (zh) * 2019-01-23 2019-04-16 广东工业大学 一种四苯乙烯-菲并咪唑衍生物及其晶体、制备方法与应用
CN110256218A (zh) * 2019-06-17 2019-09-20 三峡大学 一种聚集诱导发光染料分子及其合成方法

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
A series of tetraphenylethene-based benzimidazoles: syntheses, structures, aggregation-induced emission and reversible mechanochromism;Tengfei Zhang et al.;《RSC Advances》;20160817;第6卷(第83期);第79871-79878页 *
Amjad Islam et al..Non-Doped Sky-Blue OLEDs Based on Simple Structured AIE Emitters with High Efficiencies at Low Driven Voltages.《Chemistry-An Asian Journal》.2017,第12卷(第17期),第2189-2196页. *
Non-Doped Sky-Blue OLEDs Based on Simple Structured AIE Emitters with High Efficiencies at Low Driven Voltages;Amjad Islam et al.;《Chemistry-An Asian Journal》;20170804;第12卷(第17期);第2189-2196页 *
Synthesis and characterization of blue light emitting materials containing imidazole;Zhangjian Fang et al.;《Materials Chemistry and Physics》;20070904;第107卷(第2-3期);第305-309页 *
Tengfei Zhang et al..A series of tetraphenylethene-based benzimidazoles: syntheses, structures, aggregation-induced emission and reversible mechanochromism.《RSC Advances》.2016,第6卷(第83期),第79871-79878页. *

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