CN116947737A - 一种四苯乙烯-查尔酮衍生物的制备及其应用 - Google Patents

一种四苯乙烯-查尔酮衍生物的制备及其应用 Download PDF

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CN116947737A
CN116947737A CN202310690549.7A CN202310690549A CN116947737A CN 116947737 A CN116947737 A CN 116947737A CN 202310690549 A CN202310690549 A CN 202310690549A CN 116947737 A CN116947737 A CN 116947737A
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tetraphenyl ethylene
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chalcone derivative
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郑开波
杨嘉琇
余威
肖宇峰
张诺诺
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China Three Gorges University CTGU
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Abstract

本发明公开了一种四苯乙烯‑查尔酮衍生物的制备及其应用的制备及其应用。其结构如下：所述方法包括：将4‑(1,2,2‑三苯基乙烯基)苯乙酮、醛衍生物、氢氧化钠(提供碱性条件，pH＝8.3～8.5)、置于无水乙醇中，在加热温度为80℃条件下，回流反应12h，反应结束后分离纯化得到所述功能有机材料。按照上述方法合成的功能有机材料具有较大的共轭体系，且具有显著压力致变色特性。本发明所述的功能有机材料制备成本低廉，操作简便，方法简单，且该材料表现出显著压力致变色特性，可应用于压致变色、发光材料、印染、彩色印刷和防伪技术领域。

Description

一种四苯乙烯-查尔酮衍生物的制备及其应用
技术领域
本发明属于有机合成领域，具体涉及一种四苯乙烯-查尔酮衍生物的制备方法。
背景技术
查尔酮衍生物是有机合成中一种重要的活性中间体。它是一种存在于甘草、红花等药用植物中的天然化合物，是植物体内合成黄酮的前体，是一种天然无毒副作用的药物。查尔酮类化合物及其衍生物包含有许多反应活性中心，在多数重要的化学反应中都有较为广泛的应用。查尔酮及衍生物还具有广泛的药理学作用，可发挥抗病毒、抗菌抗炎、抗氧化、抗纤维等多种作用。
四苯乙烯(TPE)是典型的AIE有机荧光染料，其结构中有可绕碳碳双键自由旋转的苯环，聚集态时阻止了π-π堆积，限制了分子内的旋转和振动因而其具有较好的固态发光性能。通过对TPE进行结构修饰，也能改变其荧光性质，如使其在溶剂中具有良好的荧光发射、波长红移等。
查尔酮由于其结构能够发生分子内电荷转移(ICT)过程其由供体-受体(D-π-A)框架组成的推拉式结构已被广泛应用于荧光材料中，通过在TPE单元上引入查尔酮结构，构建了基于D-A-D框架的TPE功能有机材料。这些D-π-A框架的衍生物由TPE基团、不同的取代芳环和查尔酮结构三部分组成。基于化合物的ICT过程和不同的π-π堆积模式，这些功能有机材料表现出独特的荧光性质。
本发明将二者(四苯乙烯和查尔酮)结合起来，对查尔酮骨架进行修饰，发明了一种新的方法来合成四苯乙烯-查尔酮衍生物，即采用高度共轭结构的反应物4-(1,2,2-三苯基乙烯基)苯乙酮与各类芳香醛衍生物，以及氢氧化钠(提供碱性条件，pH＝8.3～8.5)以无水乙醇溶剂(效果最佳)，条件温和，此种方法与之前合成查尔酮衍生物相比，原料易得、价格便宜、操作简单等。
发明内容
本发明目的是提供一种一种四苯乙烯-查尔酮衍生物的制备及应用，该化合物显著的压力致变色特性。
本发明的目的通过下述技术方案实现：
四苯乙烯-查尔酮衍生物的压力致变色功能有机材料，该材料分子的结构式如下：
所述的压力致变色功能有机材料的制备方法包括以下步骤：将4-(1,2,2-三苯基乙烯基)苯乙酮、芳香醛衍生物、氢氧化钠(提供碱性条件，pH＝8.3～8.5)置于无水乙醇中进行加热回流反应，反应结束后分离纯化得到所述功能有机材料，
具体的合成过程如下所示：
所述的芳香醛衍生物的结构包括下式中的任意一种：
所述的4-(1,2,2-三苯基乙烯基)苯乙酮、芳香醛衍生物的摩尔比为1：1-1.1。
所述回流反应温度为在70-90℃下反应10-12h。
所述反应溶剂为无水乙醇。本申请的技术方案也尝试过无水甲醇，但是反应进行效果很差，
4-(1,2,2-三苯基乙烯基)苯乙酮在甲醇中基本不溶解，点板监测，没有目标产物生成，采用二氯甲烷时也并未产生目标产物。
本文的创新点在于用共轭性较强4-(1,2,2-三苯基乙烯基)苯乙酮以及各类芳香醛做底物，以氢氧化钠(提供碱性条件，pH＝8.3～8.5)，以无水乙醇为溶剂，原料易得，反应条件温和，操作简便，易于提纯。
本发明合成的功能有机材料具有较大的共轭体系，且材料分子均具有显著的压力致变色性，本发明所述的制备方法简单，操作简便，成本低廉，可应用于发光材料、压致变色材料印染、彩色印刷(荧光油墨)和防伪领域。
附图说明
图1为B-1的核磁共振氢谱图。
图2为B-1的核磁共振碳谱图。
图3为B-2的核磁共振氢谱图。
图4为B-2的核磁共振碳谱图。
图5为B-3的核磁共振氢谱图。
图6为B-3的核磁共振碳谱图。
图7为B-1研磨前后的荧光光谱图。
图8为B-1研磨前后的颜色变化。
图9为B-1研磨前后的粉末XRD图。
图10为功能有机材料分子B-1的应用。
图11为B-3研磨前后的荧光光谱图。
图12为B-3研磨前后的颜色变化。
图13为B-3研磨前后的粉末XRD图。
图14为功能有机材料分子B-3的应用。
具体实施方式
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：B-1材料分子的合成
4-(1,2,2-三苯基乙烯基)苯乙酮(149.8mg，0.4mmol)、4-(10H-吩噻嗪-10-基)苯甲醛(108.5mg，0.4mmol)、氢氧化钠(68.8mg，1.72mmol)、6mL无水乙醇按顺序加入至25mL的反应瓶中，在加热温度80℃条件下反应12h后，旋干乙醇，经柱层析(PE:EA＝25：1)得到所述的黄橙色材料分子，质量85.6mg，产率32.5％。
结构式如下：
实施例2：B-2材料分子的合成
4-(1,2,2-三苯基乙烯基)苯乙酮(149.8mg，0.4mmol)、4-(9H-咔唑-9-基)苯甲醛(121.2mg，0.4mmol)、氢氧化钠(68.8mg，1.72mmol)、6mL无水乙醇按顺序加入至25mL的反应瓶中，在加热温度80℃条件下反应12h后，旋干乙醇，经柱层析(PE:EA＝20：1)得到所述的黄绿色材料分子，质量为92.3mg，产率36.8％。
结构式如下：
实施例3：B-3材料分子的合成
4-(1,2,2-三苯基乙烯基)苯乙酮(149.8mg，0.4mmol)、4-(9,9-二甲基-10(9H)-吖啶)苯甲醛(125.2mg，0.4mmol)、氢氧化钠(68.8mg，1.72mmol)、6mL无水乙醇按顺序加入至25mL的反应瓶中，在加热温度80℃条件下反应12h后，旋干乙醇，经柱层析(PE:EA＝25：1)得到所述的黄色材料分子，质量为94.6mg，产率35.3％。
结构式如下：
实施例4：B-4材料分子的合成
4-(1,2,2-三苯基乙烯基)苯乙酮(149.8mg，0.4mmol)、4-(10H-吩吩噁嗪-10-基)苯甲醛(114.8mg，0.4mmol)、氢氧化钠(68.8mg，1.72mmol)、6mL无水乙醇按顺序加入至25mL的反应瓶中，在加热温度80℃条件下反应12h后，旋干乙醇，经柱层析(PE:EA＝25：1)得到所述的黄橙色材料分子，质量为82.3mg，产率31.4％。
结构式如下：
实施例5：B-5材料分子的合成
4-(1,2,2-三苯基乙烯基)苯乙酮(149.8mg，0.4mmol)、9-蒽甲醛(82.4mg，0.4mmol)、氢氧化钠(68.8mg，1.72mmol)、6mL无水乙醇按顺序加入至25mL的反应瓶中，在加热温度80℃条件下反应12h后，旋干乙醇，经柱层析(PE:EA＝25：1)得到所述的橙色材料分子，质量为118.9mg，产率52.9％。
实施例6
将实施例1中制备好的黄橙色材料分子B-1，称取5mg放入研钵里，用研杵研磨1min后，用365紫外灯照射发现，染料分子由之前的黄橙色变为橙色，将研磨后的橙色染料用正己烷搅拌洗涤2min可得到黄橙色分子。得到的黄橙色分子又可以研磨至橙色，橙色染料亦可以洗涤至黄橙色，此过程可实现无限次的循环。
图7和图8分别为黄橙色材料分子B-1研磨前后的荧光光谱图及颜色变化图，图7中pristine表示原始固体粉末(未研磨之前的固体)，ground表示研磨之后的固体粉末，soaked表示研磨后用正己烷洗涤的固体粉末；由图8可以看出，染料分子通过研磨后最大发射波长红移34nm，并且荧光颜色从黄橙色变为橙色，用正己烷洗涤研磨的固体粉末后又能恢复黄橙色，说明染料分子具有良好的压力致变色性质且具有良好的可逆性。
图9为B-1研磨前后的粉末XRD图，图9中pristine表示原始固体粉末及未研磨之前的固体(上)，ground表示研磨之后的固体粉末(中)，soaked表示研磨后用石油醚洗涤固体粉末(下)；根据图9可以看出，染料分子研磨前显示出清晰且尖锐的衍射峰，表明有序的晶体性质，而研磨后固体显示出相当弱的衍射，表明研磨样品为非晶态性质，力破坏或削弱了分子间的相互作用，这种晶态到非晶态的转变导致了荧光颜色的红移。然而，正己烷洗涤大大提高了结晶度，同时出现了尖锐的衍射峰，并且与原始衍射峰吻合良好，荧光颜色也恢复到了研磨前的黄橙色。
图10为功能有机材料分子B-1的应用，具体实施过程：将黄橙色的染料分子平整地铺在之上，然后再纸上写出一个“A”字，然后在365nm荧光灯下，会发现这个“A”是橙色的，可见该种染料分子能够很好地用作读写的器件，具有潜在防伪应用。
材料分子B-3也可用同上方法研磨，具体的颜色变化可见图11。图11和图12分别为B-3研磨前后的荧光光谱图及颜色变化图，图11中pristine表示原始固体粉末(未研磨之前的固体)，ground表示研磨之后的固体粉末，soaked表示研磨后用正己烷洗涤的固体粉末；由图可以看出，B-3通过研磨后最大发射波长红移18nm，并且荧光颜色从黄绿色变为黄色，用正己烷洗涤研磨的固体粉末后又能恢复黄绿色，说明染料分子具有良好的压力致变色性质且具有良好的可逆性。
图13为B-3研磨前后的粉末XRD图，图13中pristine表示原始固体粉末及未研磨之前的固体(上)，ground表示研磨之后的固体粉末(中)，soaked表示研磨后用石油醚洗涤固体粉末(下)；根据图13可以看出，染料分子研磨前显示出清晰且尖锐的衍射峰，表明有序的晶体性质，而研磨后固体显示出相当弱的衍射，表明研磨样品为非晶态性质，力破坏或削弱了分子间的相互作用，这种晶态到非晶态的转变导致了荧光颜色的红移。然而，正己烷洗涤大大提高了结晶度，同时出现了尖锐的衍射峰，并且与原始衍射峰吻合良好，荧光颜色也恢复到了研磨前的黄绿色。
图14为能有机材料分子B-3的应用，具体实施过程：将黄绿色的染料分子平整地铺在之上，然后再纸上写出一个“F”字，然后在365nm荧光灯下，发现这个“F”是深黄色的，可见该种染料分子能够很好地用作读写的器件，具有潜在防伪应用。
以上结合实施例对本发明的实施方式，作了详细说明，但本发明不限于所描述的实施方式。对于本领域的技术人员而言，在不脱离本发明原理和精神的情况下，对这些实施方式进行多种变化、修改、替换和变型，仍落入本发明的保护范围内。

Claims (6)

1.一种四苯乙烯-查尔酮衍生物，其特征在于，该化合物的结构式包括下述结构式中的任意一种：
2.根据权利要求1所述的四苯乙烯-查尔酮衍生物的制备方法，其特征在于，包括以下步骤：将4-(1,2,2-三苯基乙烯基)苯乙酮、芳香醛衍生物、氢氧化钠(提供碱性条件，pH＝8.3～8.5)置于溶剂中进行加热回流反应，反应结束后分离纯化得到所述功能有机材料，
具体的合成过程如下所示：
3.根据权利要求2所述的四苯乙烯-查尔酮衍生物的制备方法，其特征在于，所述的芳香醛衍生物的结构包括下式中的任意一种：
4.根据权利要求2所述的四苯乙烯-查尔酮衍生物的制备方法，其特征在于，所述的4-(1,2,三苯基乙烯基)苯乙酮、芳香醛衍生物的摩尔比为1：1-1.1。
5.根据权利要求2所述的四苯乙烯-查尔酮衍生物的制备方法，其特征在于，所述回流反应温度为在70-90℃下反应10-12h。
6.根据权利要求2所述的四苯乙烯-查尔酮衍生物的制备方法，其特征在于，所述反应溶剂为无水乙醇。
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CN117682979A (zh) * 2024-02-04 2024-03-12 有研工程技术研究院有限公司 一种酸致变色化合物及其制备方法和应用

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN117682979A (zh) * 2024-02-04 2024-03-12 有研工程技术研究院有限公司 一种酸致变色化合物及其制备方法和应用
CN117682979B (zh) * 2024-02-04 2024-05-31 有研工程技术研究院有限公司 一种酸致变色化合物及其制备方法和应用

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