CN110305114B - 一种具有聚集诱导荧光和压致荧光变色性质的蒽基荧光材料及其应用 - Google Patents

一种具有聚集诱导荧光和压致荧光变色性质的蒽基荧光材料及其应用 Download PDF

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CN110305114B
CN110305114B CN201810259477.XA CN201810259477A CN110305114B CN 110305114 B CN110305114 B CN 110305114B CN 201810259477 A CN201810259477 A CN 201810259477A CN 110305114 B CN110305114 B CN 110305114B
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induced fluorescence
anthracene
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王磊
刘威
穆广园
庄少卿
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Wuhan Shangsai Optoelectronics Technology Co ltd
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Abstract

本发明公开了一类具有聚集诱导荧光和压致荧光变色性质的蒽基荧光材料。该类材料可通过简单的耦合反应制得，其在有机溶剂中具有较好的溶解性，而在水中几乎不溶解，在水和有机溶剂中可以形成纳米聚集态，具有良好的聚集诱导荧光特性。同时通过研磨该类材料的固态粉末，该类材料的荧光发射波长会向长波方向移动，用二氯甲烷熏蒸后荧光发射波长则会恢复，再研磨时该类材料的荧光发射波长依然会向长波方向移动，采用加热的方法该类材料的荧光发射波长则会恢复，具有可回复的压致荧光变色性能。具有压致荧光变色性质的荧光材料是一种新型的智能材料，它在复写纸、密写纸和机械力传感方面有着非常重要的应用。

Description

一种具有聚集诱导荧光和压致荧光变色性质的蒽基荧光材料 及其应用
技术领域
本发明属于荧光材料技术领域，特别涉及一种具有聚集诱导荧光和压致荧光变色性质的蒽基荧光材料及其应用。
背景技术
荧光材料由于其在光电器件、环境传感器、生物科学等领域具有重大的应用价值，近年来引起了科学家们的极大关注。传统的荧光材料在溶液态时发光较强，在聚集态下会发生聚集淬灭即ACQ，这大大限制了这类材料的实际应用。2001年，唐本忠课题组设计合成一种新型的硅杂环戊二烯类化合物，他们发现该化合物在溶液中时几乎不发光，而在聚集态下化合物发光较强，他们将这种现象命名为聚集诱导荧光(AIE)，AIE的发现为共轭有机发光材料的实际应用拓宽了道路，随后他们对AIE的机理进行了深入的研究，目前普遍认为具有AIE效应的分子在溶液态时处于单分子状态，由于分子内某两种基团的相互作用导致了分子扭曲，这种扭曲作用在光激发的作用下会产生剧烈的扭摆运动，会耗散大量的能量，因而发出的荧光减弱。而在聚集态或固态下，由于分子的适当堆积，这种扭摆运动就受到了限制，受光激发时，主要能量都用于发光，因此表现出很强的荧光特性。
随着对AIE材料的不断研究，具有AIE性质的材料在荧光传感、有机电致发光二极管和压致荧光变色等方面的实际应用也得到了很大程度的发展。由于大多数具有AIE性质的化合物具有扭曲的分子构象，导致分子堆积相对松散，在受到外界刺激时由于堆积方式的改变会呈现不同的发光行为，即压致荧光变色性质。压致荧光变色(piezofluoro-chromism,PFC)是指化合物在机械力作用下，如研磨、剪切、压力等，其荧光光色发生明显变化的一种现象。具有压致荧光变色性质的荧光材料是一种新型的智能材料，它在复写纸、密写纸和机械力传感方面有着非常重要的应用。但是目前为止已经报道的具有压致荧光变色的荧光材料还不是很多，所以设计合成新型的具有压致变色性质的聚集诱导发光材料仍然被迫切需要。
发明内容
为解决以上技术问题，本发明提供了一种具有聚集诱导荧光和压致荧光变色性质的蒽基荧光材料，其特征在于，其结构通式如下列结构式：
Figure BDA0001609882580000021
其中，D为给电子基团；A为吸电子基团。
优选的，所述D是下列取代或未取代的基团2a～2h中的任意一种：
Figure BDA0001609882580000022
其中，*为与蒽连接的位点。
优选的，所述A是下列取代或未取代的基团3a～3f中的任意一种：
Figure BDA0001609882580000031
其中，*为与蒽连接的位点。
优选的，所述蒽基荧光材料为下列化合物中的任一种：
Figure BDA0001609882580000032
Figure BDA0001609882580000041
Figure BDA0001609882580000051
以上所示化合物1-48是符合本发明精神和原则的代表结构，应当理解，列出以上化合物的具体结构，只是为了更好地解释本发明，并非是对本发明的限制。
本发明还提供了一种上述具有聚集诱导荧光和压致荧光变色性质的蒽基荧光材料的制备方法，包括以下路线：
第一步：
Figure BDA0001609882580000061
第二步：
Figure BDA0001609882580000062
其中，D为给电子基团；A为吸电子基团。
具体的，所述第一步中，9-溴蒽和A-B(OH)2按照摩尔比例0.8～0.85比例投料，Suzuki反应的具体反应条件为：辅助原料包括四-三苯基磷钯、碳酸钾、乙醇和甲苯，所述四-三苯基磷钯与所述9-蒽硼酸的摩尔比例为1:169～1:170,当所述碳酸钾的浓度2Mol/L时，所述碳酸钾、乙醇和甲苯的体积比为1:1:2；
则所述第二步中，A取代蒽基和NBS(氮溴代丁二酰亚胺)按照摩尔比例0.8～0.85投料，A取代溴化蒽与D-B(OH)2按照摩尔比例0.8～0.85投料，Suzuki反应的具体反应条件为：辅助原料包括四-三苯基磷钯、碳酸钾、乙醇和甲苯，所述四-三苯基磷钯与所述D-B(OH)2的摩尔比例为0.01～0.02,当所述碳酸钾的浓度2Mol/L时，所述碳酸钾、乙醇和甲苯的体积比为1:1:2；
或者，
所述第一步中，9-蒽硼酸和A-Br按照摩尔比例0.9～0.95比例投料，Suzuki反应的具体反应条件为：辅助原料包括四-三苯基磷钯、碳酸钾、乙醇和甲苯，所述四-三苯基磷钯与所述9-溴蒽的摩尔比例为1:195～1:196,当所述碳酸钾的浓度2Mol/L时，所述碳酸钾、乙醇和甲苯的体积比为1:1:2；
则所述第二步中，A取代蒽基和NBS(氮溴代丁二酰亚胺)按照摩尔比例0.8～0.85投料，A取代溴化蒽与D-B(OH)2按照摩尔比例0.9～1.0投料，Suzuki反应的具体反应条件为：辅助原料包括四-三苯基磷钯、碳酸钾、乙醇和甲苯，所述四-三苯基磷钯与所述D-B(OH)2的摩尔比例为0.02～0.03,当所述碳酸钾的浓度2Mol/L时，所述碳酸钾、乙醇和甲苯的体积比为1:1:2。
本发明还提供了一种上述具有聚集诱导荧光和压致荧光变色性质的蒽基荧光材料的应用，所述蒽基荧光材料用于制作传感器和/或光电功能器件。
本发明的具有聚集诱导荧光和压致荧光变色性质的蒽基荧光材料可以通过简单的耦合反应制得。本发明的荧光材料在普通的有机溶剂中都具有很好的溶解性，而在水中几乎不溶解，在水和有机溶剂中可以形成纳米聚集态，具有良好的聚集诱导荧光特性。同时通过研磨该类材料的固态粉末该类材料的荧光发射波长会向长波方向移动，用二氯甲烷熏蒸后荧光发射波长则会恢复，再研磨时该类材料的荧光发射波长依然会向长波方向移动，采用加热的方法该类材料的荧光发射波长则会恢复，具有可回复的压致荧光变色性能。具有压致荧光变色性质的荧光材料是一种新型的智能材料，它在复写纸、密写纸和机械力传感方面有着非常重要的应用。
附图说明
图1为本发明化合物1在不同四氢呋喃和水的比例中表现出的聚集诱导荧光性质；
图2为本发明化合物1在压力、热恢复和溶剂熏蒸下表现出的压致荧光变色性质；
图3为本发明化合物7在不同四氢呋喃和水的比例中表现出的聚集诱导荧光性质；
图4为本发明化合物7在压力、热恢复和溶剂熏蒸下表现出的压致荧光变色性质；
图5为本发明化合物13在不同四氢呋喃和水的比例中表现出的聚集诱导荧光性质；
图6为本发明化合物13在压力、热恢复和溶剂熏蒸下表现出的压致荧光变色性质。
具体实施方式
下面结合实施例对本发明做进一步说明。依据本发明的技术实质对以下实施例所作的任何简单修改、等同变化等，仍属于本发明技术方案的保护范围。本发明不限于以下实施例中所述的内容。
实施例1
反应路线如下：
Figure BDA0001609882580000081
2-(9-蒽基)-4,6-二苯基-1,3,5-三嗪的合成：
将10.00g 9-蒽硼酸(45.03mmol)和13.26g 2-氯-4,6-二苯基-1,3,5-三嗪(49.54mmol)加入到干净的三口烧瓶中，抽换氮气三次，然后将0.26g四-三苯基磷钯(0.23mmol)加入到烧瓶中，抽换氮气三次，随后将60毫升2M的碳酸钾溶液、60毫升的乙醇和120毫升的甲苯加入到烧瓶中，抽换氮气三次，然后110摄氏度下搅拌反应12小时，停止反应，将温度降至室温，然后用旋转蒸发仪蒸出乙醇和甲苯，残渣用水和二氯甲烷萃取三次，有机相用无水硫酸镁干燥，过滤，然后蒸出二氯甲烷，粗产物用甲苯重结晶得到产物17.55g。(产率：95.17％)
2-(9-溴化蒽基)-4,6-二苯基-1,3,5-三嗪的合成：
将15.00g 2-(9-蒽基)-4,6-二苯基-1,3,5-三嗪(36.66mmol)、7.82g氮溴代丁二酰亚胺(43.96mmol)和400毫升三氯甲烷加入到干净的烧瓶中，抽换氮气三次，然后60摄氏度下搅拌反应1小时，停止反应，将温度降至室温，然后用旋转蒸发仪蒸出三氯甲烷，残渣用丙酮溶解，然后加入甲醇析出固体，过滤得到产物16.68g。(产率：93.18％)
化合物1的合成：
将1.29g 4-硼酸-9-苯基咔唑(4.50mmol)和2.00g 2-(9-溴化蒽基)-4,6-二苯基-1,3,5-三嗪(4.10mmol)加入到干净的三口烧瓶中，抽换氮气三次，然后将0.14g四-三苯基磷钯(0.12mmol)加入到烧瓶中，抽换氮气三次，随后将30毫升2M的碳酸钾溶液、30毫升的乙醇和60毫升的甲苯加入到烧瓶中，抽换氮气三次，然后110摄氏度下搅拌反应12小时，停止反应，将温度降至室温，然后用旋转蒸发仪蒸出乙醇和甲苯，残渣用水和二氯甲烷萃取三次，有机相用无水硫酸镁干燥，过滤，然后蒸出二氯甲烷，粗产物用甲苯重结晶得到产物2.40g。(产率：90.05％)
将化合物1加入含有不同比例的四氢呋喃和水的溶剂中，研究其聚集诱导效应。图1所示，化合物1在不同四氢呋喃和水的比例中表现出的聚集诱导荧光性质，从图中可以看出随着不良溶剂水的加入，其荧光强度逐渐增强，表明该化合物1具有明显的聚集诱导荧光性质。
连续对化合物1进行研磨、热恢复和溶剂熏蒸等操作，研究其压致荧光变色性质。图2所示，本实施例化合物1在压力、热恢复和溶剂熏蒸下表现出的压致荧光变色性质，从图中可以看出当对化合物进行研磨时其荧光光色发生明显的红移，而研磨后进行溶剂熏蒸化合物的光色回复原来的荧光光色，再对化合物进行研磨其荧光光色再次发生红移，再研磨的样品进行加热后化合物的光色回复到原来的荧光光色，表明该化合物具有可回复的压致荧光变色性质。
实施例2
反应路线如下：
Figure BDA0001609882580000101
2-(9-蒽基)-4,6-二苯基-1,3,5-三嗪的合成：
将10.00g 9-蒽硼酸(45.03mmol)和13.26g 2-氯-4,6-二苯基-1,3,5-三嗪(49.54mmol)加入到干净的三口烧瓶中，抽换氮气三次，然后将0.26g四-三苯基磷钯(0.23mmol)加入到烧瓶中，抽换氮气三次，随后将60毫升2M的碳酸钾溶液、60毫升的乙醇和120毫升的甲苯加入到烧瓶中，抽换氮气三次，然后110摄氏度下搅拌反应12小时，停止反应，将温度降至室温，然后用旋转蒸发仪蒸出乙醇和甲苯，残渣用水和二氯甲烷萃取三次，有机相用无水硫酸镁干燥，过滤，然后蒸出二氯甲烷，粗产物用甲苯重结晶得到产物17.55g。(产率：95.17％)
2-(9-溴化蒽基)-4,6-二苯基-1,3,5-三嗪的合成：
将15.00g 2-(9-蒽基)-4,6-二苯基-1,3,5-三嗪(36.66mmol)、7.82g氮溴代丁二酰亚胺(43.96mmol)和400毫升三氯甲烷加入到干净的烧瓶中，抽换氮气三次，然后60摄氏度下搅拌反应1小时，停止反应，将温度降至室温，然后用旋转蒸发仪蒸出三氯甲烷，残渣用丙酮溶解，然后加入甲醇析出固体，过滤得到产物16.68g。(产率：93.18％)
化合物7的合成：
将1.29g 9-苯基咔唑-3-硼酸(4.50mmol)和2.00g 2-(9-溴化蒽基)-4,6-二苯基-1,3,5-三嗪(4.10mmol)加入到干净的三口烧瓶中，抽换氮气三次，然后将0.14g四-三苯基磷钯(0.12mmol)加入到烧瓶中，抽换氮气三次，随后将30毫升2M的碳酸钾溶液、30毫升的乙醇和60毫升的甲苯加入到烧瓶中，抽换氮气三次，然后110摄氏度下搅拌反应12小时，停止反应，将温度降至室温，然后用旋转蒸发仪蒸出乙醇和甲苯，残渣用水和二氯甲烷萃取三次，有机相用无水硫酸镁干燥，过滤，然后蒸出二氯甲烷，粗产物用甲苯重结晶得到产物2.40g。(产率：90.05％)
将化合物7加入含有不同比例的四氢呋喃和水的溶剂中，研究其聚集诱导效应。图3所示，化合物7在不同四氢呋喃和水的比例中表现出的聚集诱导荧光性质，从图中可以看出随着不良溶剂水的加入，其荧光强度逐渐增强，表明该化合物7具有明显的聚集诱导荧光性质。
连续对化合物7进行研磨、热恢复和溶剂熏蒸等操作，研究其压致荧光变色性质。图4所示，本实施例化合物7在压力、热恢复和溶剂熏蒸下表现出的压致荧光变色性质，从图中可以看出当对化合物进行研磨时其荧光光色发生明显的红移，而研磨后进行溶剂熏蒸化合物的光色回复原来的荧光光色，再对化合物进行研磨其荧光光色再次发生红移，再研磨的样品进行加热后化合物的光色回复到原来的荧光光色，表明该化合物7具有可回复的压致荧光变色性质。
实施例3
反应路线如下：
Figure BDA0001609882580000111
2-(9-蒽基)-4,6-二苯基-1,3,5-三嗪的合成：
将10.00g 9-蒽硼酸(45.03mmol)和13.26g 2-氯-4,6-二苯基-1,3,5-三嗪(49.54mmol)加入到干净的三口烧瓶中，抽换氮气三次，然后将0.26g四-三苯基磷钯(0.23mmol)加入到烧瓶中，抽换氮气三次，随后将60毫升2M的碳酸钾溶液、60毫升的乙醇和120毫升的甲苯加入到烧瓶中，抽换氮气三次，然后110摄氏度下搅拌反应12小时，停止反应，将温度降至室温，然后用旋转蒸发仪蒸出乙醇和甲苯，残渣用水和二氯甲烷萃取三次，有机相用无水硫酸镁干燥，过滤，然后蒸出二氯甲烷，粗产物用甲苯重结晶得到产物17.55g。(产率：95.17％)
2-(9-溴化蒽基)-4,6-二苯基-1,3,5-三嗪的合成：
将15.00g 2-(9-蒽基)-4,6-二苯基-1,3,5-三嗪(36.66mmol)、7.82g氮溴代丁二酰亚胺(43.96mmol)和400毫升三氯甲烷加入到干净的烧瓶中，抽换氮气三次，然后60摄氏度下搅拌反应1小时，停止反应，将温度降至室温，然后用旋转蒸发仪蒸出三氯甲烷，残渣用丙酮溶解，然后加入甲醇析出固体，过滤得到产物16.68g。(产率：93.18％)
化合物13的合成：
将1.29g 3-硼酸-9-苯基咔唑(4.50mmol)和2.00g 2-(9-溴化蒽基)-4,6-二苯基-1,3,5-三嗪(4.10mmol)加入到干净的三口烧瓶中，抽换氮气三次，然后将0.14g四-三苯基磷钯(0.12mmol)加入到烧瓶中，抽换氮气三次，随后将30毫升2M的碳酸钾溶液、30毫升的乙醇和60毫升的甲苯加入到烧瓶中，抽换氮气三次，然后110摄氏度下搅拌反应12小时，停止反应，将温度降至室温，然后用旋转蒸发仪蒸出乙醇和甲苯，残渣用水和二氯甲烷萃取三次，有机相用无水硫酸镁干燥，过滤，然后蒸出二氯甲烷，粗产物用甲苯重结晶得到产物2.40g。(产率：90.05％)
将化合物13加入含有不同比例的四氢呋喃和水的溶剂中，研究其聚集诱导效应。图5所示，化合物13在不同四氢呋喃和水的比例中表现出的聚集诱导荧光性质，从图中可以看出随着不良溶剂水的加入，其荧光强度逐渐增强，表明该化合物13具有明显的聚集诱导荧光性质。
连续对化合物13进行研磨、热恢复和溶剂熏蒸等操作，研究其压致荧光变色性质。图6所示，本实施例化合物13在压力、热恢复和溶剂熏蒸下表现出的压致荧光变色性质，从图中可以看出当对化合物进行研磨时其荧光光色发生明显的红移，而研磨后进行溶剂熏蒸化合物的光色回复原来的荧光光色，再对化合物进行研磨其荧光光色再次发生红移，再研磨的样品进行加热后化合物的光色回复到原来的荧光光色，表明该化合物13具有可回复的压致荧光变色性质。
实施例4
反应路线如下：
Figure BDA0001609882580000131
4-(9-蒽基)苯甲腈：
将10.00g 9-溴蒽(38.89mmol)和6.85g对氰基苯硼酸(46.67mmol)加入到干净的三口烧瓶中，抽换氮气三次，然后将0.26g四-三苯基磷钯(0.23mmol)加入到烧瓶中，抽换氮气三次，随后将60毫升2M的碳酸钾溶液、60毫升的乙醇和120毫升的甲苯加入到烧瓶中，抽换氮气三次，然后110摄氏度下搅拌反应12小时，停止反应，将温度降至室温，然后用旋转蒸发仪蒸出乙醇和甲苯，残渣用水和二氯甲烷萃取三次，有机相用无水硫酸镁干燥，过滤，然后蒸出二氯甲烷，粗产物用甲苯重结晶得到产物10.00g。(产率：92.08％)
4-(9-溴化蒽)苯甲腈的合成：
将10.00g 4-(9-蒽基)苯甲腈(35.80mmol)、7.82g氮溴代丁二酰亚胺(43.96mmol)和400毫升三氯甲烷加入到干净的烧瓶中，抽换氮气三次，然后60摄氏度下搅拌反应1小时，停止反应，将温度降至室温，然后用旋转蒸发仪蒸出三氯甲烷，残渣用丙酮溶解，然后加入甲醇析出固体，过滤得到产物12.11g。(产率：94.46％)
化合物6的合成：
将2.00g 4-硼酸-9-苯基咔唑(6.97mmol)和2.08g 4-(9-溴化蒽)苯甲腈的合成(5.80mmol)加入到干净的三口烧瓶中，抽换氮气三次，然后将0.14g四-三苯基磷钯(0.12mmol)加入到烧瓶中，抽换氮气三次，随后将30毫升2M的碳酸钾溶液、30毫升的乙醇和60毫升的甲苯加入到烧瓶中，抽换氮气三次，然后110摄氏度下搅拌反应12小时，停止反应，将温度降至室温，然后用旋转蒸发仪蒸出乙醇和甲苯，残渣用水和二氯甲烷萃取三次，有机相用无水硫酸镁干燥，过滤，然后蒸出二氯甲烷，粗产物用甲苯重结晶得到产物2.88g。(产率：95.36％)
实施例5
反应路线如下：
Figure BDA0001609882580000141
4-(9-蒽基)苯甲腈：
将10.00g 9-溴蒽(38.89mmol)和6.85g对氰基苯硼酸(46.67mmol)加入到干净的三口烧瓶中，抽换氮气三次，然后将0.26g四-三苯基磷钯(0.23mmol)加入到烧瓶中，抽换氮气三次，随后将60毫升2M的碳酸钾溶液、60毫升的乙醇和120毫升的甲苯加入到烧瓶中，抽换氮气三次，然后110摄氏度下搅拌反应12小时，停止反应，将温度降至室温，然后用旋转蒸发仪蒸出乙醇和甲苯，残渣用水和二氯甲烷萃取三次，有机相用无水硫酸镁干燥，过滤，然后蒸出二氯甲烷，粗产物用甲苯重结晶得到产物10.00g。(产率：92.08％)
4-(9-溴化蒽)苯甲腈的合成：
将10.00g 4-(9-蒽基)苯甲腈(35.80mmol)、7.82g氮溴代丁二酰亚胺(43.96mmol)和400毫升三氯甲烷加入到干净的烧瓶中，抽换氮气三次，然后60摄氏度下搅拌反应1小时，停止反应，将温度降至室温，然后用旋转蒸发仪蒸出三氯甲烷，残渣用丙酮溶解，然后加入甲醇析出固体，过滤得到产物12.11g。(产率：94.46％)
化合物12的合成：
将2.00g 9-苯基咔唑-3-硼酸(6.97mmol)和2.08g 4-(9-溴化蒽)苯甲腈的合成(5.80mmol)加入到干净的三口烧瓶中，抽换氮气三次，然后将0.14g四-三苯基磷钯(0.12mmol)加入到烧瓶中，抽换氮气三次，随后将30毫升2M的碳酸钾溶液、30毫升的乙醇和60毫升的甲苯加入到烧瓶中，抽换氮气三次，然后110摄氏度下搅拌反应12小时，停止反应，将温度降至室温，然后用旋转蒸发仪蒸出乙醇和甲苯，残渣用水和二氯甲烷萃取三次，有机相用无水硫酸镁干燥，过滤，然后蒸出二氯甲烷，粗产物用甲苯重结晶得到产物2.88g。(产率：95.36％)
实施例6
反应路线如下：
Figure BDA0001609882580000161
4-(9-蒽基)苯甲腈：
将10.00g 9-溴蒽(38.89mmol)和6.85g对氰基苯硼酸(46.67mmol)加入到干净的三口烧瓶中，抽换氮气三次，然后将0.26g四-三苯基磷钯(0.23mmol)加入到烧瓶中，抽换氮气三次，随后将60毫升2M的碳酸钾溶液、60毫升的乙醇和120毫升的甲苯加入到烧瓶中，抽换氮气三次，然后110摄氏度下搅拌反应12小时，停止反应，将温度降至室温，然后用旋转蒸发仪蒸出乙醇和甲苯，残渣用水和二氯甲烷萃取三次，有机相用无水硫酸镁干燥，过滤，然后蒸出二氯甲烷，粗产物用甲苯重结晶得到产物10.00g。(产率：92.08％)
4-(9-溴化蒽)苯甲腈的合成：
将10.00g 4-(9-蒽基)苯甲腈(35.80mmol)、7.82g氮溴代丁二酰亚胺(43.96mmol)和400毫升三氯甲烷加入到干净的烧瓶中，抽换氮气三次，然后60摄氏度下搅拌反应1小时，停止反应，将温度降至室温，然后用旋转蒸发仪蒸出三氯甲烷，残渣用丙酮溶解，然后加入甲醇析出固体，过滤得到产物12.11g。(产率：94.46％)
化合物18的合成：
将2.00g 3-硼酸-9-苯基咔唑(6.97mmol)和2.08g 4-(9-溴化蒽)苯甲腈的合成(5.80mmol)加入到干净的三口烧瓶中，抽换氮气三次，然后将0.14g四-三苯基磷钯(0.12mmol)加入到烧瓶中，抽换氮气三次，随后将30毫升2M的碳酸钾溶液、30毫升的乙醇和60毫升的甲苯加入到烧瓶中，抽换氮气三次，然后110摄氏度下搅拌反应12小时，停止反应，将温度降至室温，然后用旋转蒸发仪蒸出乙醇和甲苯，残渣用水和二氯甲烷萃取三次，有机相用无水硫酸镁干燥，过滤，然后蒸出二氯甲烷，粗产物用甲苯重结晶得到产物2.88g。(产率：95.36％)
实施例7
蒽基荧光材料用于制作传感器和/或光电功能器件。
例如，用以检测离子、气体、有机小分子、爆炸物、蛋白、酶等化学/生物传感器，向传统的聚集引起猝灭化合物引入该材料，制备高效固态发光器件等。
尽管结合实施例对本发明进行了说明，但本发明并不局限于上述实施例，应当理解，在本发明构思的引导下，所作的任何修改、等同替换、改进等，均应包含在本发明的保护范围之内。

Claims (4)

1.一种具有聚集诱导荧光和压致荧光变色性质的蒽基荧光材料，其特征在于，其结构通式如下列结构式：
Figure FDA0002603630520000011
其中，D为给电子基团；A为吸电子基团；
所述D是下列基团2a、2c中的一种：
Figure FDA0002603630520000012
其中，*为与蒽连接的位点；
所述A是取代或未取代的基团3a：
Figure FDA0002603630520000013
其中，*为与蒽连接的位点。
2.根据权利要求1所述的具有聚集诱导荧光和压致荧光变色性质的蒽基荧光材料，其特征在于，所述蒽基荧光材料为下列化合物中的任一种：
Figure FDA0002603630520000021
3.一种如权利要求1或2所述的具有聚集诱导荧光和压致荧光变色性质的蒽基荧光材料的制备方法，其特征在于，合成路线为：
第一步：
Figure FDA0002603630520000022
或者
Figure FDA0002603630520000023
第二步：
Figure FDA0002603630520000024
其中，D为给电子基团；A为吸电子基团。
4.一种如权利要求1或2所述的具有聚集诱导荧光和压致荧光变色性质的蒽基荧光材料的应用，其特征在于，所述蒽基荧光材料用于制作传感器和/或光电功能器件。
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