CN114478221A - 基于芘的aie类荧光探针及其制备方法和应用 - Google Patents

基于芘的aie类荧光探针及其制备方法和应用 Download PDF

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CN114478221A
CN114478221A CN202210175325.8A CN202210175325A CN114478221A CN 114478221 A CN114478221 A CN 114478221A CN 202210175325 A CN202210175325 A CN 202210175325A CN 114478221 A CN114478221 A CN 114478221A
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fluorescent probe
pyrene
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刘勇
周正
张学琪
王强
赵德川
杨在君
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Abstract

本发明提供一种基于芘的新型AIE荧光探针及其制备方法和应用，属于荧光探针的合成技术领域，AIE荧光探针结构式如下：
Figure DDA0003519993230000011
其制备方法是以苄叉丙酮(或其衍生物
Figure DDA0003519993230000012
)和芘甲醛为原料，加入10％的氢氧化钠溶液(或哌啶)，在乙醇中混合反应2～10小时，反应温度30‑60℃，反应完毕后，用冰水将反应淬灭，并用1N盐酸调节溶液的pH值至弱碱性或中性，真空过滤，所得滤渣经硅胶柱层析分离提纯得荧光探针。本发明提供的一系列基于芘的AIE荧光探针结构新颖，光稳定性好，制备方法简单，操作方便，在荧光墨水、荧光检测和生物成像等方面具有广阔的应用前景。

Description

基于芘的AIE类荧光探针及其制备方法和应用
技术领域
本发明涉及一系列聚集诱导发光(AIE)荧光探针，具体为基于芘的AIE类荧光探针及其制备方法和应用。
背景技术
荧光探针具有灵敏度高、技术简单、无侵入性等优点，已在分析传感、光学材料和生物成像领域成为一种极具吸引力的通用工具。然而，大部分的荧光材料在聚集状态下会产生聚集荧光淬灭(ACQ)效应，这大大的限制了其实际应用。聚集诱导发光(AIE)分子的出现有效解决了ACQ这一问题，与传统的荧光材料相比，AIE分子在高浓度甚至是固体状态下仍然可以保持高荧光发射。与ACQ分子相比，AIE分子在聚集态下具有发光效率高、光稳定性好、斯托克斯位移大和背景噪声低等独特优势，已被广泛应用于荧光检测、病毒检测、食品质量监测、光电器件、生物成像和癌症诊疗等众多领域，应用前景广阔并且极具商机。因此，开发新型AIE分子具有重要的研究价值和实际应用潜力。
近年来，荧光探针发展非常迅猛，许多类型的荧光探针被设计和合成，其中部分荧光探针仍然存在一些缺点，例如，荧光探针合成复杂、只能单一性识别一种离子、发射波长较短、自身溶解性不好、光稳定性差等等。以上诸多不足限制了荧光探针的应用范围和实际应用价值。
芘具有共轭体系大、紫外吸收系数大、荧光量子产率高等优点，并且具有单体和激基缔合物两种发射波长，是构建荧光探针的理想荧光团，因此经常被用作荧光团来设计合成荧光探针。但基于芘的AIE类荧光探针还相对较少，尤其是具有长波长的芘类AIE荧光探针。
因此，开发出一种新的基于芘的AIE类荧光探针具有非常重要的意义。
发明内容
为了解决上述技术问题，本发明提供一种工艺简单、原料易得、成本低的基于芘的AIE类荧光探针及其制备方法和应用。
为了实现上述目的，本发明进一步的技术方案为：
较为具体地，本发明第一方面提供了基于芘的AIE荧光探针，其特征在于，该探针的结构式如下所示：
Figure BDA0003519993210000021
其中，所述取代基R为：苯基、4-甲氧基苯基、4-甲基苯基、4-羟基苯基、4-氯苯基、4-溴苯基、4-硝基苯基、4-氰基苯基、4-三氟甲基苯基、4-吡啶基、4-二甲胺基苯基、4-二乙胺基苯基、4-二苯胺基苯基、4-二对甲苯胺基苯基、4-(4-吡啶基)苯基、4-(甲基巯基)苯基、4-(4-吗啉)苯基、4-[双(4-甲氧基苯基)氨基]苯基、4-(羟甲基)苯基、4-吡啶鎓基、4-(4-吡啶鎓基)苯基、4-羧基苯基、4-磷酸基苯基、4-硼酸基苯基、4-苯硼酸基苯基、4-苯硼酸基吡啶鎓基、3-甲氧基苯基、3-甲基苯基、3-羟基苯基、3-氯苯基、3-溴苯基、3-硝基苯基、3-吡啶基、2-甲氧基苯基、2-甲基苯基、2-羟基苯基、2-氯苯基、2-溴苯基、2-噻吩基、2-呋喃基、5-甲基-2-噻吩、2-萘基、9-蒽基、芘基中的一种。
较为具体地，本发明第二方面提供了一种基于芘的AIE荧光探针的制备方法，其特征在于，包含以下步骤：
S1:以苄叉丙酮或其衍生物
Figure BDA0003519993210000022
和芘甲醛为原料，加入反应容器中；
S2:接着在反应容器中加入乙醇，使原料溶解；
S3:在溶解后的溶液中加入10％的氢氧化钠溶液(或哌啶)，混合反应2～10小时；
S4:反应完毕后，冷却至室温，将反应淬灭，用1N盐酸调节溶液的pH值至弱碱性或中性；
S5:真空过滤并分离提纯后得到荧光探针；
反应通式为：
Figure BDA0003519993210000031
进一步，所述步骤S1中，苄叉丙酮衍生物和芘甲醛的物质的量之比为1:1～1:1.3。
进一步，所述步骤S3中，反应温度为30-60℃。
进一步，所述步骤S5中，所述真空过滤后的滤渣经硅胶柱层析分离提纯得荧光探针。
较为具体地，本发明第三方面提供了一种基于芘的AIE荧光探针在荧光墨水方面的应用。
较为具体地，本发明第四方面提供了一种以非诊断和非治疗目的的基于芘的AIE荧光探针在检测生物体内硫醇含量方面的应用。
较为具体地，本发明第五方面提供了一种基于芘的AIE荧光探针在生物成像方面的应用，为生物学研究奠定了很大的基础。
与现有技术相比，本发明具有如下有益效果：
1)本发明提供的荧光探针通过商品可得的原料经过一步或者两步反应就得到了目标产物，操作过程简单，不需要无水无氧和高温高压等条件。
2)本发明提供的荧光探针对光、热及pH值等条件都具有良好的稳定性。
3)本发明提供的荧光探针斯托克斯位移大，具有典型的AIE效应。
4)本发明制备方法简单，原料易得，合成工艺成熟，成本较低，适合工业化大规模生产。因此，在技术应用和日常生活中有着广阔的应用前景。
附图说明
图1是本发明实施例所制备荧光探针的1HNMR谱图。
图2是本发明实施例所制备的荧光探针溶液书写在滤纸上的文字在紫外灯下和日光灯下的对比图。
具体实施方式
为了使本技术领域的人员更好地理解本发明方案，下面将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的实施例，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在没有做出创造性劳动前提下所获得的所有其他实施例，都应当属于本发明保护的范围。
本发明提供了一种基于芘的AIE荧光探针，其特征在于，该探针的结构式如下所示：
Figure BDA0003519993210000041
其中，所述取代基R为：苯基、4-甲氧基苯基、4-甲基苯基、4-羟基苯基、4-氯苯基、4-溴苯基、4-硝基苯基、4-氰基苯基、4-三氟甲基苯基、4-吡啶基、4-二甲胺基苯基、4-二乙胺基苯基、4-二苯胺基苯基、4-二对甲苯胺基苯基、4-(4-吡啶基)苯基、4-(甲基巯基)苯基、4-(4-吗啉)苯基、4-[双(4-甲氧基苯基)氨基]苯基、4-(羟甲基)苯基、4-吡啶鎓基、4-(4-吡啶鎓基)苯基、4-羧基苯基、4-磷酸基苯基、4-硼酸基苯基、4-苯硼酸基苯基、4-苯硼酸基吡啶鎓基、3-甲氧基苯基、3-甲基苯基、3-羟基苯基、3-氯苯基、3-溴苯基、3-硝基苯基、3-吡啶基、2-甲氧基苯基、2-甲基苯基、2-羟基苯基、2-氯苯基、2-溴苯基、2-噻吩基、2-呋喃基、5-甲基-2-噻吩、2-萘基、9-蒽基、芘基中的一种。
基于芘的AIE荧光探针的制备方法，包含以下步骤：
S1:以苄叉丙酮或其衍生物和芘甲醛为原料，加入反应容器中，苄叉丙酮衍生物和芘甲醛的物质的量之比为1:1～1:1.3；
S2:接着在反应容器中加入乙醇，使原料溶解；
S3:在溶解后的溶液中加入10％的氢氧化钠溶液(或哌啶)，混合反应2～10小时，反应温度为30-60℃；
S4:反应完毕后，冷却至室温，将反应淬灭，用1N盐酸调节溶液的pH值至弱碱性或中性；
S5:真空过滤并分离提纯后得到荧光探针，所述真空过滤后的滤渣经硅胶柱层析分离提纯得荧光探针。
实施例1
在50mL圆底烧瓶中先加入干净的搅拌子，然后依次加入苄叉丙酮(146.2mg,1.0mmol)和芘甲醛(230.2mg,1.0mmol)，用乙醇(5.0mL)溶解，最后缓慢滴加10％的氢氧化钠溶液(1.0mL)，体系在50℃油浴中搅拌(6h)。TLC跟踪监测至原料消耗完全，体系冷却至室温，用冰水将反应淬灭，并用1N盐酸调节溶液的pH值到中性，真空抽滤，用少量冷水洗涤滤渣三次，所得滤渣经硅胶柱层析分离提纯，真空干燥后得荧光探针。
所制备荧光探针的谱图如图1所示，分子结构式如下：
Figure BDA0003519993210000051
实施例2
在50mL圆底烧瓶中先加入干净的搅拌子，然后依次加入4-(2-萘基)丁-3-烯-2-酮(196.3mg,1.0mmol)和芘甲醛(230.3mg,1.0mmol)，用乙醇(5.0mL)溶解，最后缓慢滴加10％的氢氧化钠溶液(1.0mL)，体系在60℃油浴中搅拌10h。TLC跟踪监测至原料消耗完全，体系冷却至室温，用冰水将反应淬灭，并用1N盐酸调节溶液的pH值到中性，真空抽滤，用少量冷水洗涤滤渣三次，所得滤渣经硅胶柱层析分离提纯，真空干燥后得荧光探针。
所制备荧光探针的分子结构式如下：
Figure BDA0003519993210000052
实施例3
在50mL圆底烧瓶中先加入干净的搅拌子，然后依次加入4-甲氧基苄叉丙酮(176.2mg,1.0mmol)和芘甲醛(230.3mg,1.0mmol)，用乙醇(5.0mL)溶解，最后缓慢滴加10％的氢氧化钠溶液(1.0mL)，体系在50℃油浴中搅拌6h。TLC跟踪监测至原料消耗完全，体系冷却至室温，用冰水将反应淬灭，并用1N盐酸调节溶液的pH值到中性，真空抽滤，用少量冷水洗涤滤渣三次，所得滤渣经硅胶柱层析分离提纯，真空干燥后得荧光探针。
所制备荧光探针的分子结构式如下：
Figure BDA0003519993210000061
实施例4
在50mL圆底烧瓶中先加入干净的搅拌子，然后依次加入4-甲硫基苄叉丙酮(192.3mg,1.0mmol)和芘甲醛(230.3mg,1.0mmol)，用乙醇(5.0mL)溶解，最后缓慢滴加10％的氢氧化钠溶液(1.0mL)，体系在50℃油浴中搅拌6h。TLC跟踪监测至原料消耗完全，体系冷却至室温，用冰水将反应淬灭，并用1N盐酸调节溶液的pH值到中性，真空抽滤，用少量冷水洗涤滤渣三次，所得滤渣经硅胶柱层析分离提纯，真空干燥后得荧光探针。
所制备荧光探针的分子结构式如下：
Figure BDA0003519993210000062
实施例5
在50mL圆底烧瓶中先加入干净的搅拌子，然后依次加入4-二甲胺基苄叉丙酮(160.9mg,1.0mmol)和芘甲醛(241.8mg,1.05mmol)，用乙醇(5.0mL)溶解，最后缓慢滴加10％的氢氧化钠溶液(1.0mL)，体系在60℃油浴中搅拌8h。TLC跟踪监测至原料消耗完全，体系冷却至室温，用冰水将反应淬灭，并用1N盐酸调节溶液的pH值到弱碱性，真空抽滤，用少量冷水洗涤滤渣三次，所得滤渣经硅胶柱层析分离提纯，真空干燥后得荧光探针。
所制备荧光探针的分子结构式如下：
Figure BDA0003519993210000071
实施例6
在50mL圆底烧瓶中先加入干净的搅拌子，然后依次加入4-二苯胺基苄叉丙酮(313.4mg,1.0mmol)和芘甲醛(241.8mg,1.05mmol)，用乙醇(5.0mL)溶解，最后缓慢滴加10％的氢氧化钠溶液(1.0mL)，体系在60℃油浴中搅拌10h。TLC跟踪监测至原料消耗完全，体系冷却至室温，用冰水将反应淬灭，并用1N盐酸调节溶液的pH值到弱碱性，真空抽滤，用少量冷水洗涤滤渣三次，所得滤渣经硅胶柱层析分离提纯，真空干燥后得荧光探针。
所制备荧光探针的分子结构式如下：
Figure BDA0003519993210000072
实施例7
在50mL圆底烧瓶中先加入干净的搅拌子，然后依次加入4-二对甲苯胺基苄叉丙酮(341.5mg,1.0mmol)和芘甲醛(299.4mg,1.30mmol)，用乙醇(5.0mL)溶解，最后缓慢滴加10％的氢氧化钠溶液(1.0mL)，体系在60℃油浴中搅拌10h。TLC跟踪监测至原料消耗完全，体系冷却至室温，用冰水将反应淬灭，并用1N盐酸调节溶液的pH值到弱碱性，真空抽滤，用少量冷水洗涤滤渣三次，所得滤渣经硅胶柱层析分离提纯，真空干燥后得荧光探针。
所制备荧光探针的分子结构式如下：
Figure BDA0003519993210000073
实施例8
在50mL圆底烧瓶中先加入干净的搅拌子，然后依次加入4-吗啉基苄叉丙酮(231.3mg,1.0mmol)和芘甲醛(241.8mg,1.05mmol)，用乙醇(5.0mL)溶解，最后缓慢滴加10％的氢氧化钠溶液(1.0mL)，体系在60℃油浴中搅拌8h。TLC跟踪监测至原料消耗完全，体系冷却至室温，用冰水将反应淬灭，并用1N盐酸调节溶液的pH值到弱碱性，真空抽滤，用少量冷水洗涤滤渣三次，所得滤渣经硅胶柱层析分离提纯，真空干燥后得荧光探针。
所制备荧光探针的分子结构式如下：
Figure BDA0003519993210000081
实施例9
在50mL圆底烧瓶中先加入干净的搅拌子，然后依次加入4-溴苄叉丙酮(225.1mg,1.0mmol)和芘甲醛(230.3mg,1.0mmol)，用乙醇(5.0mL)溶解，最后缓慢滴加10％的氢氧化钠溶液(1.0mL)，体系在50℃油浴中搅拌4h。TLC跟踪监测至原料消耗完全，体系冷却至室温，用冰水将反应淬灭，并用1N盐酸调节溶液的pH值到中性，真空抽滤，用少量冷水洗涤滤渣三次，所得滤渣经硅胶柱层析分离提纯，真空干燥后得荧光探针。
所制备荧光探针的分子结构式如下：
Figure BDA0003519993210000082
实施例10
在50mL圆底烧瓶中先加入干净的搅拌子，然后依次加入4-三氟甲基苄叉丙酮(214.2mg,1.0mmol)和芘甲醛(230.3mg,1.0mmol)，用乙醇(5.0mL)溶解，最后缓慢滴加10％的氢氧化钠溶液(1.0mL)，体系在30℃油浴中搅拌2h。TLC跟踪监测至原料消耗完全，体系冷却至室温，用冰水将反应淬灭，并用1N盐酸调节溶液的pH值到中性，真空抽滤，用少量冷水洗涤滤渣三次，所得滤渣经硅胶柱层析分离提纯，真空干燥后得荧光探针。
所制备荧光探针的分子结构式如下：
Figure BDA0003519993210000091
实施例11
在50mL圆底烧瓶中先加入干净的搅拌子，然后依次加入4-(4-吡啶基)丁-3-烯-2-酮(147.2mg,1.0mmol)和芘甲醛(253.3mg,1.1mmol)，用乙醇(5.0mL)溶解，最后缓慢滴加哌啶(5滴)，体系在60℃油浴中搅拌10h。TLC跟踪监测至原料消耗完全，体系冷却至室温，用冰水将反应淬灭，真空抽滤，用少量冷水洗涤滤渣三次，所得滤渣经硅胶柱层析分离提纯，真空干燥后得荧光探针。
所制备荧光探针的分子结构式如下：
Figure BDA0003519993210000092
实施例12
在50mL圆底烧瓶中先加入干净的搅拌子，然后依次加入4-(2-呋喃基)丁-3-烯-2-酮(136.2mg,1.0mmol)和芘甲醛(230.3mg,1.0mmol)，用乙醇(5.0mL)溶解，最后缓慢滴加10％的氢氧化钠溶液(1.0mL)，体系在50℃油浴中搅拌8h。TLC跟踪监测至原料消耗完全，体系冷却至室温，用冰水将反应淬灭，并用1N盐酸调节溶液的pH值到中性，真空抽滤，用少量冷水洗涤滤渣三次，所得滤渣经硅胶柱层析分离提纯，真空干燥后得荧光探针。
所制备荧光探针的分子结构式如下：
Figure BDA0003519993210000093
实施例13
在50mL圆底烧瓶中先加入干净的搅拌子，然后依次加入4-(2-噻吩基)丁-3-烯-2-酮(152.2mg,1.0mmol)和芘甲醛(230.3mg,1.0mmol)，用乙醇(5.0mL)溶解，最后缓慢滴加10％的氢氧化钠溶液(1.0mL)，体系在50℃油浴中搅拌8h。TLC跟踪监测至原料消耗完全，体系冷却至室温，用冰水将反应淬灭，并用1N盐酸调节溶液的pH值到中性，真空抽滤，用少量冷水洗涤滤渣三次，所得滤渣经硅胶柱层析分离提纯，真空干燥后得荧光探针。
所制备荧光探针的分子结构式如下：
Figure BDA0003519993210000101
实施例14
在50mL圆底烧瓶中先加入干净的搅拌子，然后依次加入4-(5-甲基2-噻吩基)丁-3-烯-2-酮(166.2mg,1.0mmol)和芘甲醛(230.3mg,1.0mmol)，用乙醇(5.0mL)溶解，最后缓慢滴加10％的氢氧化钠溶液(1.0mL)，体系在50℃油浴中搅拌8h。TLC跟踪监测至原料消耗完全，体系冷却至室温，用冰水将反应淬灭，并用1N盐酸调节溶液的pH值到中性，真空抽滤，用少量冷水洗涤滤渣三次，所得滤渣经硅胶柱层析分离提纯，真空干燥后得荧光探针。
所制备荧光探针的分子结构式如下：
Figure BDA0003519993210000102
实施例15
所用1.0mmol的苄叉丙酮衍生物
Figure BDA0003519993210000103
与芘甲醛，其他实验方法和条件同实施例1，得一系列荧光探针。
所用实施例中的苄叉丙酮衍生物取代基R为：苯基、4-甲氧基苯基、4-甲基苯基、4-羟基苯基、4-氯苯基、4-溴苯基、4-硝基苯基、4-氰基苯基、4-三氟甲基苯基、4-吡啶基、4-二甲胺基苯基、4-二乙胺基苯基、4-二苯胺基苯基、4-二对甲苯胺基苯基、4-(4-吡啶基)苯基、4-(甲基巯基)苯基、4-(4-吗啉)苯基、4-[双(4-甲氧基苯基)氨基]苯基、4-(羟甲基)苯基、4-吡啶鎓基、4-(4-吡啶鎓基)苯基、4-羧基苯基、4-磷酸基苯基、4-硼酸基苯基、4-苯硼酸基苯基、4-苯硼酸基吡啶鎓基、3-甲氧基苯基、3-甲基苯基、3-羟基苯基、3-氯苯基、3-溴苯基、3-硝基苯基、3-吡啶基、2-甲氧基苯基、2-甲基苯基、2-羟基苯基、2-氯苯基、2-溴苯基、2-噻吩基、2-呋喃基、5-甲基-2-噻吩、2-萘基、9-蒽基、芘基等中的一种。
实施例16
本发明提供了所述的一系列基于芘的AIE荧光探针在荧光墨水方面的应用。该类荧光探针具有很强的荧光发射，可以作为一种新型的荧光墨水使用，具有广阔的应用前景。将本发明提供的荧光探针的均相水溶液(10μM)注射到一支空笔芯中，直接作为荧光墨水在滤纸上写字和图案，所写字体和图案在365nm紫外光照射下发出明亮荧光，与背景颜色有明显的区别，如图2所示。
实施例17
本发明提供了所述的一系列基于芘的AIE荧光探针在荧光检测方面的应用。该类荧光探针可以用于检测生物体内硫醇(例如GSH、Cys和Hcy)的含量。GSH/Cys/Hcy中巯基亲核加成进攻该类荧光探针中的碳碳双键，破坏该类探针的空间效应，使该类探针发出荧光信号。荧光光谱实验表明，该类荧光探针具有很好的选择性、较高的灵敏度，可作为体外实时测定GSH/Cys/Hcy浓度的有效工具。
实施例18
本发明提供了所述的一系列基于芘的AIE荧光探针在生物成像方面的应用。该类荧光探针具有很强的荧光发射，且部分具有内质网、线粒体、溶酶体、葡萄糖等靶向基团，在细胞、细菌和斑马鱼中能很好地成像，为生物学研究奠定了很大的基础。
利用本发明所述技术方案，或本领域的技术人员在本发明技术方案的启发下，设计出类似的技术方案，而达到上述技术效果的，均是落入本发明的保护范围。

Claims (8)

1.基于芘的AIE荧光探针，其特征在于，该探针的结构式如下所示：
Figure FDA0003519993200000011
其中，
所述取代基R为：苯基、4-甲氧基苯基、4-甲基苯基、4-羟基苯基、4-氯苯基、4-溴苯基、4-硝基苯基、4-氰基苯基、4-三氟甲基苯基、4-吡啶基、4-二甲胺基苯基、4-二乙胺基苯基、4-二苯胺基苯基、4-二对甲苯胺基苯基、4-(4-吡啶基)苯基、4-(甲基巯基)苯基、4-(4-吗啉)苯基、4-[双(4-甲氧基苯基)氨基]苯基、4-(羟甲基)苯基、4-吡啶鎓基、4-(4-吡啶鎓基)苯基、4-羧基苯基、4-磷酸基苯基、4-硼酸基苯基、4-苯硼酸基苯基、4-苯硼酸基吡啶鎓基、3-甲氧基苯基、3-甲基苯基、3-羟基苯基、3-氯苯基、3-溴苯基、3-硝基苯基、3-吡啶基、2-甲氧基苯基、2-甲基苯基、2-羟基苯基、2-氯苯基、2-溴苯基、2-噻吩基、2-呋喃基、5-甲基-2-噻吩、2-萘基、9-蒽基、芘基中的一种。
2.根据权利要求1所述的基于芘的AIE荧光探针的制备方法，其特征在于，包含以下步骤：
S1:以苄叉丙酮或其衍生物和芘甲醛为原料，加入反应容器中；
S2:接着在反应容器中加入乙醇，使原料溶解；
S3:在溶解后的溶液中加入10％的氢氧化钠溶液或哌啶，混合反应2～10小时；
S4:反应完毕后，冷却至室温，将反应淬灭，用1N盐酸调节溶液的pH值至弱碱性或中性；
S5:真空过滤并分离提纯后得到荧光探针。
3.如权利要求2所述的方法，其特征在于，所述步骤S1中，苄叉丙酮衍生物和芘甲醛的物质的量之比为1:1～1:1.3。
4.如权利要求2所述的方法，其特征在于，所述步骤S3中，反应温度为30-60℃。
5.如权利要求4所述的方法，其特征在于，所述步骤S5中，所述真空过滤后的滤渣经硅胶柱层析分离提纯得荧光探针。
6.如权利要求1所述的基于芘的AIE荧光探针在荧光墨水方面的应用。
7.如权利要求1所述的以非诊断和非治疗目的的基于芘的AIE荧光探针在检测生物体内硫醇含量方面的应用。
8.如权利要求1所述的基于芘的AIE荧光探针在生物成像方面的应用。
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