CN118834197A - 一种可见光调控荧光点亮型二芳基乙烯有机化合物及其制备方法和应用 - Google Patents
一种可见光调控荧光点亮型二芳基乙烯有机化合物及其制备方法和应用 Download PDFInfo
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Abstract
本发明公开了一种可见光调控高荧光量子产率荧光点亮型二芳基乙烯有机化合物及其制备方法，该荧光点亮型二芳基乙烯有机化合物结构如通式(1)所示，通式(1)中，R1表示为芳香族官能团。本发明所有荧光点亮型二芳基乙烯光致变色材料都可以实现可见光驱动开环体到闭环体转换并且闭环体下都具有极高的荧光量子产率。
Description
技术领域
本发明涉及光致变色材料，特别涉及新型可见光驱动高荧光量子产率荧光点亮型二芳基乙烯光致变色材料。
背景技术
荧光turn-on型二芳基乙烯分子开关因其在开环状态无荧光而闭环状态呈现荧光的独特光物理特性，近年来被广泛应用于传感、门控、防伪及生物体超分辨显微成像等领域，具有广阔的商业价值。然而，当前大部分荧光点亮型二芳基乙烯分子开环体无论在固态还是溶液中其吸收只坐落在紫外区，导致该类分子只能在紫外光的照射下才能发生从开环体到闭环体的转换。另外，绝大部分荧光点亮型二芳基乙烯分子其闭环体荧光量子产率普遍较低，限制了其在超分辨荧光成像领域的应用。由于，一方面紫外光会对分子本身稳定性造成影响，长时间的紫外光照射势必会引起不可控的光化学副反应从而导致分子老化；另一方面较低的荧光量子产率会导致生物体超分辨荧光成像时信噪比增大，导致成像效果较差。因此，开发可见光驱动开环体到闭环体光环化转换的高荧光量子产率荧光点亮型二芳基乙烯分子具有重要意义。
发明内容
针对现有技术存在的上述问题，本发明提供了一种二芳基乙烯有机化合物及、其制备方法及其在可见光调控荧光点亮型材料中的应用，该材料可以在可见光驱动下实现开环体到闭环体的转换，并且具有更高的荧光量子产率。
本发明的技术方案如下：
一种荧光点亮型二芳基乙烯有机化合物，结构如通式(1)所示：
通式(1)中，R1为取代或者未取代的芳基，所述芳基上的取代基选自C1～C4烷基、C1～C4烷氧基、取代氨基、三氟甲基中的一个或者多个。
本发明通过在已有荧光点亮型二芳基乙烯分子骨架上6与6’位连接芳香环的策略，即可以增大分子的共轭程度致使开环体吸收边红移至可见光区，也可以提高分子闭环体下吸收强度(即增大振子强度)，从而获得一种可以实现可见光驱动高荧光量子产率荧光点亮型二芳基乙烯光致变色材料。
作为优选，R1为取代或者未取代的苯基，所述苯基上的取代基选自C1～C4烷基、C1～C4烷氧基中的一个或者多个。
作为优选，通式(1)中R1表示下列结构中的一种：
作为优选，所述的可见光驱动高荧光量子产率荧光点亮型二芳基乙烯有机化合物，为以下具体化合物中的一种：
作为优选，所述的荧光点亮型二芳基乙烯有机化合物为化合物1，2或5，结构式如下：
本发明还提供了一种所述的荧光点亮型二芳基乙烯有机化合物的制备方法，包括：
在惰性气氛下，碘代化合物与硼酸化合物用四氢呋喃溶解，再加入Pd(PPh3)4和饱和碳酸钾溶液，将上述反应物的混合溶液于回流条件下，反应12～24h；反应混合物冷却至室温后，乙酸乙酯萃取，合并有机相，无水Na2SO4干燥后旋干；经硅胶柱层析纯化，得到目标产物；
反应式如下：
作为优选，所述碘代化合物与硼酸类化合物的摩尔比为1:2.4～2.6，Pd(PPh3)4与硼酸类化合物的摩尔比为0.1:0.9～1.1，饱和碳酸钾溶液与四氢呋喃的体积比为0.5:0.9～1.1。
同现有技术相比，本发明有益的技术效果在于：
本发明化合物基于芳香环及其衍生物连接在Me-BTTO4分子骨架6与6’位构筑。6与6’位连接芳香环之后，会导致开环体状态下HOMO-LUMO之间带隙降低，导致开环体吸收光谱发生红移，吸收边坐落在可见光区，从而实现可见光驱动光环化反应。另外，芳香环引入之后闭环体的吸收强度也较分子骨架显著增强，即分子的振子强度增大，从而实现荧光量子产率的增强。并且，上述结果均已通过密度泛函理论计算与实验验证，此类新型二芳基乙烯分子具有极好的应用前景。
具体实施方式
下面结合实施例，对本发明进行具体描述。
实施例1：化合物1的合成：
合成路线：
在50mL双颈烧瓶中，依次加入中间体碘代Me-BTTO4(0.21g，0.30mmol)、2-甲基苯硼酸(0.10g，0.72mmol)和10mL四氢呋喃溶液并搅拌溶解，再加入5mL K2CO3饱和溶液与Pd(PPh3)4(0.09g，0.08mmol)。氮气将溶液脱气约15分钟后回流8小时。反应混合物冷却至室温后，乙酸乙酯萃取，合并有机相，无水Na2SO4干燥后旋干。经硅胶柱层析(DCM/hexane＝1:3)纯化得到1(0.16g，85％)。1H NMR(400MHz,CDCl3)：δ[ppm]1.99-1.25(t,6H),2.23-2.27(m,9H),7.30-7.63(m,9H),7.76(d,J＝4Hz,3H),7.82(s,1H),7.93(t,J＝8Hz,1H),8.22-8.26(m,1H)；13C NMR(100MHz,CDCl3):δ[ppm]146.44,138.90,137.38,137.19,135.30,132.12,130.01,129.86,127.64,127.56,126.94,126.67,125.38,125.08,122.77,122.23,121.99,121.94,18.3,15.7,8.61,8.33.HRMS[M+H]+calcd.for C37H30O4S3:634.1306,found634.1463.
实施例2：化合物2的合成：
合成路线：
在50mL双颈烧瓶中，依次加入碘代Me-BTTO4(0.21g，0.30mmol)、2，6-二甲基苯硼酸(0.11g，0.72mmol)和10mL四氢呋喃溶液并搅拌溶解，再加入5mL K2CO3饱和溶液与Pd(PPh3)4(0.09g，0.08mmol)。氮气将溶液脱气约15分钟后回流8小时。反应混合物冷却至室温后，乙酸乙酯萃取，合并有机相，无水Na2SO4干燥后旋干。经硅胶柱层析(DCM/hexane＝1:3)纯化得到2(0.16g，83％)。1H NMR(400MHz,CDCl3):δ[ppm]1.92-2.24(m,6H),2.25-2.29(m,15H),7.51-7.62(m,7H),7.90-7.92(m,2H),7.96(m,2H),8.25-8.27(m,1H),8.41(d,J＝4Hz,1H)；13C NMR(100MHz,CDCl3)：δ[ppm]148.42,140.38,140.04,136.42,134.91,132.17,129.98,129.84,128.90,127.53,124.84,124.64,123.73,123.09,121.97,121.94,121.82,118.91,18.3,15.7,8.60,8.28.HRMS[M+H]+calcd.for C39H34O4S3:662.1619,found662.1721.
实施例3：化合物5的合成：
合成路线：
在50mL双颈烧瓶中，依次加入碘代Me-BTTO4(0.21g，0.30mmol)、4-甲氧基苯硼酸(0.11g，0.72mmol)和10mL四氢呋喃溶液并搅拌溶解，再加入5mL K2CO3饱和溶液与Pd(PPh3)4(0.09g，0.08mmol)。氮气将溶液脱气约15分钟后回流8小时。反应混合物冷却至室温后，乙酸乙酯萃取，合并有机相，无水Na2SO4干燥后旋干。经硅胶柱层析(DCM/hexane＝1:3)纯化得到2(0.14g，80％)。1H NMR(400MHz,CDCl3):δ[ppm]1.90-2.22(m,6H),5.82(d,J＝8Hz,6H)；7.30-7.61(m,9H),7.76(d,J＝8Hz,3H),7.88-7.90(m,1H),8.15-8.24(m,2H)；13CNMR(100MHz,CDCl3)：δ[ppm]148.04,140.59,139.97,136.19,134.87,132.13,130.82,130.00,129.86,127.44,124.87,124.77,122.99,122.63,122.37,121.97,121.93,120.16,55.9,55.8,8.59,8.28.HRMS[M+H]+calcd.for C37H30O6S3:667.1205,found667.1199.
对本发明化合物1,2及5开环体与闭环体还分别对垂直吸收能、振子强度、HOMO/LUMO能级以及HOMO/LUMO之间带隙进行了量化计算；对最大发射、荧光量子产率、荧光寿命以及S1能级进行了测试，结果如表1所示。
表1：1、2与5分子的理论计算与实验数据
上述试验结果表明，本申请的化合物1、化合物2和化合物5开环体吸收光谱吸收边坐落在可见光区，同时，闭环体具有极高的荧光量子效率，可以成功实现可见光驱动光环化及高荧光量子产率，具有较好的应用前景。
虽然已通过实施例和优选实施方式公开了本发明，但应理解，本发明不限于所公开的实施方式。相反，本领域技术人员应明白，其意在涵盖各种变型和类似的安排。因此，所附权利要求的范围应与最宽的解释相一致以涵盖所有这样的变型和类似的安排。
Claims (9)
1.一种二芳基乙烯有机化合物，其特征在于，结构如通式(1)所示：
通式(1)中，R1为取代或者未取代的芳基，所述芳基上的取代基选自C1～C4烷基、C1～C4烷氧基、取代氨基、三氟甲基中的一个或者多个。
2.根据权利要求1所述的二芳基乙烯有机化合物，其特征在于，通式(1)中R1表示下列结构中的一种：
3.根据权利要求1所述的二芳基乙烯有机化合物，其特征在于，为以下具体化合物中的一种：
4.根据权利要求3所述的二芳基乙烯有机化合物，其特征在于，为化合物1，2或5，结构式如下：
5.一种如权利要求1～4任一项所述的二芳基乙烯有机化合物在制备光致变色材料中的应用。
6.根据权利要求5所述的二芳基乙烯有机化合物在制备光致变色材料中的应用，其特征在于，所述光致变色材料为可见光调控荧光点亮型材料。
7.一种防伪墨水，其特征在于，含有权利要求1～4任一项所述的二芳基乙烯有机化合物。
8.一种如权利要求1～4任一项所述的二芳基乙烯有机化合物的制备方法，其特征在于，包括：
在惰性气氛下，碘代化合物与硼酸化合物用四氢呋喃溶解，再加入Pd(PPh3)4和饱和碳酸钾溶液，将上述反应物的混合溶液于回流条件下，反应12～24h；反应混合物冷却至室温后，乙酸乙酯萃取，合并有机相，无水Na2SO4干燥后旋干；经硅胶柱层析纯化，得到目标产物；
反应式如下：
9.根据权利要求8所述的二芳基乙烯有机化合物的制备方法，其特征在于，所述碘代化合物与硼酸类化合物的摩尔比为1:2.4～2.6，Pd(PPh3)4与硼酸类化合物的摩尔比为0.1:0.9～1.1，饱和碳酸钾溶液与四氢呋喃的体积比为0.5:0.9～1.1。
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