CN112079950B - 热活化延迟荧光温敏聚合物及其制备方法 - Google Patents
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Abstract
热活化延迟荧光温敏聚合物及其制备方法属于温度传感材料技术领域。现有荧光温敏聚合物中的荧光小分子化合物的激发态寿命短。本发明之热活化延迟荧光温敏聚合物具有TADF效应,其荧光寿命延长到0.71~3.43微秒,因而,克服了现有荧光温敏聚合物荧光寿命只有1~100纳秒之不足,而背景荧光的荧光寿命也在纳秒量级,因此,本发明能够避免背景荧光干扰,提高温敏检测灵敏度。同时,本发明之热活化延迟荧光温敏聚合物制备方法采用有机催化剂替代现有技术中的金属催化剂催化基团转移聚合,避免了金属杂质残留带来的问题,也就是所制备的产物用作发光材料具有正常的使用寿命。
Description
技术领域
本发明涉及一种热活化延迟荧光温敏聚合物及其制备方法,属于温度传感材料技术领域。
背景技术
温度是一个重要的环境变量,对温度的原位监测无论在科学研究还是实际应用中都具有重要意义。常用的温度监测仪器是基于某一温度依赖的物理性质设计,例如电导、电阻或体积等。温度原位监测技术因其对被测体系干扰小、能够实时反应现场温度等特点,在分析诊断、工业生产、国防军工等领域表现出越来越明显的优势,并衍生出红外、液晶等诸多温度原位监测技术和测温设备。荧光温敏聚合物是一种荧光强度或者波长随温度变化而变化的功能性材料,具有响应速度快、灵敏度高、空间分辨率高、可视化等优点,应用于生物检测、温度传感等领域,例如,适用于一些微环境及生物体等,作为荧光温度探针分子和传感材料。
但是,现有荧光温敏聚合物其结构特征是普通荧光小分子化合物与具有温敏特性的聚合物(如聚N-异丙基丙烯酰胺)通过化学键而接枝,其缺点在于,普通荧光小分子化合物的激发态寿命较短,也就是荧光寿命通常在纳秒量级,因而,易于受到纳秒量级短荧光寿命背景光的干扰,使其荧光传感的灵敏度降低。另外,虽然在现有技术中出现了一种具有热活化延迟荧光效应(TADF)的聚合物,因热活化其荧光寿命得以延迟,但是,该聚合物只是一种荧光发光材料,不具有足以使其成为温敏材料的温敏性,并且,其制备方法使用金属催化剂,存在金属杂质残留问题,导致发光材料寿命缩短。
发明内容
为了延长荧光温敏聚合物中的普通荧光小分子化合物的激发态寿命,以避免背景光的干扰,提高荧光温敏聚合物温度传感灵敏度,我们发明了一种热活化延迟荧光温敏聚合物及其制备方法。
本发明之热活化延迟荧光温敏聚合物是一种有机高分子聚合物,其特征在于,其结构式为:
式中:
x为2~9999之间的整数,y为1~20之间的整数,m为0或者1,n为1、2、3或者4;
X选自-C(R'R")-、-Si(R'R")-、-N(R')-、-O-、-S-、-SO-、-SO2-、-B(R')-、-P(R')-和-PO(R')-中的一种或者多种;
所述R、R'、R"选自H、卤素、-CF3、-CN、-NO2、取代或者非取代的C1~C20的烷基、取代或者非取代的C1~C20的烷氧基、取代或者非取代的C3~C20的环烷基、取代或者非取代的C5~C20的杂环烷基、取代或者非取代的C6~C20的芳基和取代或者非取代的C2~C20的杂芳基中的一种或者多种。
本发明之热活化延迟荧光温敏聚合物制备方法其特征在于:
首先,在氮气或者惰性气体提供的保护气氛中,将丙烯酸正丁酯单体、1-甲氧基-1-三异丙基硅基-2-甲基-1-丙烯引发剂、N-(三甲基硅基)二(三氟甲磺酰基)-胺有机催化剂溶解于甲苯并混合,所述单体其结构式为:
所述引发剂的用量为所述单体摩尔量的2%~6%,所述催化剂的用量为所述单体摩尔量的0.001%~1%,反应后加入FT-Br终止剂,继续反应后得到端基含-Br的基团转移聚合物,其结构式为:
其次,氮气或者惰性气体提供的保护气氛中,将所述端基含-Br的基团转移聚合物与含有酚羟基的热活化延迟荧光单元、Cs2CO3溶解于N,N-二甲基甲酰胺溶剂并混合,所述荧光单元其结构式为:
反应后得到热活化延迟荧光温敏聚合物产物,所述产物其结构式为:
本发明之热活化延迟荧光温敏聚合物具有TADF效应,与现有技术相比,其荧光寿命延长到0.71~3.43微秒,因而,克服了现有荧光温敏聚合物荧光寿命只有1~100纳秒之不足,而背景荧光的荧光寿命也在纳秒量级,因此,本发明能够避免背景荧光干扰,提高温敏检测灵敏度。
本发明的两个实施例获得的产物,其荧光强度与时间、温度关系曲线表明,如图1所示,当采用本发明之热活化延迟荧光温敏聚合物,利用其荧光强度与温度关系监测温度时,即使在延迟时间为2微秒时,产物的荧光强度在50~300K的温度区间内仍保持荧光强度与温度的严格关系,即随温度的升高,荧光强度对应升高,因此,在此温度区间内根据荧光强度即可可以得知被测物的温度。
同时,本发明之热活化延迟荧光温敏聚合物制备方法采用有机催化剂替代现有技术中的金属催化剂催化基团转移聚合,避免了金属杂质残留带来的问题,也就是所制备的产物用作发光材料具有正常的使用寿命。
附图说明
图1为本专利申请所举例子制备的热活化延迟荧光温敏聚合物的荧光强度与时间、温度关系曲线图,图1同时作为摘要附图。
具体实施方式
有关本发明之热活化延迟荧光温敏聚合物的具体内容如下所述。
式中:R1选自取代或者未取代的C1~C20的烷基、取代或者未取代的C3~C20的环烷基、取代或者未取代的C5~C20的杂环烷基和取代或者未取代的C6~C20的芳基中的一种或者多种。
至此,本发明之热活化延迟荧光温敏聚合物的具体结构能够为至少以下10种中的任意一种:
下面举例说明本发明。
本发明之热活化延迟荧光温敏聚合物的制备路线如下:
首先,制备端基含-Br的基团转移聚合物:
在氩气保护气氛中,将160mg、1.25mmol的丙烯酸正丁酯单体与12.9mg、50μmol的1-甲氧基-1-三异丙基硅基-2-甲基-1-丙烯引发剂溶解于2.5mL甲苯中,加入2.5μmol的N-(三甲基硅基)二(三氟甲磺酰基)-胺有机催化剂(Me3SiNTf2);反应3分钟后,加入38.3mg、150μmol的FT-Br终止剂,继续反应20小时;反应结束后,向反应体系中加入10μL的甲醇淬灭反应,将产物在丙酮中透析,得到端基含-Br的基团转移聚合物;对所得端基含-Br的基团转移聚合物的分子量进行表征,其数均分子量为42.7kDa,重均分子量为51.2kDa,分散度(PDI)为1.20。
其次,热活化延迟荧光温敏聚合物产物的制备:
在氩气保护气氛中,将所述端基含-Br的基团转移聚合物与148mg、200μmol的含有酚羟基的热活化延迟荧光单元,130mg、400μmol的Cs2CO3溶解于10mL的N,N-二甲基甲酰胺溶剂并混合,在60℃下反应8小时;反应结束后降至室温,将反应液倒入水中,用二氯甲烷萃取,用无水硫酸钠使出现的有机层干燥,旋干溶剂后得到的固体经柱层析分离,以二氯甲烷为洗脱剂,得到热活化延迟荧光温敏聚合物产物;对所得热活化延迟荧光温敏聚合物产物的分子量进行表征,其数均分子量为42.1kDa,重均分子量为50.5kDa,分散度(PDI)为1.20。所述热活化延迟荧光温敏聚合物产物的荧光强度与时间、温度关系如图1所示。
Claims (8)
1.一种热活化延迟荧光温敏聚合物,其特征在于,其结构式为:
式中:
x为2~9999之间的整数,y为1~20之间的整数,m为0或者1,n为1、2、3或者4;
X选自-C(R'R")-、-Si(R'R")-、-N(R')-、-O-、-S-、-SO-、-SO2-、-B(R')-、-P(R')-和-PO(R')-中的一种或者多种;
所述R、R'、R"选自H、卤素、-CN、-NO2、取代或者非取代的C1~C20的烷基、取代或者非取代的C1~C20的烷氧基、取代或者非取代的C3~C20的环烷基、取代或者非取代的C5~C20的杂环烷基、取代或者非取代的C6~C20的芳基和取代或者非取代的C2~C20的杂芳基中的一种或者多种。
8.一种热活化延迟荧光温敏聚合物制备方法,其特征在于:
首先,在氮气或者惰性气体提供的保护气氛中,将丙烯酸正丁酯单体、1-甲氧基-1-三异丙基硅基-2-甲基-1-丙烯引发剂、N-(三甲基硅基)二(三氟甲磺酰基)-亚胺有机催化剂溶解于甲苯并混合,所述单体其结构式为:
所述引发剂的用量为所述单体摩尔量的2%~6%,所述催化剂的用量为所述单体摩尔量的0.001%~1%,反应后加入FT-Br终止剂,继续反应后得到端基含-Br的基团转移聚合物,其结构式为:
其次,氮气或者惰性气体提供的保护气氛中,将所述端基含-Br的基团转移聚合物与含有酚羟基的热活化延迟荧光单元、Cs2CO3溶解于N,N-二甲基甲酰胺溶剂并混合,所述荧光单元其结构式为:
反应后得到热活化延迟荧光温敏聚合物产物,所述产物其结构式为:
式中:
x为2~9999之间的整数,y为1~20之间的整数,m为0或者1,n为1、2、3或者4;
X选自-C(R'R")-、-Si(R'R")-、-N(R')-、-O-、-S-、-SO-、-SO2-、-B(R')-、-P(R')-和-PO(R')-中的一种或者多种;
所述R、R'、R"选自H、卤素、-CN、-NO2、取代或者非取代的C1~C20的烷基、取代或者非取代的C1~C20的烷氧基、取代或者非取代的C3~C20的环烷基、取代或者非取代的C5~C20的杂环烷基、取代或者非取代的C6~C20的芳基和取代或者非取代的C2~C20的杂芳基中的一种或者多种。
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