CN114163595B - 一种基于二维共价有机框架的热激活延迟荧光探针材料 - Google Patents
一种基于二维共价有机框架的热激活延迟荧光探针材料 Download PDFInfo
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Abstract
本发明公开一种基于二维共价有机框架的热激活延迟荧光探针材料,合成一类基于三嗪并以C=N键连接的能够特定识别金属离子的探针分子。这类分子由于含有多个苯环,刚性离域大π键结构的使其具有本征的发光的属性。COFs较大的孔道尺寸可以为特殊金属离子的引入提供空间需求,从而形成多功能复合探针材料。
Description
技术领域
本发明具体涉及一种基于二维共价有机框的热激活延迟架荧光材料的制备方法及其应用,属于化合物技术领域。
背景技术
共价有机框架材料是一种具有周期性结构的晶态多孔有机材料。有机构建单元通过共价键实现了原子级别精确连接进而形成了具有周期性排列的多孔框架材料。由于共价有机框架材料通过轻元素通过强共价键连接,因此它具有较低的密度,高的热稳定性和固有的孔隙率。根据建筑单元的不同尺寸,我们可以将共价有机框架材料分为二维和三维共价有机框架材料。在二维共价有机框架材料中,固定点和边缘通过共价键连接以形成延伸的二维多边形层,这些层通过堆叠层形成多层框架,从而产生周期性的π阵列和有序的一维孔道,因此有着良好的共轭π-π层堆积而展现出高效的电子流动性,能够有效的提升电荷的分离和转移。
热激活延迟荧光材料在单重态和三重态具有较小能极差时,通常反向系间窜越(RISC)实现三重态到单重态的能量转换,具有理论上100%的激子利用率。TADF材料分子设计中,电子给体主要是具有较强的给电子能力、较高的T1态能级、较好的稳定性等特点的芳胺结构单元,如咔唑、吖啶、叔丁基咔唑、三苯胺、吩噁嗪及二氢吩嗪等;而电子受体主要为含氮杂环,如三嗪、氰基苯、二苯砜、苯并内酰亚胺及萘酰亚胺等。
基于上述TADF材料具有良好的荧光量子效率,较长的荧光寿命,在有机荧光探针的设计中,常常引入此类分子或者固定的官能团对离子进行识别,如醛基和席夫碱类。此外,引入扭曲构象或饱和体系可以保持TADF材料具有较高的三重态能量,从而避免能量泄漏;引入提供孤对电子的N或者S原子,具有的分子,nπ*的三重态能够提高反向系间窜越速率。
发明内容
本发明的目的在于提出一种基于二维共价有机框架的热激活延迟荧光探针材料,合成一类基于三嗪并以C=N键连接的能够特定识别金属离子的探针分子。这类分子由于含有多个苯环,刚性离域大π键结构的使其具有本征的发光的属性。COFs较大的孔道尺寸可以为特殊金属离子的引入提供空间需求,从而形成多功能复合探针材料。
为了实现上述目的,本发明采用的技术方案如下:
该材料具体是一种热激活延迟荧光多孔聚合物材料,具有以下具体合成通式:
通式
上述合成通式中,代表醛基作为活性位的树枝状连接单元,其分子核心包含-三嗪电子受体,咔唑或三苯胺类电子给体,电子给受体结合构成发光单元,/>代表氨基作为活性位的树枝状连接单元。
通式的为树枝状醛基类,其中n代表烷基链中碳原子的个数,且不小于2,结构如下:
通式中的为芳香类四胺,其中,n代表苯环的个数,且不小于2,结构如下:
这种材料具有无重金属的参与、可达到100%的理论内量子效率、合成条件简单温和、产品收率和纯度较高等一系列优点,是一种具有广阔的应用前景、可大规模投产的商用多功能材料。
优选地,上述的热激活延迟荧光材料为具有如下结构的化合物:
C1
或
C2
上述技术方案可以得到以下有益效果:
二维共价有机框架材料是一种长程且具有序周期阵列结构的晶体框架材料,其结构是可以根据拓扑结构进行预先设计。通过设计具有不同形状,尺寸和连接组的构件块,可以获得具有不同形状和尺寸的一维通道。
由于有机框架材料属于多孔聚合物,单一或数个特定组合的C=N官能团对金属离子有螯合作用,从而通过抑制分子内电荷转移使得荧光减弱或者猝灭,因此可对不同浓度的特定金属离子进行荧光识别。
较长的烷基链改善了整体分子的柔性,使得材料具有更好的溶解性,同时因为碳链的扭转加速了金属离子的进入,促进了螯合作用。
具体实施方式
下面结合实施例对本发明做进一步的说明:
该材料具体是一种热激活延迟荧光多孔聚合物材料,具有以下具体合成通式:
通式
上述合成通式中,代表醛基作为活性位的树枝状连接单元,其分子核心包含-三嗪电子受体,咔唑或三苯胺类电子给体,电子给受体结合构成发光单元,/>代表氨基作为活性位的树枝状连接单元。
通式的为树枝状醛基类,其中n代表烷基链中碳原子的个数,且不小于2,结构如下:
通式中的为芳香类四胺,其中,n代表苯环的个数,且不小于2,结构如下:
这种材料具有无重金属的参与、可达到100%的理论内量子效率、合成条件简单温和、产品收率和纯度较高等一系列优点,是一种具有广阔的应用前景、可大规模投产的商用多功能材料。
优选地,上述的热激活延迟荧光材料为具有如下结构的化合物:
C1
或
C2
实施例1
n为2时,合成C1。将三嗪吩恶嗪醛(0.5g,0.63mmol)与四吡咯苯胺(1g,5.1mmol)加入到含有40mL乙醇的三颈烧瓶中,继续缓慢加入5mL1,4-二氧六环和0.5mL的乙酸水溶液,在80℃下搅拌反应24h。反应过后将溶液冷却至室温,加入适量去离子水析出反应产物,析出产物继续用乙醇洗涤,并在真空下干燥以得到淡黄色固体。
实施例2
n为2时,合成C2。将三嗪三苯胺醛(0.5g,0.51mmol)与四吡咯苯胺(1g,5.1mmol)加入到含有40mL乙醇的三颈烧瓶中,继续缓慢加入5mL1,4-二氧六环和0.5mL的乙酸水溶液,在80℃下搅拌反应24h。反应过后将溶液冷却至室温,加入适量去离子水析出反应产物,析出产物继续用乙醇洗涤,并在真空下干燥以得到淡黄色固体。
以上所述均为本发明的优选实施方式,对于本技术领域的普通技术人员,在不脱离本发明的原理前提下,对本发明的各种等价形式的修改均属于本申请所附权利要求的保护范围。
Claims (4)
1.一种基于二维共价有机框架的热激活延迟荧光探针材料,其特征在于:具有以下具体合成通式:
通式
上述合成通式中,代表醛基作为活性位的树枝状连接单元,其分子核心包含-三嗪电子受体,咔唑或三苯胺类电子给体,电子给受体结合构成发光单元,/>代表氨基作为活性位的树枝状连接单元。
2.根据权利要求1所述的一种基于二维共价有机框架的热激活延迟荧光探针材料,其特征在于:通式的为树枝状醛基类,其中n代表烷基链中碳原子的个数,且不小于2,结构如以下其中一种:
3.根据权利要求1所述的一种基于二维共价有机框架的热激活延迟荧光探针材料,其特征在于:通式中的为芳香类四胺,其中,n代表苯环的个数,且不小于2,结构如以下其中一种:
4.根据权利要求1所述的一种基于二维共价有机框架的热激活延迟荧光探针材料,其特征在于:热激活延迟荧光材料为具有如下结构的化合物:
C1
或
C2
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CN112898515A (zh) * | 2021-01-23 | 2021-06-04 | 西安科技大学 | 具有三嗪结构的多孔共价有机框架材料的制备方法 |
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