点击聚合法制备功能性超支化聚三唑
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摘要
点击聚合是近年来发展起来的一种高效、温和的聚合物合成手段,被广泛应用于各种新型高分子材料的制备。截至目前,已经有大量关于线形聚三唑的文献报道,但关于超支化体系的研究工作还比较少。超支化聚合物具有粘度低、溶解性好、高度支化的三维结构以及有大量可修饰官能团等特点,通常由简单的一步法合成。正因为其独特的结构和突出的性能,超支化聚合物在生物材料、纳米技术等方面具有重要的潜在应用,得到了越来越多的关注。
聚集诱导发光(AIE)是我们课题组观察到的一种特殊的光物理现象：一系列螺旋桨状的分子在溶液态不发光,而聚集后或固态下发射很强的荧光。本文将点击聚合与AIE材料相结合,设计并制备了一系列功能性的超支化聚三唑,并对它们的性能和应用进行了深入研究；同时,利用模型分子,本文对四苯基乙烯(TPE)衍生物具有AIE性能的内在机理进行了探讨和证明。
我们通过独特的弹簧状柔性结构的设计,首次制备了具有AIE性能的超支化聚三唑,从而成功将AIE现象拓展到超支化体系中。该超支化聚三唑具有良好的热稳定性,长烷基链的引入使其拥有很好的成膜性和透光性。外围残留的乙炔和叠氮基团使得聚合物可通过光交联而图案化。另外,聚合物在聚集态下可以检测爆炸物并表现出超放大效应,而且,该荧光探针对2,4,6-三硝基苯酚(PA)的检测灵敏度远大于2,4,6-三硝基甲苯(TNT)。研究发现,检测机理的不同是造成这一现象的原因：对于PA,其主要的荧光猝灭机理是能量转移,而对于TNT则是电荷转移,这是首次对不同爆炸物检测机理的探讨和说明,有助于开发出高灵敏的爆炸物荧光探针。弹簧状柔性结构的设计理念对于新型AIE活性超支化聚合物的制备有着重要的指导意义。
通过分子结构设计,并用常规柱色谱分离手段,我们成功得到了立构纯且具有优异AIE性能的E和Z型TPE衍生物。利用该立体异构体,研究了TPE衍生物的精确AIE机理,结果表明,在荧光测试条件下不能检测到E/Z异构化转变的发生,也就是说,分子内旋转受限(RIR)是TPE基荧光分子具有AIE性能的主要原因。E和Z型异构体的对称和非对称结构对其分子堆积有着重要影响,其中,E型异构体能在特定条件下自组织形成规整有序的微结构,如微纤维、纳米棒等,并表现出光波导性能。得到的两异构体均具有丰富的变色性能,包括机械变色、压致变色、热致变色、时致变色和气致变色等,因具有更规整的结构,E型异构体的变色效应更显著。异构体的多重变色行为与其分子堆积方式在外界刺激下容易发生改变有关,而这则是由AIE材料特有的螺旋桨状结构造成的。
利用设计的A2+B4单体并将其在等浓度下聚合,我们高产率地制备了溶解性能良好、分子量较高且为乙炔基封端的全共轭超支化聚三唑,这是一个无凝胶化的体系且具有很好的重复性。利用外围残留的大量乙炔基团,该聚三唑可以方便地通过点击反应进行表面修饰,例如,用叠氮-炔烃的点击反应,PEG链以一锅法被引入到其外围；而自由基引发的巯基-炔烃的点击反应则将戊硫醇高效地修饰到聚合物表面,且只有一个巯基加成到乙炔基上。超支化聚三唑具有良好的热稳定性,其在800℃时的残炭量最高达74.8%。由于刚性的共轭结构,聚三唑表现出聚集荧光增强(AEE)的性质,且在稀溶液中能形成直径约为100nm的纳米颗粒。该工作开发了一个新颖的可点击荧光平台,利用点击反应可以高效地将各种功能基团或生物分子接到聚合物外围从而赋予其相应的性能和应用。
将TPE和三苯胺(TPA)用三唑环和乙炔基连接,我们分别制备了溶解性和热稳定性均良好的两种共轭超支化聚合物,荧光测试表明,前者表现出聚集荧光猝灭(ACQ)的性质,而后者则是AEE的聚合物。超支化聚三唑的三种模型分子在混合溶剂中均具有AIE的过程,在固态时的荧光均较强,而且,其中一个在特定条件下能得到有趣的发射白光的固体。我们认为该聚三唑的ACQ效应与其中大量的极性三唑基团有关,具体的原因还有待更进一步的研究。
利用AIE活性的超支化聚三唑,我们首次研究了荧光探针在水溶液中检测爆炸物的pH效应。在酸性、中性以及碱性的溶液中,所用的聚合物聚集体均表现出很高的爆炸物检测灵敏度,说明其具有pH耐受性。而且,在酸性THF/buffer混合溶液中,聚集体的荧光猝灭效率得到较显著的提高,说明酸性的环境可以提高爆炸物的检测效率。将聚合物的稀溶液吸附在滤纸上,可制备出爆炸物检测试纸,在pH不同的环境下,该试纸对PA均显示出非常高的检测效率。
Click polymerization, a recently developed effective, mild, and functional group tolerant synthetic method, has now been wildly used in the preparation of various functional polymers. So far, a large number of linear polytriazoles have been prepared, but the research on hyperbranched systems is still rare. Hyperbranched polymers are highly branched macromolecules with some remarkable features, such as one-pot synthesis, low viscosity, high solubility, three dimensional structure and multiple end groups etc. Thanks to their unique structure and outstanding property, hyperbranched polymers could be good candidates in the applications of biomaterial and nano-technology, and thus have drawn growing attention.
Aggregation-induced emission (AIE) is an unusual but interesting photophysical phenomenon observed by our group in2001:a series of propeller-shaped molecules are nonemission when molecularly dissolved but induced to emit intensely by aggregation. In this paper, a series of functional hyperbranched polytriazoles were designed and synthesized through the well combination of click polymerization and AIE materials. Furthermore, the properties and applications of these polymers were investigated in detail. The AIE mechanism of restriction of intramolecular rotation was also proven by study the tetraphenylethene (TPE)-based luminogens.
By taking advantage of the innovative spring-like flexible spacers, we succeeded in synthesizing AIE-active hyperbranched polytriazoles, thus offered the AIE feature to hyperbranched systems. The polymers are soluble and thermally stable, and possess good film-forming ability and satisfactory light transmission. Photopattern could be generated via the photo-crosslinking reaction due to the remaining azide and ethynyl groups on the polymer periphery. Using the novel AIE effect, the polymers could act as chemosensors for the sensitive detection of explosives in their aggregate states with the superamplification quenching effect. The main mechanism for the detection of picric acid (PA) is ascribed to the energy transfer, while that for2,4,6-trinitroroluene (TNT) is the charge transfer. The difference in the quenching mechanism makes the polymer aggregates much more sensitive to PA than TNT. The concept of spring-like polymeric structures is of great value in terms of guiding the further development of hyperbranched polymers with AIE characteristics.
Through rational structure design, we have successfully synthesized a pair of triazole-functionalized TPE derivatives and separated their pure conformers by the commonly used column chromatography technique. Both of the pure E and Z isomers show pronounced AIE effects. Using the precious pure stereoisomers, we have studied the AIE mechanism of TPE-based luminogens and found that no E/Z isomerization could be detected under the conditions of normal PL measurements, thus confirmed that the restriction of intramolecular rotation (RIR) is the main cause. The symmetric and asymmetric shapes of the E and Z isomers significantly affect their molecular packing, and the E isomer could self-organize into ordered microstructures, such as microfibers and nanorods, which exhibit obvious optical waveguiding effect. Both of the conformers undergo multiple chromisms, including mechano-, piezo-, thermo-, chrono-, and vapochromism, and because of its better organizability or crystallinity, the E isomer shows more marked chromic effects. The multiple chromic processes are all associated with changes in the modes of molecular packing which stem from the distinctive structural feature of the A/E luminogens.
Soluble ethynyl-capped hyperbranched conjugated polytriazole with high molecular weight has been firstly constructed in high yield via the polymerization of TPE-containing diyne and tetrazide in equal concentration. This has been proven to be a repeatable and gel-free hyperbranched system. Thanks to the large amount of ethynyl groups on the periphery, this polytriazole could be facilely modified by alkyne-based click reactions. The PEG segment has been introduced onto the polymer via azide-alkyne click reaction in one pot; whereas pentanethiol could be efficiently reacted with the remained ethynyl groups through radical-mediated thiol-yne click reaction, and only one thiol coule be added to an ethynyl group. The obtained polytriazoles are all thermal stable and the char yield at800℃is up to74.8%. Due to the rigid structure, the polymers are aggregation-enhanced emission (AEE) active, and could form unimolecular nanoparticles from their dilute solutions with diameters around100nm. Thus, the polytriazole provides a novel clickable fluorescent platform, onto which various functional groups or biomolecules could be grafted efficiently, which will be surely to find broad applications in biological and optoelectronic fields.
Soluble and thermally stable hyperbranched conjugated polymers containing triphenylamine (TPA) and TPE groups, which are linked by triazoles and triple bonds, respectively, were perepered. The PL measurement indicates that the triazole-linked polymer suffers from an aggregation-caused quenching (ACQ) effect, but the triple-bond linked one is AEE active. Meanwhile, their model compounds are all AIE active regardless the linkage and one of them could form white light emission solid under some special conditions. We thus consider that the ACQ effect of the obtained polytriazole is probably related to the existing large amount of polar triazoles, but the exact cause is still needed to be further investigated.
Using the AIE-active hyperbranched polytriazole, we studied the pH effect on explosive detection in aqueous for the first time. The polymer aggregates are highly sensitive to explosive in acid to basic media, indicating that they are tolerant to various pH conditions. Improved quenching constant has been recorded in the acid THF/buffer mixture, suggesting a simple method to increase the detection efficiency of explosives. The prototype devices (test papers) of the polymer absorbed in filter papers could sense the PA in varying pH solutions. These advantages make the polymer be a good candidate for explosive detection in practical applications.
聚集诱导发光(AIE)是我们课题组观察到的一种特殊的光物理现象：一系列螺旋桨状的分子在溶液态不发光,而聚集后或固态下发射很强的荧光。本文将点击聚合与AIE材料相结合,设计并制备了一系列功能性的超支化聚三唑,并对它们的性能和应用进行了深入研究；同时,利用模型分子,本文对四苯基乙烯(TPE)衍生物具有AIE性能的内在机理进行了探讨和证明。
我们通过独特的弹簧状柔性结构的设计,首次制备了具有AIE性能的超支化聚三唑,从而成功将AIE现象拓展到超支化体系中。该超支化聚三唑具有良好的热稳定性,长烷基链的引入使其拥有很好的成膜性和透光性。外围残留的乙炔和叠氮基团使得聚合物可通过光交联而图案化。另外,聚合物在聚集态下可以检测爆炸物并表现出超放大效应,而且,该荧光探针对2,4,6-三硝基苯酚(PA)的检测灵敏度远大于2,4,6-三硝基甲苯(TNT)。研究发现,检测机理的不同是造成这一现象的原因：对于PA,其主要的荧光猝灭机理是能量转移,而对于TNT则是电荷转移,这是首次对不同爆炸物检测机理的探讨和说明,有助于开发出高灵敏的爆炸物荧光探针。弹簧状柔性结构的设计理念对于新型AIE活性超支化聚合物的制备有着重要的指导意义。
通过分子结构设计,并用常规柱色谱分离手段,我们成功得到了立构纯且具有优异AIE性能的E和Z型TPE衍生物。利用该立体异构体,研究了TPE衍生物的精确AIE机理,结果表明,在荧光测试条件下不能检测到E/Z异构化转变的发生,也就是说,分子内旋转受限(RIR)是TPE基荧光分子具有AIE性能的主要原因。E和Z型异构体的对称和非对称结构对其分子堆积有着重要影响,其中,E型异构体能在特定条件下自组织形成规整有序的微结构,如微纤维、纳米棒等,并表现出光波导性能。得到的两异构体均具有丰富的变色性能,包括机械变色、压致变色、热致变色、时致变色和气致变色等,因具有更规整的结构,E型异构体的变色效应更显著。异构体的多重变色行为与其分子堆积方式在外界刺激下容易发生改变有关,而这则是由AIE材料特有的螺旋桨状结构造成的。
利用设计的A2+B4单体并将其在等浓度下聚合,我们高产率地制备了溶解性能良好、分子量较高且为乙炔基封端的全共轭超支化聚三唑,这是一个无凝胶化的体系且具有很好的重复性。利用外围残留的大量乙炔基团,该聚三唑可以方便地通过点击反应进行表面修饰,例如,用叠氮-炔烃的点击反应,PEG链以一锅法被引入到其外围；而自由基引发的巯基-炔烃的点击反应则将戊硫醇高效地修饰到聚合物表面,且只有一个巯基加成到乙炔基上。超支化聚三唑具有良好的热稳定性,其在800℃时的残炭量最高达74.8%。由于刚性的共轭结构,聚三唑表现出聚集荧光增强(AEE)的性质,且在稀溶液中能形成直径约为100nm的纳米颗粒。该工作开发了一个新颖的可点击荧光平台,利用点击反应可以高效地将各种功能基团或生物分子接到聚合物外围从而赋予其相应的性能和应用。
将TPE和三苯胺(TPA)用三唑环和乙炔基连接,我们分别制备了溶解性和热稳定性均良好的两种共轭超支化聚合物,荧光测试表明,前者表现出聚集荧光猝灭(ACQ)的性质,而后者则是AEE的聚合物。超支化聚三唑的三种模型分子在混合溶剂中均具有AIE的过程,在固态时的荧光均较强,而且,其中一个在特定条件下能得到有趣的发射白光的固体。我们认为该聚三唑的ACQ效应与其中大量的极性三唑基团有关,具体的原因还有待更进一步的研究。
利用AIE活性的超支化聚三唑,我们首次研究了荧光探针在水溶液中检测爆炸物的pH效应。在酸性、中性以及碱性的溶液中,所用的聚合物聚集体均表现出很高的爆炸物检测灵敏度,说明其具有pH耐受性。而且,在酸性THF/buffer混合溶液中,聚集体的荧光猝灭效率得到较显著的提高,说明酸性的环境可以提高爆炸物的检测效率。将聚合物的稀溶液吸附在滤纸上,可制备出爆炸物检测试纸,在pH不同的环境下,该试纸对PA均显示出非常高的检测效率。
Click polymerization, a recently developed effective, mild, and functional group tolerant synthetic method, has now been wildly used in the preparation of various functional polymers. So far, a large number of linear polytriazoles have been prepared, but the research on hyperbranched systems is still rare. Hyperbranched polymers are highly branched macromolecules with some remarkable features, such as one-pot synthesis, low viscosity, high solubility, three dimensional structure and multiple end groups etc. Thanks to their unique structure and outstanding property, hyperbranched polymers could be good candidates in the applications of biomaterial and nano-technology, and thus have drawn growing attention.
Aggregation-induced emission (AIE) is an unusual but interesting photophysical phenomenon observed by our group in2001:a series of propeller-shaped molecules are nonemission when molecularly dissolved but induced to emit intensely by aggregation. In this paper, a series of functional hyperbranched polytriazoles were designed and synthesized through the well combination of click polymerization and AIE materials. Furthermore, the properties and applications of these polymers were investigated in detail. The AIE mechanism of restriction of intramolecular rotation was also proven by study the tetraphenylethene (TPE)-based luminogens.
By taking advantage of the innovative spring-like flexible spacers, we succeeded in synthesizing AIE-active hyperbranched polytriazoles, thus offered the AIE feature to hyperbranched systems. The polymers are soluble and thermally stable, and possess good film-forming ability and satisfactory light transmission. Photopattern could be generated via the photo-crosslinking reaction due to the remaining azide and ethynyl groups on the polymer periphery. Using the novel AIE effect, the polymers could act as chemosensors for the sensitive detection of explosives in their aggregate states with the superamplification quenching effect. The main mechanism for the detection of picric acid (PA) is ascribed to the energy transfer, while that for2,4,6-trinitroroluene (TNT) is the charge transfer. The difference in the quenching mechanism makes the polymer aggregates much more sensitive to PA than TNT. The concept of spring-like polymeric structures is of great value in terms of guiding the further development of hyperbranched polymers with AIE characteristics.
Through rational structure design, we have successfully synthesized a pair of triazole-functionalized TPE derivatives and separated their pure conformers by the commonly used column chromatography technique. Both of the pure E and Z isomers show pronounced AIE effects. Using the precious pure stereoisomers, we have studied the AIE mechanism of TPE-based luminogens and found that no E/Z isomerization could be detected under the conditions of normal PL measurements, thus confirmed that the restriction of intramolecular rotation (RIR) is the main cause. The symmetric and asymmetric shapes of the E and Z isomers significantly affect their molecular packing, and the E isomer could self-organize into ordered microstructures, such as microfibers and nanorods, which exhibit obvious optical waveguiding effect. Both of the conformers undergo multiple chromisms, including mechano-, piezo-, thermo-, chrono-, and vapochromism, and because of its better organizability or crystallinity, the E isomer shows more marked chromic effects. The multiple chromic processes are all associated with changes in the modes of molecular packing which stem from the distinctive structural feature of the A/E luminogens.
Soluble ethynyl-capped hyperbranched conjugated polytriazole with high molecular weight has been firstly constructed in high yield via the polymerization of TPE-containing diyne and tetrazide in equal concentration. This has been proven to be a repeatable and gel-free hyperbranched system. Thanks to the large amount of ethynyl groups on the periphery, this polytriazole could be facilely modified by alkyne-based click reactions. The PEG segment has been introduced onto the polymer via azide-alkyne click reaction in one pot; whereas pentanethiol could be efficiently reacted with the remained ethynyl groups through radical-mediated thiol-yne click reaction, and only one thiol coule be added to an ethynyl group. The obtained polytriazoles are all thermal stable and the char yield at800℃is up to74.8%. Due to the rigid structure, the polymers are aggregation-enhanced emission (AEE) active, and could form unimolecular nanoparticles from their dilute solutions with diameters around100nm. Thus, the polytriazole provides a novel clickable fluorescent platform, onto which various functional groups or biomolecules could be grafted efficiently, which will be surely to find broad applications in biological and optoelectronic fields.
Soluble and thermally stable hyperbranched conjugated polymers containing triphenylamine (TPA) and TPE groups, which are linked by triazoles and triple bonds, respectively, were perepered. The PL measurement indicates that the triazole-linked polymer suffers from an aggregation-caused quenching (ACQ) effect, but the triple-bond linked one is AEE active. Meanwhile, their model compounds are all AIE active regardless the linkage and one of them could form white light emission solid under some special conditions. We thus consider that the ACQ effect of the obtained polytriazole is probably related to the existing large amount of polar triazoles, but the exact cause is still needed to be further investigated.
Using the AIE-active hyperbranched polytriazole, we studied the pH effect on explosive detection in aqueous for the first time. The polymer aggregates are highly sensitive to explosive in acid to basic media, indicating that they are tolerant to various pH conditions. Improved quenching constant has been recorded in the acid THF/buffer mixture, suggesting a simple method to increase the detection efficiency of explosives. The prototype devices (test papers) of the polymer absorbed in filter papers could sense the PA in varying pH solutions. These advantages make the polymer be a good candidate for explosive detection in practical applications.
引文
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