基于聚集诱导荧光的肼二腙类荧光探针和刺激响应材料
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摘要
聚集诱导荧光是一种独特的发光现象，即分子在分散态时具有弱荧光，而在聚集态时则表现出强荧光。与传统荧光染料相比，聚集诱导荧光分子可以有效避免由聚集所引起的荧光淬灭作用。经由水杨醛衍生物和水合肼之间的简单缩合反应得到的二水杨醛缩肼衍生物，正是一类拥有此种独特发光性质的分子。在二水杨醛缩肼结构中，西弗碱与邻位羟基通过分子内氢键形成了稳定的六元环，该结构使整个分子可围绕氮-氮单键自由旋转，由此带来了聚集诱导荧光的发光特征。因此，二水杨醛缩肼衍生物的独特发光行为赋予它在开发新型荧光探针和固体发光材料领域中广阔的应用前景。
鉴于其具有合成简易和发光性能卓越等优势，本文设计了一系列新型具有聚集诱导荧光性质的缩肼类荧光探针和刺激响应材料。首先，本文建立了一种基于聚集诱导荧光机理检测焦磷酸根的分析方法。该方法以二-5-氯水杨醛缩肼为荧光探针，借助铜离子与探针的选择性结合作用构建了一个荧光淬灭的络合体系，该络合体系可用于焦磷酸根的荧光增强型检测，检测限为0.064μM。其次，本文将自由旋转的苯环作为柔性构象因子引入到了二水杨醛缩肼结构中，得到了一种具有聚集诱导荧光和热致荧光变色性质的新型分子-二苯甲酮缩肼。热刺激导致的苯环扭转构象变化是产生热致荧光变色的主要原因：在热退火处理下，苯环发生了较大的扭转构象改变使得分子在晶体中产生更强的分子间相互作用并以更紧密的模式堆积，从而导致其荧光波长变长；在熔融热处理下，分子间的强相互作用被破坏，使得分子在晶体中以较为疏松的模式堆积，从而导致其荧光波长变短。第三，本文将柔性烷基链引入到二苯甲酮缩肼结构中，得到了另外一种基于聚集诱导荧光性质的新型材料-辛烷氧基二苯甲酮缩肼，该材料具有可逆的热致荧光变色以及有机蒸汽致荧光变色功能。研究显示柔性链构象的变化可促使分子在晶体中形成如下三种密堆积模式：近似单体的堆积模式、J-聚集体堆积模式和以二聚体为单元的交叉堆积模式，其在这三种晶体中的荧光波长从534nm到543nm再到558nm，依次发生红移。在热刺激下，晶体由亚稳态的平行堆积模式转为热稳态的交叉堆积模式，导致其荧光波长红移；在有机蒸汽的熏蒸下，二聚体中的π-π相互作用则由于烷基链构象和局部偶极作用的共同变化而被破坏，导致其荧光波长蓝移。
Aggregation-induced emission (AIE) is a unique phenomenon thatAIE-active compounds exhibit weaker fluorescence in solution but strongerfluorescence in the aggregated state. Unlike traditional fluorescent dyes,AIE-active compounds effectively avoid the self-quenching of fluorescenceinduced by aggregation. Salicylaldehyde azine derivatives, facilely prepared bythe condensation between the corresponding salicylaldehydes and hydrazine,displayed such unique AIE property. Induced by the intrameocular hydrogenbond between the Schiff base’s nitrogen and ortho-hydroxyl group, the rigidsix-membered ring in salicylaldehyde azines allowed free rotation of themolecules around N-N single bond, thus leading to their fascinatingaggregation-induced emission property. Therefore, the aforesaid uniqueemission behavior endowed salicylaldehyde azine derivatives with greatpotential in developing new fluorescent probes and solid fluorescent materials.
Given the convenience of preparation and the unique emission behavior,this dissertation was aimed at developing new fluorescent probes and solidfluorescent materials of azines based on the aggregation-induced emission.Firstly, an analytical approach based on AIE mechanism to detectpyrophosphate (PPi) was established with5-chlorosalicylaldehyde azine as theturn-on fluorescent probe. With the aid of selective binding between copper(II)cation and5-chlorosalicylaldehyde azine, a complex system based on AIE wasconstructed and applied in the detection of PPi with the detection limit at0.064μM. Secondly, novel benzophenone azine, exhibiting AIE and thermochromismproperties, was designed and generated by the incorporation of free-rotatingphenyl ring with the conformational flexibility into the scaffold ofsalicylaldehyde azine. Conformational changes of phenyl ring induced bythermal stimuli accounted for the thermochromism. Upon thermal annealingtreatment, the larger conformational rotary of phenyl ring promoted strongerintermolecular interaction and tighter packing mode, and consequently theemission was shifted to longer wavelength. Upon melting treatment, the aforesaid stronger intermolecular interaction was destroyed to release themolecules in the loose packing mode in the crystal structure, and consequentlythe emission was shifted back to shorter wavelength. Thirdly, novel AIEmaterial octanoxyl-substituted benzophenone azine, displaying reversiblethermochromism and vapochromism properties, was designed and produced bythe combination of long alkyl chains with the scaffold of benzophenone azine.Accompanied with the conformational change of the flexible alkyl chain, threedifferent types of packing model, including monomer-like aggregate packingmode, J-aggregate packing mode and the special herringbone packing mode thatcomposed by dimer units, were observed in the crystal structure with theemission red-shifted from534nm to543nm further to558nm. Upon thethermal stimulation, the metastable packing modes of monomer-like aggregateand J-aggregate in the crystal both can be converted to the thermal stableherringbone packing mode, and consequently the emission was red-shifted.Upon exposure to organic vapor, π-π stacking interaction in the dimer units wasdiminished due to the change of alkyl’s conformation and local dipoleinteraction, and thus the emission was blue-shifted.
鉴于其具有合成简易和发光性能卓越等优势，本文设计了一系列新型具有聚集诱导荧光性质的缩肼类荧光探针和刺激响应材料。首先，本文建立了一种基于聚集诱导荧光机理检测焦磷酸根的分析方法。该方法以二-5-氯水杨醛缩肼为荧光探针，借助铜离子与探针的选择性结合作用构建了一个荧光淬灭的络合体系，该络合体系可用于焦磷酸根的荧光增强型检测，检测限为0.064μM。其次，本文将自由旋转的苯环作为柔性构象因子引入到了二水杨醛缩肼结构中，得到了一种具有聚集诱导荧光和热致荧光变色性质的新型分子-二苯甲酮缩肼。热刺激导致的苯环扭转构象变化是产生热致荧光变色的主要原因：在热退火处理下，苯环发生了较大的扭转构象改变使得分子在晶体中产生更强的分子间相互作用并以更紧密的模式堆积，从而导致其荧光波长变长；在熔融热处理下，分子间的强相互作用被破坏，使得分子在晶体中以较为疏松的模式堆积，从而导致其荧光波长变短。第三，本文将柔性烷基链引入到二苯甲酮缩肼结构中，得到了另外一种基于聚集诱导荧光性质的新型材料-辛烷氧基二苯甲酮缩肼，该材料具有可逆的热致荧光变色以及有机蒸汽致荧光变色功能。研究显示柔性链构象的变化可促使分子在晶体中形成如下三种密堆积模式：近似单体的堆积模式、J-聚集体堆积模式和以二聚体为单元的交叉堆积模式，其在这三种晶体中的荧光波长从534nm到543nm再到558nm，依次发生红移。在热刺激下，晶体由亚稳态的平行堆积模式转为热稳态的交叉堆积模式，导致其荧光波长红移；在有机蒸汽的熏蒸下，二聚体中的π-π相互作用则由于烷基链构象和局部偶极作用的共同变化而被破坏，导致其荧光波长蓝移。
Aggregation-induced emission (AIE) is a unique phenomenon thatAIE-active compounds exhibit weaker fluorescence in solution but strongerfluorescence in the aggregated state. Unlike traditional fluorescent dyes,AIE-active compounds effectively avoid the self-quenching of fluorescenceinduced by aggregation. Salicylaldehyde azine derivatives, facilely prepared bythe condensation between the corresponding salicylaldehydes and hydrazine,displayed such unique AIE property. Induced by the intrameocular hydrogenbond between the Schiff base’s nitrogen and ortho-hydroxyl group, the rigidsix-membered ring in salicylaldehyde azines allowed free rotation of themolecules around N-N single bond, thus leading to their fascinatingaggregation-induced emission property. Therefore, the aforesaid uniqueemission behavior endowed salicylaldehyde azine derivatives with greatpotential in developing new fluorescent probes and solid fluorescent materials.
Given the convenience of preparation and the unique emission behavior,this dissertation was aimed at developing new fluorescent probes and solidfluorescent materials of azines based on the aggregation-induced emission.Firstly, an analytical approach based on AIE mechanism to detectpyrophosphate (PPi) was established with5-chlorosalicylaldehyde azine as theturn-on fluorescent probe. With the aid of selective binding between copper(II)cation and5-chlorosalicylaldehyde azine, a complex system based on AIE wasconstructed and applied in the detection of PPi with the detection limit at0.064μM. Secondly, novel benzophenone azine, exhibiting AIE and thermochromismproperties, was designed and generated by the incorporation of free-rotatingphenyl ring with the conformational flexibility into the scaffold ofsalicylaldehyde azine. Conformational changes of phenyl ring induced bythermal stimuli accounted for the thermochromism. Upon thermal annealingtreatment, the larger conformational rotary of phenyl ring promoted strongerintermolecular interaction and tighter packing mode, and consequently theemission was shifted to longer wavelength. Upon melting treatment, the aforesaid stronger intermolecular interaction was destroyed to release themolecules in the loose packing mode in the crystal structure, and consequentlythe emission was shifted back to shorter wavelength. Thirdly, novel AIEmaterial octanoxyl-substituted benzophenone azine, displaying reversiblethermochromism and vapochromism properties, was designed and produced bythe combination of long alkyl chains with the scaffold of benzophenone azine.Accompanied with the conformational change of the flexible alkyl chain, threedifferent types of packing model, including monomer-like aggregate packingmode, J-aggregate packing mode and the special herringbone packing mode thatcomposed by dimer units, were observed in the crystal structure with theemission red-shifted from534nm to543nm further to558nm. Upon thethermal stimulation, the metastable packing modes of monomer-like aggregateand J-aggregate in the crystal both can be converted to the thermal stableherringbone packing mode, and consequently the emission was red-shifted.Upon exposure to organic vapor, π-π stacking interaction in the dimer units wasdiminished due to the change of alkyl’s conformation and local dipoleinteraction, and thus the emission was blue-shifted.
引文
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