固态发光可调的新型聚集诱导发光材料的合成、晶体结构及光物理性质
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摘要
作为显示、照明等有机发光器件中的关键组成部分,有机发光材料的性能很大程度上决定了发光器件的发展及其实用化进程。有机发光材料往往以固态薄膜的形式出现在发光器件中,所以研究和探索高效固态发光的有机材料具有重大意义。聚集诱导发光现象为开发强发光的有机材料提供了一个有效方法,并在过去十年发展了大量基于噻咯、四苯乙烯和苯乙烯腈等单元结构的聚集诱导发光材料。
利用化学和/或物理方法调控有机材料固态下的发光行为及其产生机制受到了越来越广泛的重视。压致荧光变色材料是一类新型的力刺激响应智能材料,它在信息存储、商标防伪和微应力传感等领域具有潜在的应用,但是具有压致荧光变色性能的有机化合物目前尚十分稀少。本论文主要致力于开发新核结构的聚集诱导发光材料,并通过化学修饰或外部刺激的方法实现固态发光行为的调控,其主要内容概括如下：
第一章重点介绍了激发态分子的光物理过程,并对高效固态发光的有机小分子材料及荧光调控的最新进展进行了综述。
第二章基于对1,1,4,4-四苯基丁二烯结构的修饰,设计合成了四种多取代2,2'-联二茚发光团1a、2a、3a和4a,并充分研究了它们在溶液和固态下的光物理性质。化合物1a-4a在溶液中发光微弱,但是在晶体下发光很强,表现出聚集诱导发光性质。通过缓慢溶剂挥发法,成功获得了化合物1a-4a的单晶。通过单晶结构分析,发现分子在晶体中具有十分扭曲的构型,不存在分子间的p-p堆积作用,导致形成了非紧密堆积结构,这是高效发光的重要原因。化合物1a-3a的晶体发射深蓝色荧光,4a的晶体为绿色；而化合物1a-3a的无定形薄膜红移到天蓝色,4a的无定形薄膜仍为绿色。这表明化合物1a-3a的固态发光依赖于它们的分子构型及堆积状态。进一步研究了化合物1a-3a压致荧光变色性能,并通过粉末X-射线衍射(PXRD)和差式扫描量热法(DSC)的测试验证压致变色的机制。
第三章在上一章的基础上,为了将2,2'-联二茚体系的发光向长波长方向拓展同时获得高效固态发光的BODIPY类荧光团,创新性地将BODIPY基团引入到多取代2,2’-联二茚体系中,设计合成了化合物BDY-IN.化合物BDY-IN仍具有聚集诱导发光性质。利用再沉淀法得到了化合物BDY-IN两种发光差异很大的纳米聚集体,最大发射分别为543nm和646nm,这表明BDY-IN的聚集态发光受聚集形式影响。采用缓慢溶剂挥发法,通过氯仿/乙醇体系中培养出发橙色荧光的单晶BDY-O,最大发射为582nm；通过二氯甲烷/乙醇体系中培养出发红色荧光的单晶BDY-R,最大发射为分别661nm。通过对两种单晶结构的分析发现,BDY-R的分子构型比BDY-O的更为平整且BDY-R的晶体中存在分子间p-p堆积作用,这两个原因导致了BDY-R比BDY-O发光红移约79nm。
第四章设计合成了三种含有三苯乙烯腈和三苯胺基元的化合物CN-TPA、3CN-TPA和4CN-DTPA。研究了三种化合物的聚集诱导发光特性,同时发现了化合物CN-TPA的固体粉末具有压致荧光变色效应。化合物CN-TPA的晶体粉末发蓝绿色荧光(594nm),碾磨可以将其破坏成发黄绿色荧光(545nm)的无定形粉末,再经加热可以恢复成发蓝绿色荧光(594nm)的晶体粉末。粉末X-射线衍射(PXRD)表明化合物CN-TPA的晶体和无定形粉末具有不同的分子堆积模式。差式扫描量热法(DSC)测试显示,晶体是热力学稳定态,而无定形态是亚稳态。采用缓慢溶剂挥发法,获得了化合物CN-TPA发蓝绿色荧光(584nm)的单晶。通过单晶结构分析,发现在晶体中分子构型十分扭曲,导致了形成了非紧密堆积结构；这样,外部压力可以容易地破坏分子构型及堆积模式,从而引起相变。
第五章利用一步生成两根C-N键成环的方法合成了系列稠环取代的N,N’-二芳基吩嗪衍生物(M1-flu、M2-py和M3-phen)。发现该类化合物在溶液中表现出不依赖于溶剂极性的高达240nm的Stocks位移。它们的溶液最大发射在600nm左右,而固体粉末在蓝、绿光区域。以化合物M1-flu作为发光材料初步研究了该类化合物的电致发光性质。
第六章设计合成了茚修饰的9,10-二苯基蒽衍生物INAN,并与参比化合物9,10-二(4-(2,2-二苯乙烯基)苯)蒽DPAV比较,初步研究了其光物理性能。
第七章结论。
As a key component in the organic light-emitting devices (OLEDs), the organic light-emitting materials largely affect the process of industrialization of OLEDs. The organic light-emitting materials are practically used as thin films in OLEDs, so it is of great significance to study and explore organic materials with highly efficient solid state emission. Aggregation-induced emission phenomenon (AIE) offers an effective approach for the development of highly luminous organic materials, and in the past decade a large number of AIE-active dyes based on the core-structure with silole or tetraphenylethene have been developed.
The switching and tuning of organic solid-state fluorescence via chemical and/or physical methods and its mechanism is of great current interest. Mechanochromic fluorescent materials are a class of smart materials with fluorescent properties that change in response to external force stimuli, which could be used in memory chips, sensors, and security inks. However, organic mechanochromic fluorescent materials that are dependent on changes in physical molecular packing modes are extremely rare. This thesis mainly contributes to develop novel core-structures AIE fluorophores, and switch and tune these dyes' solid-state emission through chemical modification or external stimuli. Its main contents summarized as follows.
In chapter one, the photophysical processes of excited molecules are briefly introduced. The latest progress of organic small molecules with highly efficient solid-state emission and various strategies that have been effectively utilized to achieve switchable and tunable fluorescence in the organic solid state are reviewed.
In chapter two, based on the structure of1,1,4,4-tetraphenyl butadiene, four polysubstituted2,2'-biindenyl fluorophores la,2a,3a and4a were designed and synthesized, and their optical properties in solution and solid-state were investigated. Compounds la-4a have the AIE nature. Single crystals of these dyes were obtained by slow solvent evaporation method. The large interplane angles in the cystals make the conformations of la-4a largely deviated from a planar conformation, which prevents molecules from p-p stacking interactions, and thus induces intense emissions in crystal state. The crystals of la-3a show intense blue luminescence, and4a green; while the amorphous film's emission of la-3a red-shift to sky blue, and4a still green. This suggests that solid state emission of compounds la-3a depends on their molecular conformation and packing mode. The mechanochromic ability of la-3a was further examined, and the powder X-ray diffraction (XRD) and differential scanning calorimetry (DSC) measurements were carried out to validate the mechanism of mechanochromism.
In chapter three, based on the last chapter, in order to expand the emission of2,2'-biindenyl derivatives to red region and obtain the BODIPY fluorophore with highly efficient solid state emission, BODIPY moieties were innovatively incorporated into2,2'-biindenyl systems. Bodipy fluorophore BDY-IN was designed and synthesized. BDY-IN still has the AIE nature. Two kinds nano-particles of BDY-IN were prepared by reprecipitation, and they exhibited distinct emission which suggested that the emission of the nano-particles depends on BDY-IN molecular packing mode in the aggregate. The BDY-IN crystals with two polymorphic forms (BDY-O and BDY-R) have been obtained. Due to the more planar conformation and face to face p-p stacking interaction increasing the p-conjugated degree, the emission of BDY-R displays an obvious red shift about79nm compared with BDY-O.
In chapter four, three fluorophores (CN-TPA,3CN-TPA and4CN-DTPA) containing triphenylacrylonitrile and triphenylamines moieties were designed and synthesized. These three dyes are all AIE-active, and CN-TPA display mechanochromism in solid phase. Grinding could disrupt the crystalline CN-TPA with blue-green emission into amorphous CN-TPA with yellow-green emission, and heating treatment could change the amorphous CN-TPA into crystalline CN-TPA. Powder X-ray diffraction (PXRD) characterizations demonstrated that crystalline and amorphous CN-TPA possesses different molecular packing. A differential scanning calorimetry (DSC) measurement revealed that the emission switching was due to the exchange between the thermodynamic-stable crystalline and metastable amorphous states. Single crystals of CN-TPA were gotten by slow solvent evaporation method. The reason for the phase transformation caused by external pressure is ascribed to the twisted conformation of the molecule which leads to poor solid molecular packing and weak interactions in the interfaces of lamellar layers confirmed by its single-crystal X-ray diffraction analysis.
In chapter five, the fused ring substituted N,N-diaryl phenazine derivatives were synthesized by generating two C-N bond in one step to form a ring. These compounds exhibit unnormal large Stocks shift up to240nm independent on the polarity of the solvent. Their solution show orange-red emission around600nm, while the solid powder in the blue and green region. Ml-flu was selected as a luminescent material used in organic light emitting diode (OLED).
In chapter six, indenyl-modified9,10-diphenyl anthracene derivative IN A was designed and synthesized, and its photophysical properties were preliminary studied and compared with 9,10-bis(4-(2,2-diphenylvinyl)phenylanthracene (DPVA).
In chapter seven, conclusion.
利用化学和/或物理方法调控有机材料固态下的发光行为及其产生机制受到了越来越广泛的重视。压致荧光变色材料是一类新型的力刺激响应智能材料,它在信息存储、商标防伪和微应力传感等领域具有潜在的应用,但是具有压致荧光变色性能的有机化合物目前尚十分稀少。本论文主要致力于开发新核结构的聚集诱导发光材料,并通过化学修饰或外部刺激的方法实现固态发光行为的调控,其主要内容概括如下：
第一章重点介绍了激发态分子的光物理过程,并对高效固态发光的有机小分子材料及荧光调控的最新进展进行了综述。
第二章基于对1,1,4,4-四苯基丁二烯结构的修饰,设计合成了四种多取代2,2'-联二茚发光团1a、2a、3a和4a,并充分研究了它们在溶液和固态下的光物理性质。化合物1a-4a在溶液中发光微弱,但是在晶体下发光很强,表现出聚集诱导发光性质。通过缓慢溶剂挥发法,成功获得了化合物1a-4a的单晶。通过单晶结构分析,发现分子在晶体中具有十分扭曲的构型,不存在分子间的p-p堆积作用,导致形成了非紧密堆积结构,这是高效发光的重要原因。化合物1a-3a的晶体发射深蓝色荧光,4a的晶体为绿色；而化合物1a-3a的无定形薄膜红移到天蓝色,4a的无定形薄膜仍为绿色。这表明化合物1a-3a的固态发光依赖于它们的分子构型及堆积状态。进一步研究了化合物1a-3a压致荧光变色性能,并通过粉末X-射线衍射(PXRD)和差式扫描量热法(DSC)的测试验证压致变色的机制。
第三章在上一章的基础上,为了将2,2'-联二茚体系的发光向长波长方向拓展同时获得高效固态发光的BODIPY类荧光团,创新性地将BODIPY基团引入到多取代2,2’-联二茚体系中,设计合成了化合物BDY-IN.化合物BDY-IN仍具有聚集诱导发光性质。利用再沉淀法得到了化合物BDY-IN两种发光差异很大的纳米聚集体,最大发射分别为543nm和646nm,这表明BDY-IN的聚集态发光受聚集形式影响。采用缓慢溶剂挥发法,通过氯仿/乙醇体系中培养出发橙色荧光的单晶BDY-O,最大发射为582nm；通过二氯甲烷/乙醇体系中培养出发红色荧光的单晶BDY-R,最大发射为分别661nm。通过对两种单晶结构的分析发现,BDY-R的分子构型比BDY-O的更为平整且BDY-R的晶体中存在分子间p-p堆积作用,这两个原因导致了BDY-R比BDY-O发光红移约79nm。
第四章设计合成了三种含有三苯乙烯腈和三苯胺基元的化合物CN-TPA、3CN-TPA和4CN-DTPA。研究了三种化合物的聚集诱导发光特性,同时发现了化合物CN-TPA的固体粉末具有压致荧光变色效应。化合物CN-TPA的晶体粉末发蓝绿色荧光(594nm),碾磨可以将其破坏成发黄绿色荧光(545nm)的无定形粉末,再经加热可以恢复成发蓝绿色荧光(594nm)的晶体粉末。粉末X-射线衍射(PXRD)表明化合物CN-TPA的晶体和无定形粉末具有不同的分子堆积模式。差式扫描量热法(DSC)测试显示,晶体是热力学稳定态,而无定形态是亚稳态。采用缓慢溶剂挥发法,获得了化合物CN-TPA发蓝绿色荧光(584nm)的单晶。通过单晶结构分析,发现在晶体中分子构型十分扭曲,导致了形成了非紧密堆积结构；这样,外部压力可以容易地破坏分子构型及堆积模式,从而引起相变。
第五章利用一步生成两根C-N键成环的方法合成了系列稠环取代的N,N’-二芳基吩嗪衍生物(M1-flu、M2-py和M3-phen)。发现该类化合物在溶液中表现出不依赖于溶剂极性的高达240nm的Stocks位移。它们的溶液最大发射在600nm左右,而固体粉末在蓝、绿光区域。以化合物M1-flu作为发光材料初步研究了该类化合物的电致发光性质。
第六章设计合成了茚修饰的9,10-二苯基蒽衍生物INAN,并与参比化合物9,10-二(4-(2,2-二苯乙烯基)苯)蒽DPAV比较,初步研究了其光物理性能。
第七章结论。
As a key component in the organic light-emitting devices (OLEDs), the organic light-emitting materials largely affect the process of industrialization of OLEDs. The organic light-emitting materials are practically used as thin films in OLEDs, so it is of great significance to study and explore organic materials with highly efficient solid state emission. Aggregation-induced emission phenomenon (AIE) offers an effective approach for the development of highly luminous organic materials, and in the past decade a large number of AIE-active dyes based on the core-structure with silole or tetraphenylethene have been developed.
The switching and tuning of organic solid-state fluorescence via chemical and/or physical methods and its mechanism is of great current interest. Mechanochromic fluorescent materials are a class of smart materials with fluorescent properties that change in response to external force stimuli, which could be used in memory chips, sensors, and security inks. However, organic mechanochromic fluorescent materials that are dependent on changes in physical molecular packing modes are extremely rare. This thesis mainly contributes to develop novel core-structures AIE fluorophores, and switch and tune these dyes' solid-state emission through chemical modification or external stimuli. Its main contents summarized as follows.
In chapter one, the photophysical processes of excited molecules are briefly introduced. The latest progress of organic small molecules with highly efficient solid-state emission and various strategies that have been effectively utilized to achieve switchable and tunable fluorescence in the organic solid state are reviewed.
In chapter two, based on the structure of1,1,4,4-tetraphenyl butadiene, four polysubstituted2,2'-biindenyl fluorophores la,2a,3a and4a were designed and synthesized, and their optical properties in solution and solid-state were investigated. Compounds la-4a have the AIE nature. Single crystals of these dyes were obtained by slow solvent evaporation method. The large interplane angles in the cystals make the conformations of la-4a largely deviated from a planar conformation, which prevents molecules from p-p stacking interactions, and thus induces intense emissions in crystal state. The crystals of la-3a show intense blue luminescence, and4a green; while the amorphous film's emission of la-3a red-shift to sky blue, and4a still green. This suggests that solid state emission of compounds la-3a depends on their molecular conformation and packing mode. The mechanochromic ability of la-3a was further examined, and the powder X-ray diffraction (XRD) and differential scanning calorimetry (DSC) measurements were carried out to validate the mechanism of mechanochromism.
In chapter three, based on the last chapter, in order to expand the emission of2,2'-biindenyl derivatives to red region and obtain the BODIPY fluorophore with highly efficient solid state emission, BODIPY moieties were innovatively incorporated into2,2'-biindenyl systems. Bodipy fluorophore BDY-IN was designed and synthesized. BDY-IN still has the AIE nature. Two kinds nano-particles of BDY-IN were prepared by reprecipitation, and they exhibited distinct emission which suggested that the emission of the nano-particles depends on BDY-IN molecular packing mode in the aggregate. The BDY-IN crystals with two polymorphic forms (BDY-O and BDY-R) have been obtained. Due to the more planar conformation and face to face p-p stacking interaction increasing the p-conjugated degree, the emission of BDY-R displays an obvious red shift about79nm compared with BDY-O.
In chapter four, three fluorophores (CN-TPA,3CN-TPA and4CN-DTPA) containing triphenylacrylonitrile and triphenylamines moieties were designed and synthesized. These three dyes are all AIE-active, and CN-TPA display mechanochromism in solid phase. Grinding could disrupt the crystalline CN-TPA with blue-green emission into amorphous CN-TPA with yellow-green emission, and heating treatment could change the amorphous CN-TPA into crystalline CN-TPA. Powder X-ray diffraction (PXRD) characterizations demonstrated that crystalline and amorphous CN-TPA possesses different molecular packing. A differential scanning calorimetry (DSC) measurement revealed that the emission switching was due to the exchange between the thermodynamic-stable crystalline and metastable amorphous states. Single crystals of CN-TPA were gotten by slow solvent evaporation method. The reason for the phase transformation caused by external pressure is ascribed to the twisted conformation of the molecule which leads to poor solid molecular packing and weak interactions in the interfaces of lamellar layers confirmed by its single-crystal X-ray diffraction analysis.
In chapter five, the fused ring substituted N,N-diaryl phenazine derivatives were synthesized by generating two C-N bond in one step to form a ring. These compounds exhibit unnormal large Stocks shift up to240nm independent on the polarity of the solvent. Their solution show orange-red emission around600nm, while the solid powder in the blue and green region. Ml-flu was selected as a luminescent material used in organic light emitting diode (OLED).
In chapter six, indenyl-modified9,10-diphenyl anthracene derivative IN A was designed and synthesized, and its photophysical properties were preliminary studied and compared with 9,10-bis(4-(2,2-diphenylvinyl)phenylanthracene (DPVA).
In chapter seven, conclusion.
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