荧光可控的π-共轭有机凝胶体系的构筑
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摘要
本论文以合成π-共轭有机凝胶剂为出发点,以构筑荧光可调控的功能性有机凝胶体系为目的,设计并合成了一系列咔唑类和吩噻嗪类有机凝胶剂,并将能量受体引入到具有光捕获能力的咔唑凝胶体系中,构建了新型的光捕获体系,取得的创新性的研究结果如下:
合成了一系列咔唑衍生物,并对其自组装和光物理性质进行了研究,发现叔丁基在咔唑衍生物的凝胶化过程中起到了十分重要的作用,其大的空间效应可以加大聚集态中咔唑环之间的距离,从而调节分子在有机溶剂中的溶解-沉淀平衡,利于凝胶的形成。该工作为通过调控分子间作用力来设计新型功能软材料提供了新思路。所制备的咔唑类凝胶具有显著的聚集诱导荧光增强性质。
首次合成了刚性树枝状有机凝胶剂,讨论了树枝代数对其凝胶性质的影响,发现第2代咔唑树突在超声条件下形成稳定的凝胶,并且凝胶纤维能够发射较强的蓝绿色荧光;第1代咔唑树突只能在1,6-己二胺辅助下形成稳定的二元凝胶,得到的凝胶能发射强的蓝色荧光;第3代咔唑树突由于空间结构的特殊性难于自组装,不具备成凝胶能力。
利用超分子自组装技术构筑了一维光捕获体系,其中,作为天线分子的叔丁基咔唑衍生物可作为脚手架使能量受体-吩噻嗪功能化的吡咯并吡咯二酮衍生物均匀生长在凝胶纤维上,从而将其激发态能量部分传递给受体分子,通过调节激发波长实现了对复合凝胶发光颜色的调控。
以刚性树枝状咔唑为光捕获天线,以苝二酰亚胺衍生物为能量受体,构筑了具有白光发射能力的复合有机凝胶。该工作为通过调控给受体之间的能量转移效率来构筑微观有序的白光材料提供了新途径。
合成了D-π-A型吩噻嗪和咔唑衍生物,研究了它们的成凝胶能力和光物理性质。发现含有较长碳链的吩噻嗪甲酰胺衍生物能在超声波诱导下使有机溶剂凝胶化,且在凝胶的形成过程中出现了不同寻常的聚集诱导荧光蓝移的现象,这是TICT激发态在凝胶相中受到抑制的结果。
Recently,π-conjugated organogels have attracted considerable attentions in the supremolecular chemistry, because of their unique self-assembly structures and controllable optoelectronic properties.π-Conjugated organogelators can self-assemble into various dimensional and morphologic superstructures in organic solvents directed by noncovalent interactions such as H-bonding, vander Walls,π-πstacking ect. The supramolecular self-assembly ofπ-conjugated organogelors can attribute many new features beyond the single molecules. Meanwhile,π-conjugated organogelators could be selectively functionalized with the introduction of desired moieties so as to build up target system with various properties, which possess specific applications in light harvesting, energy and charge transfer, and switches.
Herein, we have designed and synthesized a series of carbazole-based and phenothiazine-based organogelators, which can self-assembled into well-orderedπ-gels with controllable fluorescence emission. In order to mimic the natural light-harvesting system, diaryldiketopyrrolopyrrole and perylene-carboxylic diimides derivative were introduced into the obtained carbazole-based organogels. Some creative results have been obtained, and the main points are outlined below:
(1) A series of carbazole derivatives were synthesized and their self-assembling as well as photophysical properties were investigated. It was found that the monomeric and dimeric carbazoles containing tert-butyl groups could gelatize some organic solvents, but the ones without tert-butyl groups could not form organogels, indicating that the tert-butyl unit plays a key role in the formation of the organogels. We suggested that the large spatial effect can enlarge the distance between aromatic moieties and weaken theπ-πinteraction between carbazoles, which may balance the solubility and deposition to lead to the formation of the gel. Based on the results of IR, UV-Vis and XRD, the possible molecular packing model was proposed. It is worth noting that the aggregation-induced-emission was detected during the process of gelation, which could be ascribed to a combination of the formation of J-aggregate, enhancement of planarization and the restriction of rotation of single bond in the chromophores. This work supplies a new way to design novel functional soft materials by controlling the intermolecular interaction.
(2) We firstly synthesized rigid dendritic gelators based on oligocarbazoles, and the influence of the generation of dendron on their gelation ability was investigted. It was found that second generation of carbazole dendron could form gel by ultrasonic stimulus, and the obtained gel can emit strong blue-green light. The first generation of carbazole dendron can only form two-component gel assisted by 1,6-hexamethylenediamine, and the obtained gel can emit strong blue light. The third generation of carbazole dendron can not gelatinize any solvents owing to special spatial conformation.
(3) We generated well-ordered 1D arrays based on carbazole and diaryldiketopyrrolopyrrole derivatives in order to mimic the natural light-harvesting system, in which carbazole-based organogel was used as a scaffold to make diaryldiketopyrrolopyrrole grow up along the gel fibers. In the composite gel, partial excitation energy transfer from carbazole-based organogelator, the light-harvesting antenna, to the diaryldiketopyrrolopyrrole derivatives, the acceptor, occurred. Notably, the composite gel could emit intense red light or purplish white light by tuning the excitation wavelength. It provided a simple way to fabricate functional supramolecular arrays. Such ordered soft materials with various emitting colors may have potential applications in sensor and photonic devices.
(4) A white-light-emitting organogel system based on rigid dendritic carbazole-based gelator and diaryldiketopyrrolopyrrole derivatives was fabricated. In the composite gel, partial excitation energy transfer occurred from energy donor of carbazole-based organogelator with bluish green emission, to the diaryldiketopyrrolopyrrole derivatives, the acceptor, with red emission, leading to a white-light-emitting organogel. The energy transfer efficiency could be tuned by adjusting the intermolecular interaction between energy donor and acceptor, which provided a simple way to fabricate white-light-emitting soft material.
(5) Phenothiazine and carbazole derivatives were synthesized, and their gelation ability and photophysical properties were investigated. It was found that phenothiazine formamide derivative with long carbon chain can gelatinize n-henxane, cyclohexane and enthanol/water by untrasonic stimulus. Notably, compared to the solution, the fluorescence emission of the gel phase bule shifted significantly, which were attributed to the suppression of TICT. Such functional soft material may possess potential applications in sensors.
合成了一系列咔唑衍生物,并对其自组装和光物理性质进行了研究,发现叔丁基在咔唑衍生物的凝胶化过程中起到了十分重要的作用,其大的空间效应可以加大聚集态中咔唑环之间的距离,从而调节分子在有机溶剂中的溶解-沉淀平衡,利于凝胶的形成。该工作为通过调控分子间作用力来设计新型功能软材料提供了新思路。所制备的咔唑类凝胶具有显著的聚集诱导荧光增强性质。
首次合成了刚性树枝状有机凝胶剂,讨论了树枝代数对其凝胶性质的影响,发现第2代咔唑树突在超声条件下形成稳定的凝胶,并且凝胶纤维能够发射较强的蓝绿色荧光;第1代咔唑树突只能在1,6-己二胺辅助下形成稳定的二元凝胶,得到的凝胶能发射强的蓝色荧光;第3代咔唑树突由于空间结构的特殊性难于自组装,不具备成凝胶能力。
利用超分子自组装技术构筑了一维光捕获体系,其中,作为天线分子的叔丁基咔唑衍生物可作为脚手架使能量受体-吩噻嗪功能化的吡咯并吡咯二酮衍生物均匀生长在凝胶纤维上,从而将其激发态能量部分传递给受体分子,通过调节激发波长实现了对复合凝胶发光颜色的调控。
以刚性树枝状咔唑为光捕获天线,以苝二酰亚胺衍生物为能量受体,构筑了具有白光发射能力的复合有机凝胶。该工作为通过调控给受体之间的能量转移效率来构筑微观有序的白光材料提供了新途径。
合成了D-π-A型吩噻嗪和咔唑衍生物,研究了它们的成凝胶能力和光物理性质。发现含有较长碳链的吩噻嗪甲酰胺衍生物能在超声波诱导下使有机溶剂凝胶化,且在凝胶的形成过程中出现了不同寻常的聚集诱导荧光蓝移的现象,这是TICT激发态在凝胶相中受到抑制的结果。
Recently,π-conjugated organogels have attracted considerable attentions in the supremolecular chemistry, because of their unique self-assembly structures and controllable optoelectronic properties.π-Conjugated organogelators can self-assemble into various dimensional and morphologic superstructures in organic solvents directed by noncovalent interactions such as H-bonding, vander Walls,π-πstacking ect. The supramolecular self-assembly ofπ-conjugated organogelors can attribute many new features beyond the single molecules. Meanwhile,π-conjugated organogelators could be selectively functionalized with the introduction of desired moieties so as to build up target system with various properties, which possess specific applications in light harvesting, energy and charge transfer, and switches.
Herein, we have designed and synthesized a series of carbazole-based and phenothiazine-based organogelators, which can self-assembled into well-orderedπ-gels with controllable fluorescence emission. In order to mimic the natural light-harvesting system, diaryldiketopyrrolopyrrole and perylene-carboxylic diimides derivative were introduced into the obtained carbazole-based organogels. Some creative results have been obtained, and the main points are outlined below:
(1) A series of carbazole derivatives were synthesized and their self-assembling as well as photophysical properties were investigated. It was found that the monomeric and dimeric carbazoles containing tert-butyl groups could gelatize some organic solvents, but the ones without tert-butyl groups could not form organogels, indicating that the tert-butyl unit plays a key role in the formation of the organogels. We suggested that the large spatial effect can enlarge the distance between aromatic moieties and weaken theπ-πinteraction between carbazoles, which may balance the solubility and deposition to lead to the formation of the gel. Based on the results of IR, UV-Vis and XRD, the possible molecular packing model was proposed. It is worth noting that the aggregation-induced-emission was detected during the process of gelation, which could be ascribed to a combination of the formation of J-aggregate, enhancement of planarization and the restriction of rotation of single bond in the chromophores. This work supplies a new way to design novel functional soft materials by controlling the intermolecular interaction.
(2) We firstly synthesized rigid dendritic gelators based on oligocarbazoles, and the influence of the generation of dendron on their gelation ability was investigted. It was found that second generation of carbazole dendron could form gel by ultrasonic stimulus, and the obtained gel can emit strong blue-green light. The first generation of carbazole dendron can only form two-component gel assisted by 1,6-hexamethylenediamine, and the obtained gel can emit strong blue light. The third generation of carbazole dendron can not gelatinize any solvents owing to special spatial conformation.
(3) We generated well-ordered 1D arrays based on carbazole and diaryldiketopyrrolopyrrole derivatives in order to mimic the natural light-harvesting system, in which carbazole-based organogel was used as a scaffold to make diaryldiketopyrrolopyrrole grow up along the gel fibers. In the composite gel, partial excitation energy transfer from carbazole-based organogelator, the light-harvesting antenna, to the diaryldiketopyrrolopyrrole derivatives, the acceptor, occurred. Notably, the composite gel could emit intense red light or purplish white light by tuning the excitation wavelength. It provided a simple way to fabricate functional supramolecular arrays. Such ordered soft materials with various emitting colors may have potential applications in sensor and photonic devices.
(4) A white-light-emitting organogel system based on rigid dendritic carbazole-based gelator and diaryldiketopyrrolopyrrole derivatives was fabricated. In the composite gel, partial excitation energy transfer occurred from energy donor of carbazole-based organogelator with bluish green emission, to the diaryldiketopyrrolopyrrole derivatives, the acceptor, with red emission, leading to a white-light-emitting organogel. The energy transfer efficiency could be tuned by adjusting the intermolecular interaction between energy donor and acceptor, which provided a simple way to fabricate white-light-emitting soft material.
(5) Phenothiazine and carbazole derivatives were synthesized, and their gelation ability and photophysical properties were investigated. It was found that phenothiazine formamide derivative with long carbon chain can gelatinize n-henxane, cyclohexane and enthanol/water by untrasonic stimulus. Notably, compared to the solution, the fluorescence emission of the gel phase bule shifted significantly, which were attributed to the suppression of TICT. Such functional soft material may possess potential applications in sensors.
引文
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