基于氰基苯乙烯衍生物的功能分子凝胶
摘要
近年来，氰基苯乙烯及其衍生物由于具有特殊的π-共轭结构，易于合成修饰，以及对外部环境敏感的性质而受到人们越来越多的关注。研究发现，大多数氰基苯乙烯类化合物被证实具有聚集诱导荧光增强的性质，并且在聚集态存在较强的分子间π-π堆积作用和氰基作用。在其他分子间相互作用（氢键、范德华力、金属配位等）的协同作用下，氰基苯乙烯及其衍生物易于形成有序的纳微米组装材料。值得注意的是，氰基苯乙烯结构单元易于与其他功能基团或体系的结合，进而使其衍生物在光学器件、传感、生物成像等领域展现出良好的应用前景。本论文以构筑新型的功能分子凝胶体系为目的，将氰基苯乙烯结构单元与具有方向性，强度适中的酰胺基团结合，设计合成了一系列新型的π-共轭氰基苯乙烯衍生物，着重研究它们形成凝胶的自组装特性和功能应用。
首先，我们设计合成了三个具有不同分子构型的氰基苯乙烯酰胺类化合物，线型的PBA、V型的BPIA和星型的TPBTA，分别研究了它们在阴离子识别、聚集荧光增强和凝胶三方面的性质，并探究了分子的构型对上述三种性质的影响。研究发现此类酰胺化合物可以高选择性的比色识别氟离子，并对氯离子、溴离子、碘离子、磷酸二氢根离子、醋酸根离子等其他阴离子表现出显著的抗干扰能力。比色识别的本质主要来自于氟离子对酰胺基团NH的去质子化，同时作为生色基团的氰基苯乙烯将去质子化作用转变成可视的光学信号。虽然分子的构型对此类酰胺化合物在氟离子的选择性识别没有明显的影响，但是对其聚集荧光增强性质表现出显著的影响。化合物BPIA和TPBTA在掺水聚集过程中均表现出明显的聚集荧光增强的性质。在水体积分数为70%时，与星型的TPBTA分子相比，虽然V型的BPIA分子中含有较少的氰基苯乙烯结构单元，却在聚集态表现出相对较高的荧光量子效率。采用加热-冷却法对三者的凝胶化能力进行测试，发现只有星型的TPBTA可以在DMSO/H2O的混合溶剂中形成稳定凝胶，并且所制备的凝胶显示出显著的聚集诱导荧光增强性质，这充分表明氰基苯乙烯结构单元具有构筑成多功能组装材料的潜力。另外，其干凝胶的纤维网络结构可以有效的吸附水中的染料分子（甲基紫），这为处理污水中的有害物质提供了研究基础。
其次，在V型结构BPIA的研究基础上，我们通过改变间苯二甲酸的端位取代基团（强极性的硝基和大体积的叔丁基）来调节分子在有机溶剂中的溶解与结晶平衡，从而成功地构筑了一类既不带胆甾又不含长烷基链的功能性凝胶因子。强极性硝基基团的引入，有利于增强分子间的作用，促使化合物BPNIA在不同的溶剂中既可以形成超声诱导凝胶又可以形成热致凝胶。利用氟离子对酰胺基团NH的去质子化作用，实现了BPNIA的凝胶对氟离子的双通道识别，即凝胶-溶液的转变和颜色的变化。同时质子性溶剂的加入又可使体系由溶液转变为凝胶，凝胶形态、颜色均可以复原。可逆的凝胶-溶液转变及显著的颜色变化是由氟离子和质子共同控制的。由此，我们得到了多刺激和多响应的超分子凝胶体系。空间立体结构较大的叔丁基基团的引入，增大了聚集态时分子间的距离，进而调节了分子在有机溶剂中的溶解-沉淀平衡，并促使BPBIA在三氯甲烷、二氯甲烷、二氯乙烷、乙腈、二氧六环等五种溶剂中形成凝胶。此外，通过简单地溶液挥发法，可以得到单分散、无杂质、形貌均一的超长一维荧光纳米线。单晶结构分析表明，上述分子的一维组装优势是制得纳米纤维及超长纳线的主要原因之一。值得注意的是所制备的凝胶纤维和一维纳米线在紫外光照射下都能发射出蓝色荧光，这为其在发光材料、荧光传感器等方面的应用奠定了基础。
然后，我们将氰基苯乙烯与常见的凝胶结构单元胆固醇结合，设计合成了一类具有聚集荧光增强性质的ALS型凝胶因子。通过改变芳香基团（A）研究了π-共轭结构的变化对分子成胶能力的影响。利用2,7-萘二酚的酚羟基与凝胶因子中酰胺基团和氰基的作用，实现了凝胶对中性分子2,7-萘二酚的双通道识别，即凝胶-沉淀的转变和荧光消失。这种由凝胶相态转变引起的裸眼检测具有简便、快捷的特点，为2,7-萘二酚的识别提供了一种新的方法。基于π-共轭结构较大的化合物G2在芳香类有机溶剂中具有极强的成胶能力，我们通过引入辅助剂THF，实现了室温下芳香类溶剂与水的分离以及芳香类溶剂的回收。利用G2的相选择凝胶的性质，简便地净化了有机染料罗丹明B污染的水资源。这部分工作为设计具有新型功能的凝胶因子提供了思路。
Cyanostilbene and its derivatives have received great research attention becauseof their unique multi-responsive, modifiable and luminescent characteristics. Mostcyanostilbene-based compounds can produce typical aggregation-induced enhancedemission (AIEE) in the aggregated or solid states. It should be pointed out that thecyano moiety has the ability to interact with either other cyano groups or hydrogens inaromatic rings. The cyano interaction could cooperate with other intermolecularinteractions such as π-π stacking, to fabricate supramolecular architectures. On thebasis of their unique feature and easily bonded with other units or systems,cyanostilbene and its derivatives are promising to be used in optoelectronic devices,chemosensors and biological imaging. In order to obtain a new class ofsupramolecular gelators based on cyanostilbene amide derivatives, we combine thecyanostilbene with amide group to increase the intermolecular interactions.
First of all, we synthesized three kinds of cyanostilbene amide derivatives withdifferent molecular structures, and studied their properties in anion recognition, AIEE,and self-assemble. It was found that these cyanostilbene amide derivatives can act ashighly selective colorimetric sensors for fluoride ion, overcoming the interference ofH2PO4, AcO and other halide ions. The deprotonation of the NH groups induced byfluoride ion is responsible for the dramatic color change from colorless to yellow. Thedifferent molecular structures did not affect the detection of fluoride ion, but played asignificant role in their AIEE and self-assembly properties. Both BPIA and TPBTAexhibited typical AIEE in the aggregated state, but the conpound BPIA showed higherfluorescence quantum efficiency than that of TPBTA with three cyanostilbene unitswhen the water volume fraction is70%. Compared with PBA and BPIA, only TPBTAcan readily self-assemble into gels with nanofibers structure in the mixed solvents ofDMSO/H2O. Interestingly, the xerogels prepared from the TPBTA organogels showeda striking property of adsorbing crystal violet dyes from water. This dye-adsorptionability of gelators can be utilized in water purification by removing toxic dyes from wastewater.
Secondly, we synthesized a novel class of gelators based on V-shapedcyanostilbene amide derivatives without steroidal units and long alkyl chains throughchanging the isophthalic acid substituted group (a highly polar nitro group and a largevolume of tert-butyl group) to favor the balance between their solubility andcrystallization. The introduction of strong polar nitro group may enhance theintermolecular interactions, which make BPNIA form thermoreversible gel inDMSO/H2O and ultrasound-stimulated gel in DMSO by the cooperative interplay ofintermolecular hydrogen bonding, π–π stacking and cyano interactions. On the basisof the deprotonation of NH groups induced by fluoride ion, introducing of fluoride notonly changed the color of the system but also disrupted the preformed gel to solution.Subsequently, the addition of polar protic solvents could make the solution regelatedand the red color faded. Therefore, the reversible gel-sol transition and noticeablecolor change were controlled by the use of fluoride stimulus and proton control. Theintroduction of larger steric hindrance of tert-butyl group not only may weaken thetight molecular stacking and strong intermolecular interactions, but also could balancethe solubility and deposition, leading to the formation of the gel. Meanwhile,well-defined ultralong1D nanowires of BPBIA with lengths up to several millimetersalso have been fabricated from a simple slow evaporation approach. More importantly,the individually-dispersed nanowires with uniform morphology are independent ofsubstrates and solvents. The single-crystal X-ray analysis of compound BPBIAprovided reasonable explanation for the formation of1D nano-or microstructures. Itis worth noting that the generated nanofibrous gels and the nanowires emit strong bluelight under UV irradiation, revealing that these1D nanomaterials show potentialapplications in emitting materials as well as fluorescent chemosensors.
Finally, we synthesized a class of ALS-type organic gelators based oncyanostilbene amide derivatives and studied the influence of π-conjugated structureon their gellability by changing the aromatic groups. It was found that the compoundG2with larger π-conjugated structure showed great ability to gel a variety of organic observed for compounds G2after gelation. Owing to the phenolic hydroxyl of2,7-naphthalenediol could destroy the intermolecular hydrogen bonds and cyanointeractions between gelators, the organogel of G2exhibited a high selectivitytowards2,7-naphthalenediol instead of the other phenolic derivatives, which exhibiteda two channel response through gel–sol transition and fluorescence disappearance.Such responsive systems are highly desirable for the development of sensor devices orin applications like drug delivery. Additionally, G2showed phase-selective gelationproperties in aromatic solvents–water mixtures at room temperature by introducing ofthe assistant solvent. Most importantly the gelator molecule can be recovered andreused several times, indicating its potential application in collection of aromaticsolvents and purification of water. Interestingly, the gelator G2can purify water viaphase-selective gelation process. Thus, this part of work offers a new way fordesigning new functional gelators.
首先，我们设计合成了三个具有不同分子构型的氰基苯乙烯酰胺类化合物，线型的PBA、V型的BPIA和星型的TPBTA，分别研究了它们在阴离子识别、聚集荧光增强和凝胶三方面的性质，并探究了分子的构型对上述三种性质的影响。研究发现此类酰胺化合物可以高选择性的比色识别氟离子，并对氯离子、溴离子、碘离子、磷酸二氢根离子、醋酸根离子等其他阴离子表现出显著的抗干扰能力。比色识别的本质主要来自于氟离子对酰胺基团NH的去质子化，同时作为生色基团的氰基苯乙烯将去质子化作用转变成可视的光学信号。虽然分子的构型对此类酰胺化合物在氟离子的选择性识别没有明显的影响，但是对其聚集荧光增强性质表现出显著的影响。化合物BPIA和TPBTA在掺水聚集过程中均表现出明显的聚集荧光增强的性质。在水体积分数为70%时，与星型的TPBTA分子相比，虽然V型的BPIA分子中含有较少的氰基苯乙烯结构单元，却在聚集态表现出相对较高的荧光量子效率。采用加热-冷却法对三者的凝胶化能力进行测试，发现只有星型的TPBTA可以在DMSO/H2O的混合溶剂中形成稳定凝胶，并且所制备的凝胶显示出显著的聚集诱导荧光增强性质，这充分表明氰基苯乙烯结构单元具有构筑成多功能组装材料的潜力。另外，其干凝胶的纤维网络结构可以有效的吸附水中的染料分子（甲基紫），这为处理污水中的有害物质提供了研究基础。
其次，在V型结构BPIA的研究基础上，我们通过改变间苯二甲酸的端位取代基团（强极性的硝基和大体积的叔丁基）来调节分子在有机溶剂中的溶解与结晶平衡，从而成功地构筑了一类既不带胆甾又不含长烷基链的功能性凝胶因子。强极性硝基基团的引入，有利于增强分子间的作用，促使化合物BPNIA在不同的溶剂中既可以形成超声诱导凝胶又可以形成热致凝胶。利用氟离子对酰胺基团NH的去质子化作用，实现了BPNIA的凝胶对氟离子的双通道识别，即凝胶-溶液的转变和颜色的变化。同时质子性溶剂的加入又可使体系由溶液转变为凝胶，凝胶形态、颜色均可以复原。可逆的凝胶-溶液转变及显著的颜色变化是由氟离子和质子共同控制的。由此，我们得到了多刺激和多响应的超分子凝胶体系。空间立体结构较大的叔丁基基团的引入，增大了聚集态时分子间的距离，进而调节了分子在有机溶剂中的溶解-沉淀平衡，并促使BPBIA在三氯甲烷、二氯甲烷、二氯乙烷、乙腈、二氧六环等五种溶剂中形成凝胶。此外，通过简单地溶液挥发法，可以得到单分散、无杂质、形貌均一的超长一维荧光纳米线。单晶结构分析表明，上述分子的一维组装优势是制得纳米纤维及超长纳线的主要原因之一。值得注意的是所制备的凝胶纤维和一维纳米线在紫外光照射下都能发射出蓝色荧光，这为其在发光材料、荧光传感器等方面的应用奠定了基础。
然后，我们将氰基苯乙烯与常见的凝胶结构单元胆固醇结合，设计合成了一类具有聚集荧光增强性质的ALS型凝胶因子。通过改变芳香基团（A）研究了π-共轭结构的变化对分子成胶能力的影响。利用2,7-萘二酚的酚羟基与凝胶因子中酰胺基团和氰基的作用，实现了凝胶对中性分子2,7-萘二酚的双通道识别，即凝胶-沉淀的转变和荧光消失。这种由凝胶相态转变引起的裸眼检测具有简便、快捷的特点，为2,7-萘二酚的识别提供了一种新的方法。基于π-共轭结构较大的化合物G2在芳香类有机溶剂中具有极强的成胶能力，我们通过引入辅助剂THF，实现了室温下芳香类溶剂与水的分离以及芳香类溶剂的回收。利用G2的相选择凝胶的性质，简便地净化了有机染料罗丹明B污染的水资源。这部分工作为设计具有新型功能的凝胶因子提供了思路。
Cyanostilbene and its derivatives have received great research attention becauseof their unique multi-responsive, modifiable and luminescent characteristics. Mostcyanostilbene-based compounds can produce typical aggregation-induced enhancedemission (AIEE) in the aggregated or solid states. It should be pointed out that thecyano moiety has the ability to interact with either other cyano groups or hydrogens inaromatic rings. The cyano interaction could cooperate with other intermolecularinteractions such as π-π stacking, to fabricate supramolecular architectures. On thebasis of their unique feature and easily bonded with other units or systems,cyanostilbene and its derivatives are promising to be used in optoelectronic devices,chemosensors and biological imaging. In order to obtain a new class ofsupramolecular gelators based on cyanostilbene amide derivatives, we combine thecyanostilbene with amide group to increase the intermolecular interactions.
First of all, we synthesized three kinds of cyanostilbene amide derivatives withdifferent molecular structures, and studied their properties in anion recognition, AIEE,and self-assemble. It was found that these cyanostilbene amide derivatives can act ashighly selective colorimetric sensors for fluoride ion, overcoming the interference ofH2PO4, AcO and other halide ions. The deprotonation of the NH groups induced byfluoride ion is responsible for the dramatic color change from colorless to yellow. Thedifferent molecular structures did not affect the detection of fluoride ion, but played asignificant role in their AIEE and self-assembly properties. Both BPIA and TPBTAexhibited typical AIEE in the aggregated state, but the conpound BPIA showed higherfluorescence quantum efficiency than that of TPBTA with three cyanostilbene unitswhen the water volume fraction is70%. Compared with PBA and BPIA, only TPBTAcan readily self-assemble into gels with nanofibers structure in the mixed solvents ofDMSO/H2O. Interestingly, the xerogels prepared from the TPBTA organogels showeda striking property of adsorbing crystal violet dyes from water. This dye-adsorptionability of gelators can be utilized in water purification by removing toxic dyes from wastewater.
Secondly, we synthesized a novel class of gelators based on V-shapedcyanostilbene amide derivatives without steroidal units and long alkyl chains throughchanging the isophthalic acid substituted group (a highly polar nitro group and a largevolume of tert-butyl group) to favor the balance between their solubility andcrystallization. The introduction of strong polar nitro group may enhance theintermolecular interactions, which make BPNIA form thermoreversible gel inDMSO/H2O and ultrasound-stimulated gel in DMSO by the cooperative interplay ofintermolecular hydrogen bonding, π–π stacking and cyano interactions. On the basisof the deprotonation of NH groups induced by fluoride ion, introducing of fluoride notonly changed the color of the system but also disrupted the preformed gel to solution.Subsequently, the addition of polar protic solvents could make the solution regelatedand the red color faded. Therefore, the reversible gel-sol transition and noticeablecolor change were controlled by the use of fluoride stimulus and proton control. Theintroduction of larger steric hindrance of tert-butyl group not only may weaken thetight molecular stacking and strong intermolecular interactions, but also could balancethe solubility and deposition, leading to the formation of the gel. Meanwhile,well-defined ultralong1D nanowires of BPBIA with lengths up to several millimetersalso have been fabricated from a simple slow evaporation approach. More importantly,the individually-dispersed nanowires with uniform morphology are independent ofsubstrates and solvents. The single-crystal X-ray analysis of compound BPBIAprovided reasonable explanation for the formation of1D nano-or microstructures. Itis worth noting that the generated nanofibrous gels and the nanowires emit strong bluelight under UV irradiation, revealing that these1D nanomaterials show potentialapplications in emitting materials as well as fluorescent chemosensors.
Finally, we synthesized a class of ALS-type organic gelators based oncyanostilbene amide derivatives and studied the influence of π-conjugated structureon their gellability by changing the aromatic groups. It was found that the compoundG2with larger π-conjugated structure showed great ability to gel a variety of organic observed for compounds G2after gelation. Owing to the phenolic hydroxyl of2,7-naphthalenediol could destroy the intermolecular hydrogen bonds and cyanointeractions between gelators, the organogel of G2exhibited a high selectivitytowards2,7-naphthalenediol instead of the other phenolic derivatives, which exhibiteda two channel response through gel–sol transition and fluorescence disappearance.Such responsive systems are highly desirable for the development of sensor devices orin applications like drug delivery. Additionally, G2showed phase-selective gelationproperties in aromatic solvents–water mixtures at room temperature by introducing ofthe assistant solvent. Most importantly the gelator molecule can be recovered andreused several times, indicating its potential application in collection of aromaticsolvents and purification of water. Interestingly, the gelator G2can purify water viaphase-selective gelation process. Thus, this part of work offers a new way fordesigning new functional gelators.
引文
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