含三亚苯基超分子和两亲性星形聚合物的制备及自组装研究
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摘要
超分子自组装被认为是具有发展前景的制备功能材料的新方法之一。因此进行分子单元组成和结构的设计,利用非共价作用构筑新型超分子体系,是目前超分子化学研究的热点。离子键是一种较强的非共价键作用,利用它制备超分子更加快捷。与其它超分子相比,离子键超分子具有热稳定性高、对于pH敏感、在适当的条件下具有可逆性,可以用作智能材料。离子键超分子化合物的研究报道相对来说还比较少,特别是离子键超分子星形聚合物鲜见报道,需要探索研究它的有效制备方法。本论文从分子结构设计出发,合成了以三亚苯基单元为核的离子键超分子化合物和星形超分子聚合物,研究了它们的溶液自组装行为。通过本研究工作,可以加深对离子键超分子形成规律的认识和理解,为新的功能材料的设计和制备提供基础。本论文的主要内容可以分为六个部分:
一、合成了含有六个叔胺基的盘状三亚苯衍生物2,3,6,7,10,11-六(N,N-二甲氨基丙氨基羰基甲氧基)三亚苯(HDTP),将其分别和带有不同数目取代基的苯甲酸衍生物(对十二烷氧基苯甲酸、3,5-二十二烷氧基苯甲酸和3,4,5-三十二烷氧基苯甲酸)作用,合成了六臂,十二臂和十八臂离子键盘状超分子化合物。通过核磁共振氢谱和红外光谱确定了它们的结构。用透射电镜和紫外吸收光谱研究了这些离子键超分子化合物在甲苯溶液中自组装行为。实验结果表明,六臂的盘状超分子化合物能自身组装成片层结构,并使溶剂凝胶化,而十二臂和十八臂盘状超分子化合物在甲苯溶液中聚集成不同长度的纳米纤维,且随着臂数的增多纤维尺寸变短。这是由于过多的烷基链降低超分子化合物的聚集能力,影响了聚集态的形成。
二、用HDTP和对十二烷氧基二联苯甲酸(DBC)作为原料,成功的制备了离子键盘状超分子化合物HDTP/DBC。该超分子化合物能使苯、甲苯、二甲苯等芳烃溶剂形成稳定的凝胶。通过透射电镜和扫描电镜观察到它们在对二甲苯中自组装形成了直径为50到130纳米的纤维聚集体,这些纳米纤维进一步交联形成三维网络结构。对照试验表明,通过DBC组分的长链烷烃的引入有效地增加了超分子化合物在芳烃溶剂中的溶解能力。红外光谱,紫外可见光谱和荧光光谱研究显示,氢键和π-π相互作用是该离子键超分子自组装和凝胶化的主要驱动力。基于实验结果,我们对这种二组分凝胶相结构的形成机理提出了可能性的模型。
三、合成了多官能团衍生物,2,3,6,7,10,11-六(羧酸基甲氧基)三亚苯(HCTP),将它与多官能团三亚苯衍生物HDTP反应,成功地获得了二组分盘状超分子HDTP/HCTP,其结构用红外光谱和核磁氢谱进行了表征。通过紫外可见光谱和荧光光谱的测定说明,三亚苯单元间的π-π堆积作用和盘状分子侧链间的多重离子作用共同促使了两种构筑单元以1:1的摩尔比,面对面地排列形成了维柱状结构聚集体。通过透射电镜观察到了盘状超分子在水溶液中组装形成的三维纤维状聚集结构。
四、采用模板导向组装技术,以三亚苯衍生物HDTP为核和端羧基聚乙二醇(PEG-COOH)作用,成功地合成了六臂离子键盘状超分子星形聚合物HDTP/PEG-COOH。用红外光谱、核磁共振氢谱和凝胶渗透色谱对聚合物的结构进行了表征。通过实验发现,这种超分子聚合物在去离子水、氯仿和甲苯的溶液中能自组装形成球状聚集体,从透射电镜照片上观察到聚集体的尺寸随着溶剂极性的降低而增大。通过荧光光谱的测量发现,荧光强度随着溶剂的极性降低而发生淬灭现象。这与共价键合成的盘状化合物的聚集行为正好相反,说明聚合物中离子键的引入降低了溶质分子与低极性溶剂之间的相互作用,促进了溶质分子自身的聚集。
五、成功地将可逆加成断裂链转移(RAFT)聚合用于离子键超分子星形聚合的制备。首先把三硫代碳酸酯的羧酸衍生物(DMP)与三亚苯衍生物HDTP进行反应,得到了离子键星形超分子链转移剂。在链转移剂的存在下分别进行丙烯酸叔丁酯(tBA)和苯乙烯(St)的RAFT聚合反应,成功地合成出六臂离子键超分子星形聚合物TP(PtBA)_6、TP(PSt)_6、TP(PtBA-b-PSt)_6。聚合物的结构和分子量通过红外光谱、核磁共振氢谱和凝胶渗透色谱进行了表征,结果显示聚合反应具有活性特征,聚合物结构明确,分子量分布较窄(1.02—1.11)。
六、合成了六官能团原子转移自由基聚合(ATRP)引发剂,2,3,6,7,10,11-六(2-溴丙酰基)三亚苯(HBTP),将其用于引发甲基丙烯酸二甲氨基乙酯(DMAEMA)和苯乙烯(St)的聚合,制备了结构明确、分子量分布窄的两亲性星形嵌段聚合物TP(PDMAEMA)_6和TP(PDMAEMA-b-PSt)_6。考察了两亲性星形嵌段共聚物TP(PDMAEMA-b-PSt)_6在溶液中的自组装行为。从电镜照片观察到,在中性水溶液中形成了球和碗状共存的聚集体,这可用粘度控制机理解释。而在稀盐酸溶液中,自组装成了球形反相胶束,这是由于质子化PDMAEMA嵌段能提高超分子在水溶液中的溶解性,有利于较大尺寸反相胶束的形成。不过在三氟乙酸水溶液中,自组装成的球形反相胶束尺寸较小,这是由于三氟甲基的疏水特性所致。
Supramolecular self-assembly is considered to be an efficient strategy to prepare functional materials,in which molecules associate spontaneously into ordered aggregates as a result of noncovalent interactions.The design of materials through self-assembly processes is becoming one of the primary frontiers of supramolecular chemistry.Otherwise,ionic bond is well known as the strongest noncovalent interactions and sensitive to pH.However,so far ionic interactions have largely been neglected in synthesis of supramolecules,especially for ion-bonded supramolecular star polymers,although they have some distinct characteristics,such as fast and facile functionalization,reversibility,self-reparability and environment sensitivity.In this thesis,we designed and synthesized a series of supramolecules by molecular recognition method,which was formed by combining discotic triphenylene derivatives and guest molecules through ionic interaction.Their self-assembly properties in solution were investigated.There are six main parts included in this thesis.
The first part is concentrated on the synthesis a family of discotic supramolecular compounds consisting of 2,3,6,7,10,11-hexakis(N,N-dimethylaminopropylaminocarbonylmethoxy)triphenylene (HDTP) and 4-dodecyloxy-, 3,5-didodecyloxy-,and 3,4,5-tridodecyloxy-benzoic acids via molecular recognition. The structures of resulting products were characterized by Fourier transformation infrared(FTIR) spectra and proton NMR(~1H NMR) spectra.Moreover,their self-assembly behaviors in toluene were investigated by means of transmission electron micrograph(TEM) and UV-vis measurement.Discoctic supramolecular compound with mono-dodecyloxybenzoate units can make solvent gelation and large sheet-like structure was observed,while supramolecular compound with di-and tridodecyloxybenzoate moieties self-assembled into stable nanofibers with different length.It was suggested that the alkyl chains promoted the solubility of supramolecular compound but make against the formation of order aggregates.
The second part shows a novel two-component organgelator.At first,an ion-bonded discotic supramolecular compound was successfully prepared from HDTP and 4'-dodecyloxybiphenyl-4-carboxylic acid(DBC) by ionic self-assembly route.We found that the supramolecular compound can self-assemble into stable gels in aromatic hydrocarbons,such as benzene,toluene,and xylene.Nanofibers with diameters of 50-130 nm were observed in the p-xylene gels by TEM and SEM.The FTIR data in conjunction with UV-vis and fluorescence spectra suggested that the aggregation of the complex into elongated fibers in solution was induced by a directional extended network of hydrogen bonds,π-πinteractions and van der waals force.Based on the experiment analysis,we proposed a tentative self-assembly model of this two-component gel-phase material.
In the third part,we chose two triphenylene-based derivatives with opposite charges,HDTP and 2,3,6,7,10,11-hexakis(carbonylmethoxy)triphenylene(HCTP),to achieve a novel two-component discotic supramolecule by molecular recognition. The structure was checked by FTIR and ~1H NMR.UV-vis together with FL measurement confirmed that the combination of ionic interactions andπ-πinteractions drove two building blocks to construct one-dimensional columnar stacks. TEM image showed a large three-dimensional fibrillar network from aqueous solution,which was composed by the long strands with micrometers in length and approximately 100-160 nm wide.
The forth part describes theπ-conjugated template promoted the formation and self-assembly of well-defined polymer.HDTP was selected as template and combined with PEG-COOH via complementary molecular recognition to provide an ion-bonded discotic supramolecular star polymer HDTP/PEG-COOH.The structure of the resulting polymer was confirmed by ~1H NMR,FTIR and gel permeation chromatography(GPC).The self-assembly behaviors of the supramolecular polymer in deionized water,chloroform,and toluene were investigated.Spherical aggregations were observed by TEM in all solution.Their diameter increases with decrease of the polarity of solvent.UV-vis and fluorescence spectra indicated thatπ-πinteractions between aromatic units play important roles in the formation of aggregates. Fluorescence spectra in different solution further suggest that low polar solvent favorable to enhance more strong ionic bonds andπ-stacking interactions,and promote intermolecular overlapping of the triphenylene cores and supramolecular star polymer to tight aggregate.
The study in the fifth part developed a novel strategy for the preparation of ion-bonded supramolecular star polymers by RAFT polymerization.An ion-bonded star supramolecule with six functional groups was prepared by molecular recognition between HDTP and trithiocarbonate carboxylic acid derivative,and used as RAFT agent in polymerization of tert-butylacrylate(tBA) and styrene(St).The obtained polymers were characterized by ~1H NMR and GPC.The results show that the polymerization possesses the characters of living free radical polymerization and the ion-bonded supramolecular star polymers PSt,PtBA,and PSt-b-PtBA with well-defined six-arms have been successfully synthesized.The ion-bonded supramolecular polymer was easily cleaved when the solution pH was changed.
In the last part,a triphenylene(TP)-based six functional initiator was prepared and used for atom transfer radical polymerization of 2-(N,N-dimethylamino)ethyl methacrylate(DMAEMA) and styrene(St).The polymers were characterized by GPC, ~1H NMR and FTIR.The results show that the polymerization possesses the characters of living free radical polymerization,and well-defined six-armed star-shaped block copolymers TP(PDMAEMA-b-PSt)_6 bearing hydrophilic backbones inside and hydrophobic blocks outside were successfully synthesized.The self-assembly behaviors of amphiphilic star block copolymer in selective solvents were investigated by TEM and SEM.Coexisting spherical and bowl-shaped aggregates were observed in neutral aqueous solution,and large spherical structures with different dimension were obtained from self-assembly of the resulting copolymer in diluted HCl and CF_3COOH aqueous solution.The possible mechanism of the morphology formation was suggested.
一、合成了含有六个叔胺基的盘状三亚苯衍生物2,3,6,7,10,11-六(N,N-二甲氨基丙氨基羰基甲氧基)三亚苯(HDTP),将其分别和带有不同数目取代基的苯甲酸衍生物(对十二烷氧基苯甲酸、3,5-二十二烷氧基苯甲酸和3,4,5-三十二烷氧基苯甲酸)作用,合成了六臂,十二臂和十八臂离子键盘状超分子化合物。通过核磁共振氢谱和红外光谱确定了它们的结构。用透射电镜和紫外吸收光谱研究了这些离子键超分子化合物在甲苯溶液中自组装行为。实验结果表明,六臂的盘状超分子化合物能自身组装成片层结构,并使溶剂凝胶化,而十二臂和十八臂盘状超分子化合物在甲苯溶液中聚集成不同长度的纳米纤维,且随着臂数的增多纤维尺寸变短。这是由于过多的烷基链降低超分子化合物的聚集能力,影响了聚集态的形成。
二、用HDTP和对十二烷氧基二联苯甲酸(DBC)作为原料,成功的制备了离子键盘状超分子化合物HDTP/DBC。该超分子化合物能使苯、甲苯、二甲苯等芳烃溶剂形成稳定的凝胶。通过透射电镜和扫描电镜观察到它们在对二甲苯中自组装形成了直径为50到130纳米的纤维聚集体,这些纳米纤维进一步交联形成三维网络结构。对照试验表明,通过DBC组分的长链烷烃的引入有效地增加了超分子化合物在芳烃溶剂中的溶解能力。红外光谱,紫外可见光谱和荧光光谱研究显示,氢键和π-π相互作用是该离子键超分子自组装和凝胶化的主要驱动力。基于实验结果,我们对这种二组分凝胶相结构的形成机理提出了可能性的模型。
三、合成了多官能团衍生物,2,3,6,7,10,11-六(羧酸基甲氧基)三亚苯(HCTP),将它与多官能团三亚苯衍生物HDTP反应,成功地获得了二组分盘状超分子HDTP/HCTP,其结构用红外光谱和核磁氢谱进行了表征。通过紫外可见光谱和荧光光谱的测定说明,三亚苯单元间的π-π堆积作用和盘状分子侧链间的多重离子作用共同促使了两种构筑单元以1:1的摩尔比,面对面地排列形成了维柱状结构聚集体。通过透射电镜观察到了盘状超分子在水溶液中组装形成的三维纤维状聚集结构。
四、采用模板导向组装技术,以三亚苯衍生物HDTP为核和端羧基聚乙二醇(PEG-COOH)作用,成功地合成了六臂离子键盘状超分子星形聚合物HDTP/PEG-COOH。用红外光谱、核磁共振氢谱和凝胶渗透色谱对聚合物的结构进行了表征。通过实验发现,这种超分子聚合物在去离子水、氯仿和甲苯的溶液中能自组装形成球状聚集体,从透射电镜照片上观察到聚集体的尺寸随着溶剂极性的降低而增大。通过荧光光谱的测量发现,荧光强度随着溶剂的极性降低而发生淬灭现象。这与共价键合成的盘状化合物的聚集行为正好相反,说明聚合物中离子键的引入降低了溶质分子与低极性溶剂之间的相互作用,促进了溶质分子自身的聚集。
五、成功地将可逆加成断裂链转移(RAFT)聚合用于离子键超分子星形聚合的制备。首先把三硫代碳酸酯的羧酸衍生物(DMP)与三亚苯衍生物HDTP进行反应,得到了离子键星形超分子链转移剂。在链转移剂的存在下分别进行丙烯酸叔丁酯(tBA)和苯乙烯(St)的RAFT聚合反应,成功地合成出六臂离子键超分子星形聚合物TP(PtBA)_6、TP(PSt)_6、TP(PtBA-b-PSt)_6。聚合物的结构和分子量通过红外光谱、核磁共振氢谱和凝胶渗透色谱进行了表征,结果显示聚合反应具有活性特征,聚合物结构明确,分子量分布较窄(1.02—1.11)。
六、合成了六官能团原子转移自由基聚合(ATRP)引发剂,2,3,6,7,10,11-六(2-溴丙酰基)三亚苯(HBTP),将其用于引发甲基丙烯酸二甲氨基乙酯(DMAEMA)和苯乙烯(St)的聚合,制备了结构明确、分子量分布窄的两亲性星形嵌段聚合物TP(PDMAEMA)_6和TP(PDMAEMA-b-PSt)_6。考察了两亲性星形嵌段共聚物TP(PDMAEMA-b-PSt)_6在溶液中的自组装行为。从电镜照片观察到,在中性水溶液中形成了球和碗状共存的聚集体,这可用粘度控制机理解释。而在稀盐酸溶液中,自组装成了球形反相胶束,这是由于质子化PDMAEMA嵌段能提高超分子在水溶液中的溶解性,有利于较大尺寸反相胶束的形成。不过在三氟乙酸水溶液中,自组装成的球形反相胶束尺寸较小,这是由于三氟甲基的疏水特性所致。
Supramolecular self-assembly is considered to be an efficient strategy to prepare functional materials,in which molecules associate spontaneously into ordered aggregates as a result of noncovalent interactions.The design of materials through self-assembly processes is becoming one of the primary frontiers of supramolecular chemistry.Otherwise,ionic bond is well known as the strongest noncovalent interactions and sensitive to pH.However,so far ionic interactions have largely been neglected in synthesis of supramolecules,especially for ion-bonded supramolecular star polymers,although they have some distinct characteristics,such as fast and facile functionalization,reversibility,self-reparability and environment sensitivity.In this thesis,we designed and synthesized a series of supramolecules by molecular recognition method,which was formed by combining discotic triphenylene derivatives and guest molecules through ionic interaction.Their self-assembly properties in solution were investigated.There are six main parts included in this thesis.
The first part is concentrated on the synthesis a family of discotic supramolecular compounds consisting of 2,3,6,7,10,11-hexakis(N,N-dimethylaminopropylaminocarbonylmethoxy)triphenylene (HDTP) and 4-dodecyloxy-, 3,5-didodecyloxy-,and 3,4,5-tridodecyloxy-benzoic acids via molecular recognition. The structures of resulting products were characterized by Fourier transformation infrared(FTIR) spectra and proton NMR(~1H NMR) spectra.Moreover,their self-assembly behaviors in toluene were investigated by means of transmission electron micrograph(TEM) and UV-vis measurement.Discoctic supramolecular compound with mono-dodecyloxybenzoate units can make solvent gelation and large sheet-like structure was observed,while supramolecular compound with di-and tridodecyloxybenzoate moieties self-assembled into stable nanofibers with different length.It was suggested that the alkyl chains promoted the solubility of supramolecular compound but make against the formation of order aggregates.
The second part shows a novel two-component organgelator.At first,an ion-bonded discotic supramolecular compound was successfully prepared from HDTP and 4'-dodecyloxybiphenyl-4-carboxylic acid(DBC) by ionic self-assembly route.We found that the supramolecular compound can self-assemble into stable gels in aromatic hydrocarbons,such as benzene,toluene,and xylene.Nanofibers with diameters of 50-130 nm were observed in the p-xylene gels by TEM and SEM.The FTIR data in conjunction with UV-vis and fluorescence spectra suggested that the aggregation of the complex into elongated fibers in solution was induced by a directional extended network of hydrogen bonds,π-πinteractions and van der waals force.Based on the experiment analysis,we proposed a tentative self-assembly model of this two-component gel-phase material.
In the third part,we chose two triphenylene-based derivatives with opposite charges,HDTP and 2,3,6,7,10,11-hexakis(carbonylmethoxy)triphenylene(HCTP),to achieve a novel two-component discotic supramolecule by molecular recognition. The structure was checked by FTIR and ~1H NMR.UV-vis together with FL measurement confirmed that the combination of ionic interactions andπ-πinteractions drove two building blocks to construct one-dimensional columnar stacks. TEM image showed a large three-dimensional fibrillar network from aqueous solution,which was composed by the long strands with micrometers in length and approximately 100-160 nm wide.
The forth part describes theπ-conjugated template promoted the formation and self-assembly of well-defined polymer.HDTP was selected as template and combined with PEG-COOH via complementary molecular recognition to provide an ion-bonded discotic supramolecular star polymer HDTP/PEG-COOH.The structure of the resulting polymer was confirmed by ~1H NMR,FTIR and gel permeation chromatography(GPC).The self-assembly behaviors of the supramolecular polymer in deionized water,chloroform,and toluene were investigated.Spherical aggregations were observed by TEM in all solution.Their diameter increases with decrease of the polarity of solvent.UV-vis and fluorescence spectra indicated thatπ-πinteractions between aromatic units play important roles in the formation of aggregates. Fluorescence spectra in different solution further suggest that low polar solvent favorable to enhance more strong ionic bonds andπ-stacking interactions,and promote intermolecular overlapping of the triphenylene cores and supramolecular star polymer to tight aggregate.
The study in the fifth part developed a novel strategy for the preparation of ion-bonded supramolecular star polymers by RAFT polymerization.An ion-bonded star supramolecule with six functional groups was prepared by molecular recognition between HDTP and trithiocarbonate carboxylic acid derivative,and used as RAFT agent in polymerization of tert-butylacrylate(tBA) and styrene(St).The obtained polymers were characterized by ~1H NMR and GPC.The results show that the polymerization possesses the characters of living free radical polymerization and the ion-bonded supramolecular star polymers PSt,PtBA,and PSt-b-PtBA with well-defined six-arms have been successfully synthesized.The ion-bonded supramolecular polymer was easily cleaved when the solution pH was changed.
In the last part,a triphenylene(TP)-based six functional initiator was prepared and used for atom transfer radical polymerization of 2-(N,N-dimethylamino)ethyl methacrylate(DMAEMA) and styrene(St).The polymers were characterized by GPC, ~1H NMR and FTIR.The results show that the polymerization possesses the characters of living free radical polymerization,and well-defined six-armed star-shaped block copolymers TP(PDMAEMA-b-PSt)_6 bearing hydrophilic backbones inside and hydrophobic blocks outside were successfully synthesized.The self-assembly behaviors of amphiphilic star block copolymer in selective solvents were investigated by TEM and SEM.Coexisting spherical and bowl-shaped aggregates were observed in neutral aqueous solution,and large spherical structures with different dimension were obtained from self-assembly of the resulting copolymer in diluted HCl and CF_3COOH aqueous solution.The possible mechanism of the morphology formation was suggested.
引文
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