新型杯芳烃化合物的合成、识别及几种吸收性树脂的研究
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摘要
以间苯二酚为反应底物,分别与六种芳香醛合成了相应的杯[4]间苯二酚芳烃,并通过红外光谱和氢核磁共振谱对这些化合物进行了表征。其中,用香草醛(4-羟基-3-甲氧基苯甲醛)、异香草醛(3-羟基-4-甲氧基苯甲醛)以及3,4,5-三甲氧基苯甲醛合成的杯[4]间苯二酚芳烃为首次合成。
在2,8,14,20-四对氯苯基杯[4]间苯二酚芳烃37的DMF溶液中,得到了该烃与DMF形成的配合物单晶。测试结果表明,该晶体以C2h构型的椅式构象存在,37分子与DMF分子间的氢键(包括C—H…O与O—H…C弱氢键)作用导致了这一构象的生成。该晶体为片状的三维网络结构,其形成可以被看作是在晶体状态下37分子被DMF“准完全溶剂化(quasi-complete)”的状态。
采用两条路线成功合成了一种在杯[4]芳烃下缘引入α-苯乙胺的酰胺结构的化合物。路线一的方法是以杯芳烃作为起始的反应平台,将分子链分为几个部分依序与之接合,最后用二氯甲烷-甲醇重结晶的方法纯化产物;路线二的方法则是先合成相应的分子链化合物,然后将其一步链接到杯芳烃平台下缘得到目标产物,最后用生成锌配合物中间体的方法纯化。路线一的产率(45.6%)要高出路线二的产率(23.5%)近一倍。
合成了对叔丁基杯[4]芳烃L-苯丙氨酸乙酯Schiff碱以及一种新的杯芳烃二醛和新的杯芳烃二溴化物。并分析研究了作为杯芳烃配合物的客体之一的苦味酸锰的晶体结构。苦味酸根离子为正交晶系,与锰离子没有配位作用。苦味酸根离子没有形成配合物,它们是通过静电和氢键作用力排列在一起的。堆积在一起的苦味酸锰分子中的苯环间存在错位面对面π-π堆积作用。每个苦味酸锰晶胞含有两个水分子结晶。
首次使用钨酸钠作交联剂制备了交联的聚丙烯酸树脂WPAA,并分别用氢氧化钠中和部分树脂得到WPAA-Na以及首次向树脂中引入三乙醇胺得到WPAA-TEA,将上述三种树脂分别进行了红外光谱、热稳定性以及扫描电镜的表征,并将后两种树脂做了吸液性能的测试,结果表明,用钨酸钠交联的聚丙烯酸树脂WPAA-Na和WPAA-TEA有相对较好的吸水和耐盐性能,特别是后者表现出了较高的耐盐性。此外,通过对WPAA-Na的制备与吸水性能的一系列正交实验分析后得出,当单体浓度为45.5%、反应温度为90oC、交联剂浓度为0.4%、引发剂过硫酸钾浓度为1.1%以及中和度为0.85时,树脂的吸水倍率为佳。
首次使用含有多个羟基的大环超分子类化合物杯芳烃和环糊精分别与丙烯酸单体进行交联共聚,同时还引入了醇胺、肌醇和辛醇等含有羟基的小分子。通过对这些聚合物吸收树脂的吸收性能测试发现:对叔丁基杯[4]、[6]、[8]芳烃交联聚合的聚丙烯酸树脂的吸水率和耐盐性各有高低;上述三种树脂对纯的DMF基本无吸收作用,而加入少许水后就有明显吸收;引入上述含有羟基的小分子后的这类树脂的吸液性能与现有的一些高吸收性树脂接近;三种聚丙烯酸酯类树脂对几种有机溶剂的吸收效果大体上与溶剂的极性大小顺序一致。
在制备β-环糊精-聚苯乙烯内含复合物的探索中,我们采用三种方法即水溶剂法、四氢呋喃溶剂法和研磨法进行制备。结果只有在用四氢呋喃溶剂法制备的过程中得到一固体产物,在红外光谱测试结果中被认为同时含有环糊精和聚苯乙烯的结构(具体结构有待进一步确定),其余各产物均为相对纯净的β-环糊精或聚苯乙烯固体。
以聚乙二醇1000为模板成功制备了二氧化硅微球催化剂,使用红外光谱和扫描电镜对其进行了分析和观察。以聚丙烯酸为模板成功制备了钨酸铜多孔微球催化剂,使用高分辨率的场发射透射电镜以及X-射线粉末衍射仪对其进行了形貌的观察和物相的分析。
Six calix[4]recorcinarenes are synthesized by the reaction of resorcin as substrates with six aromatic aldehydes, respectively. These compounds are characterized by IR spectra and 1H NMR spectra. Calix[4]recorcinarenes synthesized with vanillin, isovanillin and 3,4,5-trimethoxy benzaldehyde are first prepared.
Single-crystal of coordination compound 4-chlorobenzaldehyde calix[4]resorcinarene 37-DMF is obtained in solution of 4-chlorobenzaldehyde calix[4]resorcinarene in DMF. The crystal adopts the C2h symmetrical chair conformation. The force of intermolecular hydrogen bonds, including C—H…O and O—H…C, results in the formation of this conformation. The crystal has a sheet structure with three-dimensional network, and can be regarded as“quasi-complete solvation”of 37 by DMF in the crystalline state.
A compound of calix[4]arene,α-phenylethylamine-amides on whose lower rim, are synthesized with two routes. One route is that the groups are connected to calix[4]arene step by step, and the products are purified with recrystallization. The other is that the groups are first synthesized, and then are connected to calix[4]arene by one step. The products are purified with zinc coordination compound as intermediate. Adopting the two routes, the yields are 45.6% and 23.5%, respectively.
The p-tert-butylcalix[4]arenes respectively containing L-phenylane ethyl ester-based Schiff base, aldehyde groups and alkylbromides are synthesised. Hexaaquamanganese(Ⅱ) dipicrate dihydrate is prepared and characterized by single-crystal X-ray diffraction. The anion of picrate is orthorhombic, space group Pccn, and has no coordinative interaction with the manganese metal cation. The picrate anions are uncoordinated, and bound together by electrostatic attraction and hydrogen bonds.They areπ-stacked end to end. There are two lattice water molecules in one unit cell of the compound.
Sodium tungstate was first employed as crosslinker in the preparation to achieve a better cross linked polymer WPAA. Sodium hydroxide and tris(2-hydroxyethyl)amine(TEA) are introduced in the preparation of WPAA-Na and WPAA-TEA hydrogels, respectively. The crosslinked polymers are characterized by IR spectra, thermogravimetetric analysis and scanning electron microscopy. The liquid absorbencies of WPAA-Na and WPAA-TEA are investigated. Results indicate that WPAA-Na and WPAA-TEA show better salt-resistances and water-absorbing rates. Results of a series of orthogonal design methods demonstrate that a crosslinked PAA superabsorbent composite with sodium tungstate, which is synthesized with a composition of 45.5 wt% of monomer, 0.4 wt% of crosslinker, 1.0 wt% of initiator, a neutralization degree of 83%, and a reaction temperature of 90℃, has a good water absorbency.
Supermolecular compounds with several hydroxyl groups, containing calix[4]arenes and cyclodextrins, are first used to crosslinking copolymerize with acrylic monomers. Small molecules with hydroxyl groups, as of alcohol amines, inositols and capryl alcohols, etc. are introduced in the preparation of the crosslinking copolymers. The liquid absorbencies of these copolymers are investigated, and results show that water-absorbing rates and salt-resistances of copolymers with p-tert-butylcalixarenes are different. They show little absorption to DMF, and obvious absorption to mixture of DMF and a dram of water. Small molecules with hydroxyl groups make the liquid absorbencies of these copolymers correspond to those of some present super absorb resins. The rates of absorbing organic solvents by three poacrylic esters are substantially in accord with the order of polarity of these solvents.
Three methods are used to prepare inclusion complexes between cyclodextrins and polystyrene. Only a solid product, which is considered with structure of cyclodextrins and polystyrene by IR spectra, is prepared with THF as solvent. It’s specific structure needs further confirm.
Silicon dioxide microspherical catalyst, which is prepared with polyethylene glycol 1000 as template, is charactered by IR spectra and SEM. Porous copper tungstate microspherical catalyst, which is prepared with polyacrylic acid as template, is charactered by TEM and XRD.
在2,8,14,20-四对氯苯基杯[4]间苯二酚芳烃37的DMF溶液中,得到了该烃与DMF形成的配合物单晶。测试结果表明,该晶体以C2h构型的椅式构象存在,37分子与DMF分子间的氢键(包括C—H…O与O—H…C弱氢键)作用导致了这一构象的生成。该晶体为片状的三维网络结构,其形成可以被看作是在晶体状态下37分子被DMF“准完全溶剂化(quasi-complete)”的状态。
采用两条路线成功合成了一种在杯[4]芳烃下缘引入α-苯乙胺的酰胺结构的化合物。路线一的方法是以杯芳烃作为起始的反应平台,将分子链分为几个部分依序与之接合,最后用二氯甲烷-甲醇重结晶的方法纯化产物;路线二的方法则是先合成相应的分子链化合物,然后将其一步链接到杯芳烃平台下缘得到目标产物,最后用生成锌配合物中间体的方法纯化。路线一的产率(45.6%)要高出路线二的产率(23.5%)近一倍。
合成了对叔丁基杯[4]芳烃L-苯丙氨酸乙酯Schiff碱以及一种新的杯芳烃二醛和新的杯芳烃二溴化物。并分析研究了作为杯芳烃配合物的客体之一的苦味酸锰的晶体结构。苦味酸根离子为正交晶系,与锰离子没有配位作用。苦味酸根离子没有形成配合物,它们是通过静电和氢键作用力排列在一起的。堆积在一起的苦味酸锰分子中的苯环间存在错位面对面π-π堆积作用。每个苦味酸锰晶胞含有两个水分子结晶。
首次使用钨酸钠作交联剂制备了交联的聚丙烯酸树脂WPAA,并分别用氢氧化钠中和部分树脂得到WPAA-Na以及首次向树脂中引入三乙醇胺得到WPAA-TEA,将上述三种树脂分别进行了红外光谱、热稳定性以及扫描电镜的表征,并将后两种树脂做了吸液性能的测试,结果表明,用钨酸钠交联的聚丙烯酸树脂WPAA-Na和WPAA-TEA有相对较好的吸水和耐盐性能,特别是后者表现出了较高的耐盐性。此外,通过对WPAA-Na的制备与吸水性能的一系列正交实验分析后得出,当单体浓度为45.5%、反应温度为90oC、交联剂浓度为0.4%、引发剂过硫酸钾浓度为1.1%以及中和度为0.85时,树脂的吸水倍率为佳。
首次使用含有多个羟基的大环超分子类化合物杯芳烃和环糊精分别与丙烯酸单体进行交联共聚,同时还引入了醇胺、肌醇和辛醇等含有羟基的小分子。通过对这些聚合物吸收树脂的吸收性能测试发现:对叔丁基杯[4]、[6]、[8]芳烃交联聚合的聚丙烯酸树脂的吸水率和耐盐性各有高低;上述三种树脂对纯的DMF基本无吸收作用,而加入少许水后就有明显吸收;引入上述含有羟基的小分子后的这类树脂的吸液性能与现有的一些高吸收性树脂接近;三种聚丙烯酸酯类树脂对几种有机溶剂的吸收效果大体上与溶剂的极性大小顺序一致。
在制备β-环糊精-聚苯乙烯内含复合物的探索中,我们采用三种方法即水溶剂法、四氢呋喃溶剂法和研磨法进行制备。结果只有在用四氢呋喃溶剂法制备的过程中得到一固体产物,在红外光谱测试结果中被认为同时含有环糊精和聚苯乙烯的结构(具体结构有待进一步确定),其余各产物均为相对纯净的β-环糊精或聚苯乙烯固体。
以聚乙二醇1000为模板成功制备了二氧化硅微球催化剂,使用红外光谱和扫描电镜对其进行了分析和观察。以聚丙烯酸为模板成功制备了钨酸铜多孔微球催化剂,使用高分辨率的场发射透射电镜以及X-射线粉末衍射仪对其进行了形貌的观察和物相的分析。
Six calix[4]recorcinarenes are synthesized by the reaction of resorcin as substrates with six aromatic aldehydes, respectively. These compounds are characterized by IR spectra and 1H NMR spectra. Calix[4]recorcinarenes synthesized with vanillin, isovanillin and 3,4,5-trimethoxy benzaldehyde are first prepared.
Single-crystal of coordination compound 4-chlorobenzaldehyde calix[4]resorcinarene 37-DMF is obtained in solution of 4-chlorobenzaldehyde calix[4]resorcinarene in DMF. The crystal adopts the C2h symmetrical chair conformation. The force of intermolecular hydrogen bonds, including C—H…O and O—H…C, results in the formation of this conformation. The crystal has a sheet structure with three-dimensional network, and can be regarded as“quasi-complete solvation”of 37 by DMF in the crystalline state.
A compound of calix[4]arene,α-phenylethylamine-amides on whose lower rim, are synthesized with two routes. One route is that the groups are connected to calix[4]arene step by step, and the products are purified with recrystallization. The other is that the groups are first synthesized, and then are connected to calix[4]arene by one step. The products are purified with zinc coordination compound as intermediate. Adopting the two routes, the yields are 45.6% and 23.5%, respectively.
The p-tert-butylcalix[4]arenes respectively containing L-phenylane ethyl ester-based Schiff base, aldehyde groups and alkylbromides are synthesised. Hexaaquamanganese(Ⅱ) dipicrate dihydrate is prepared and characterized by single-crystal X-ray diffraction. The anion of picrate is orthorhombic, space group Pccn, and has no coordinative interaction with the manganese metal cation. The picrate anions are uncoordinated, and bound together by electrostatic attraction and hydrogen bonds.They areπ-stacked end to end. There are two lattice water molecules in one unit cell of the compound.
Sodium tungstate was first employed as crosslinker in the preparation to achieve a better cross linked polymer WPAA. Sodium hydroxide and tris(2-hydroxyethyl)amine(TEA) are introduced in the preparation of WPAA-Na and WPAA-TEA hydrogels, respectively. The crosslinked polymers are characterized by IR spectra, thermogravimetetric analysis and scanning electron microscopy. The liquid absorbencies of WPAA-Na and WPAA-TEA are investigated. Results indicate that WPAA-Na and WPAA-TEA show better salt-resistances and water-absorbing rates. Results of a series of orthogonal design methods demonstrate that a crosslinked PAA superabsorbent composite with sodium tungstate, which is synthesized with a composition of 45.5 wt% of monomer, 0.4 wt% of crosslinker, 1.0 wt% of initiator, a neutralization degree of 83%, and a reaction temperature of 90℃, has a good water absorbency.
Supermolecular compounds with several hydroxyl groups, containing calix[4]arenes and cyclodextrins, are first used to crosslinking copolymerize with acrylic monomers. Small molecules with hydroxyl groups, as of alcohol amines, inositols and capryl alcohols, etc. are introduced in the preparation of the crosslinking copolymers. The liquid absorbencies of these copolymers are investigated, and results show that water-absorbing rates and salt-resistances of copolymers with p-tert-butylcalixarenes are different. They show little absorption to DMF, and obvious absorption to mixture of DMF and a dram of water. Small molecules with hydroxyl groups make the liquid absorbencies of these copolymers correspond to those of some present super absorb resins. The rates of absorbing organic solvents by three poacrylic esters are substantially in accord with the order of polarity of these solvents.
Three methods are used to prepare inclusion complexes between cyclodextrins and polystyrene. Only a solid product, which is considered with structure of cyclodextrins and polystyrene by IR spectra, is prepared with THF as solvent. It’s specific structure needs further confirm.
Silicon dioxide microspherical catalyst, which is prepared with polyethylene glycol 1000 as template, is charactered by IR spectra and SEM. Porous copper tungstate microspherical catalyst, which is prepared with polyacrylic acid as template, is charactered by TEM and XRD.
引文
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