新型Schiff base化合物的合成、表征及性质研究
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摘要
大环席夫碱配合物由于其独特的光谱、结构以及热力学和动力学稳定性，一直是人们广泛关注和研究的对象，并已在生物化学、医药、配位化学、超分子化学、催化、电化学等方面取得了广泛的应用，使得开展大环席夫碱化合物的合成、结构、性质及其应用研究具有重要意义。
本论文的主要研究工作如下：
一、手性大环席夫碱(Salen)的合成及其性质表征
1、亚甲基桥连具有刚性结构手性大环Salen化合物的合成
(1)外消旋的环己二胺的拆分
按文献方法对外消旋的环己二胺进行手性拆分，得到手性(R，R)-1，2-环己二胺。
(2)5，5′-亚甲基-二水杨醛的制备
以水杨醛为原料按文献方法合成得到5，5′-亚甲基-二水杨醛。
(3)亚甲基桥连手性大环Salen化合物的合成及表征。
以5，5′-亚甲基-二水杨醛和(R，R)-1，2-环己二胺为原料，用直接法合成亚甲基桥连手性大环Salen化合物，通过核磁共振波谱、红外光谱、紫外光谱等手段进行了表征。
2、烷氧链桥连具有柔性结构的新型手性大环Salen的合成
(1)2，4-二羟基苯甲醛的制备
按文献方法由间苯二酚制备2，4-二羟基苯甲醛。
(2)二醛—1，6-二(3′-羟基-4′-甲酰苯氧基)取代烷的制备
以间苯二酚、DMF、三氯氧磷为原料经甲酰化制备2，4-二羟基苯甲醛，再以2，4-二羟基苯甲醛同烷基二溴反应，合成长链二醛：1，6-二(3′-羟基-4′-甲酰苯氧基)取代烷。
(3)模板法合成手性大环Salen化合物
以合成得到的长链二醛和(R，R)-1，2-环己二胺为原料进行缩合反应，用模板法合成了烷氧链桥连的手性大环Salen化合物。
(4)手性大环Salen化合物的谱学性质探讨
通过核磁共振波谱、红外光谱、紫外光谱、质谱等手段进行了表征，同时与亚甲基桥连手性大环Salen化合物的谱学性质进行了对比探讨。
二、新型含羟基功能基大环席夫碱的合成及其性质表征
以合成得到的含羟基功能基二胺、5，5′-亚甲基-二水杨醛及二醛-1，4-二(3′-羟基-4′-甲酰苯氧基)取代烷为原料，分别用Ca~(2+)和Ba~(2+)作模板离子，合成了三种新型含羟基功能基大环席夫碱，利用核磁共振波谱、红外光谱、紫外光谱、质谱等手段进行了结构表征，并对它们之间的谱学性质进行了探讨。
三、新型含羟基功能基链状席夫碱化合物的合成、表征与晶体结构
(1)1，3-二(2-胺基苯氧基)-2-丙醇的合成
利用廉价易得的邻硝基酚、环氧氯丙烷为原料，通过醚化、硝基还原得到一种含羟基功能基二胺化合物-1，3-二(2-胺基苯氧基)-2-丙醇。
(2)含羟基功能基长链二胺化合物-1，3-二(2-胺基苯氧基)-2-丙醇的晶体结构
首次获得1，3-二(2-胺基苯氧基)-2-丙醇的单晶体，并对其晶体结构进行解析。单晶结果显示：该分子两个苯环通过醚链相连成一个非共面的结构，晶体结构中化合物分子通过氢键作用形成层状结构。
(3)含羟基功能基链状席夫碱化合物的合成、表征
以合成得到的1，3-二(2-胺基苯氧基)-2-丙醇和乙酰丙酮反应得到一种新型链状席夫碱化合物，并通过核磁共振波谱、红外光谱、紫外光谱、质谱等手段进行了结构表征。
(4)含羟基功能基链状席夫碱化合物的晶体结构解析
单晶结果表明：该分子内的羟基功能基与相邻分子氢原子存在非典型氢键作用，将分子在a方向联结成螺旋型的非共面S型分子结构，在该分子结构中还发现固态席夫碱化合物中少见的N~+-H…O~-离子型氢键。
四、含羟基二胺化合物与瓜环形成包结配合物的单晶结构解析及主客体作用研究
(1)单晶结构解析
利用X-射线衍射方法研究了客体-长链二胺化合物(1，3-二(2-胺基苯氧基)-2-丙醇)与八员瓜环Q[8]所形成包结配合物的晶体结构。结果表明主客体间形成了1：2的包结配合物，两个客体分子分别从瓜环的两个端口进入瓜环内腔，腔内两个客体分子的苯环之间存在着π-π相互作用。分子间通过氢键作用形成空间网络结构。
(2)二胺化合物与瓜环之间主客体作用研究
利用~1H NMR技术、紫外吸收光谱及荧光光谱方法对主客体间的相互作用进行了考察，所得结果与晶体结构吻合。
Macrocyclic Schiff base complexes attract the people's extensive concern and researches because of its special spectrum, structure, thermodynamics and the dynamics stability, and its application involves to many fields such as biochemistry, medicine, coordination chemistry, supermolecular chemistry, catalysis and electrochemistry, etc. Therefore, it is of great important meaning to study the synthesis, structure, property and its application about macrocyclic Schiff base compound.
This main content is shown as follows:
1. Synthesis and characterization of chiral macrocyclic Schiff base (Salen)
(1). Synthesis of chiral macrocyclic salen compound 4 with framework construction due to the two individual schiff base subunits linked covalently by methylene.a. Resolution of externally compensated diaminocyclohexaneChiral (R, R)-1,2-diaminocyclohexane was prepared from externally compensated 1,2-diaminocyclohexane mixation according to the literature.b. Synthesis of 5,5'-Methylene-bis-salicylaldehyde5,5'-Methylene-bis-salicylaldehyde was synthesized from salicylaldehyde according to the literature.c. Synthesis and characterization of the chiral macrocyclic Salen compound 4Salen 4 was synthesized directly by the reaction of 5,5'-Methylene-bis-salicylalde-hyde and (R, R)-1,2-diaminocyclohexane, and the compound was characterized by ~1HNMR, FT-IR, MS spectra and UV-vis.
(2). Synthesis of chiral macrocyclic salen compound 5 with flexible frame construction due to the two individual Schiff base subunits linked covalently by flexible alkoxy chain.a. Synthesis of 2,4-dihydroxybenzaldehyde2,4-dihydroxybenzaldehyde was prepared from resorcinol according to the literature。b. Synthesis of the dialdehyde-1, 6-bis-(3'-hydroxy-4'-formylphenyloxy)alkane 1,6-bis-(3'-hydroxy-4'-formylphenyloxy)alkane was synthesized by the reaction of 2,4-dihydroxybenzaldehyde and dibromoalkyl in acetone according to the literature.c. Synthesis of the new chiral macrocyclic salen compound 5Salen 5 was synthesized from the above dialdehydes and (R, R)-1,2-diaminocyclo-hexane by using Ba~(2+) as template inons in the mixed solution of methanol and THEd. Spectral properties of the chiral macrocyclic salen compound 5The product obtained was characterized by ~1H NMR, FT-IR, UV-vis, Mass spectra, and the spectral properties of salen 4 and 5 were discussed.
(3). Synthesis, characterization and spectral properties of new macrocyclic schiff bases containing hydroxyl functional group.
New macrocyclic schiff bases containing hydroxyl functional group were synthesized from the hydroxy-bearing diamine compound, 5,5'-Methylene-bis-salicyl- aldehyde and the above dialdhyde by using Ca~(2+), Ba~(2+) as template inons. The product obtained was characterized by ~1H NMR, FT-IR, UV-vis spectroscopy, and Mass spectroscopy, and spectral properties of salen 4 and 5 were discussed.
2. Synthesis, characterization and the crystal structure of new schiff base compounds containing hydroxyl functional group.
(1). Synthesis of 1,3-bis- (2-aminophenoxy)-2-propanol.
The diamine compound containing hydroxyl functional group was synthesized by etherization, reduction of nitro group from o-nitrophenol and epichlorohydrin.
(2). The crystal structure of 1,3-bis(2-aminophenoxy)-2-propanol
The single crystal structure of 1,3-bis(2-aminophenoxy)-2-propanol was obtained firstly and discussed .The crystal structure exhibits a layer formation, and the two phenyl rings linked by ethereal chain form a non-coplanar structure. Layers are formed by the intermolecular hydrogen bonding, and the aryl rings in difference molecules are approximately parallel to each other.
(3). Synthesis, characterization and spectral properties of new schiff base compounds containing hydroxyl functional group.
The hydroxy-bearing Schiff base compound has obtained by the condensation of 1,3-bis-(2-aminophenoxy)-2-propanol and acetylacetone, and characterized by IR, ~1H NMR, MS and X-ray single crystal structural analysis. (4). The crystal structure of the hydroxy-bearing Schiff base compound
The crystal structure data shows that a rare intramolecular ionic hydrogen bonding (N~+-H…O~-) exists in the molecular. The intermolecular non-classical hydrogen bands C-H…O links the Schiff base molecular of non-coplanar S configuration into a helix chain structure along the a axis.
3. Study on the crytal structure and interaction of cucurbituril with the hydroxy-bearing diamine compound.
(1). The structure analysis of the crystal
The crystal structure of the inclusion complex with cucurbituril (Q[8]) and 1,3-bis (2-aminophenoxy)-2-propanol was determined by X-ray diffraction analysis. The results showed that the Q[8] bind guest to form an inclusion complex in a ratios of 1:2, and intermolecularπ-πinterations exist between the phenyl rings of two guest molecules in cavity of Q[8].
(2). The host-guest interaction study between the diamine compound and Cucurbit[8]uril.
The structure and interaction of Q[8] with the guest were investigated by ~1H NMR techniques, UV spectroscopy and fluorescence spectrophotometry respectively, the results are in good agreement with the crystal structure of the host-guest complex.
本论文的主要研究工作如下：
一、手性大环席夫碱(Salen)的合成及其性质表征
1、亚甲基桥连具有刚性结构手性大环Salen化合物的合成
(1)外消旋的环己二胺的拆分
按文献方法对外消旋的环己二胺进行手性拆分，得到手性(R，R)-1，2-环己二胺。
(2)5，5′-亚甲基-二水杨醛的制备
以水杨醛为原料按文献方法合成得到5，5′-亚甲基-二水杨醛。
(3)亚甲基桥连手性大环Salen化合物的合成及表征。
以5，5′-亚甲基-二水杨醛和(R，R)-1，2-环己二胺为原料，用直接法合成亚甲基桥连手性大环Salen化合物，通过核磁共振波谱、红外光谱、紫外光谱等手段进行了表征。
2、烷氧链桥连具有柔性结构的新型手性大环Salen的合成
(1)2，4-二羟基苯甲醛的制备
按文献方法由间苯二酚制备2，4-二羟基苯甲醛。
(2)二醛—1，6-二(3′-羟基-4′-甲酰苯氧基)取代烷的制备
以间苯二酚、DMF、三氯氧磷为原料经甲酰化制备2，4-二羟基苯甲醛，再以2，4-二羟基苯甲醛同烷基二溴反应，合成长链二醛：1，6-二(3′-羟基-4′-甲酰苯氧基)取代烷。
(3)模板法合成手性大环Salen化合物
以合成得到的长链二醛和(R，R)-1，2-环己二胺为原料进行缩合反应，用模板法合成了烷氧链桥连的手性大环Salen化合物。
(4)手性大环Salen化合物的谱学性质探讨
通过核磁共振波谱、红外光谱、紫外光谱、质谱等手段进行了表征，同时与亚甲基桥连手性大环Salen化合物的谱学性质进行了对比探讨。
二、新型含羟基功能基大环席夫碱的合成及其性质表征
以合成得到的含羟基功能基二胺、5，5′-亚甲基-二水杨醛及二醛-1，4-二(3′-羟基-4′-甲酰苯氧基)取代烷为原料，分别用Ca~(2+)和Ba~(2+)作模板离子，合成了三种新型含羟基功能基大环席夫碱，利用核磁共振波谱、红外光谱、紫外光谱、质谱等手段进行了结构表征，并对它们之间的谱学性质进行了探讨。
三、新型含羟基功能基链状席夫碱化合物的合成、表征与晶体结构
(1)1，3-二(2-胺基苯氧基)-2-丙醇的合成
利用廉价易得的邻硝基酚、环氧氯丙烷为原料，通过醚化、硝基还原得到一种含羟基功能基二胺化合物-1，3-二(2-胺基苯氧基)-2-丙醇。
(2)含羟基功能基长链二胺化合物-1，3-二(2-胺基苯氧基)-2-丙醇的晶体结构
首次获得1，3-二(2-胺基苯氧基)-2-丙醇的单晶体，并对其晶体结构进行解析。单晶结果显示：该分子两个苯环通过醚链相连成一个非共面的结构，晶体结构中化合物分子通过氢键作用形成层状结构。
(3)含羟基功能基链状席夫碱化合物的合成、表征
以合成得到的1，3-二(2-胺基苯氧基)-2-丙醇和乙酰丙酮反应得到一种新型链状席夫碱化合物，并通过核磁共振波谱、红外光谱、紫外光谱、质谱等手段进行了结构表征。
(4)含羟基功能基链状席夫碱化合物的晶体结构解析
单晶结果表明：该分子内的羟基功能基与相邻分子氢原子存在非典型氢键作用，将分子在a方向联结成螺旋型的非共面S型分子结构，在该分子结构中还发现固态席夫碱化合物中少见的N~+-H…O~-离子型氢键。
四、含羟基二胺化合物与瓜环形成包结配合物的单晶结构解析及主客体作用研究
(1)单晶结构解析
利用X-射线衍射方法研究了客体-长链二胺化合物(1，3-二(2-胺基苯氧基)-2-丙醇)与八员瓜环Q[8]所形成包结配合物的晶体结构。结果表明主客体间形成了1：2的包结配合物，两个客体分子分别从瓜环的两个端口进入瓜环内腔，腔内两个客体分子的苯环之间存在着π-π相互作用。分子间通过氢键作用形成空间网络结构。
(2)二胺化合物与瓜环之间主客体作用研究
利用~1H NMR技术、紫外吸收光谱及荧光光谱方法对主客体间的相互作用进行了考察，所得结果与晶体结构吻合。
Macrocyclic Schiff base complexes attract the people's extensive concern and researches because of its special spectrum, structure, thermodynamics and the dynamics stability, and its application involves to many fields such as biochemistry, medicine, coordination chemistry, supermolecular chemistry, catalysis and electrochemistry, etc. Therefore, it is of great important meaning to study the synthesis, structure, property and its application about macrocyclic Schiff base compound.
This main content is shown as follows:
1. Synthesis and characterization of chiral macrocyclic Schiff base (Salen)
(1). Synthesis of chiral macrocyclic salen compound 4 with framework construction due to the two individual schiff base subunits linked covalently by methylene.a. Resolution of externally compensated diaminocyclohexaneChiral (R, R)-1,2-diaminocyclohexane was prepared from externally compensated 1,2-diaminocyclohexane mixation according to the literature.b. Synthesis of 5,5'-Methylene-bis-salicylaldehyde5,5'-Methylene-bis-salicylaldehyde was synthesized from salicylaldehyde according to the literature.c. Synthesis and characterization of the chiral macrocyclic Salen compound 4Salen 4 was synthesized directly by the reaction of 5,5'-Methylene-bis-salicylalde-hyde and (R, R)-1,2-diaminocyclohexane, and the compound was characterized by ~1HNMR, FT-IR, MS spectra and UV-vis.
(2). Synthesis of chiral macrocyclic salen compound 5 with flexible frame construction due to the two individual Schiff base subunits linked covalently by flexible alkoxy chain.a. Synthesis of 2,4-dihydroxybenzaldehyde2,4-dihydroxybenzaldehyde was prepared from resorcinol according to the literature。b. Synthesis of the dialdehyde-1, 6-bis-(3'-hydroxy-4'-formylphenyloxy)alkane 1,6-bis-(3'-hydroxy-4'-formylphenyloxy)alkane was synthesized by the reaction of 2,4-dihydroxybenzaldehyde and dibromoalkyl in acetone according to the literature.c. Synthesis of the new chiral macrocyclic salen compound 5Salen 5 was synthesized from the above dialdehydes and (R, R)-1,2-diaminocyclo-hexane by using Ba~(2+) as template inons in the mixed solution of methanol and THEd. Spectral properties of the chiral macrocyclic salen compound 5The product obtained was characterized by ~1H NMR, FT-IR, UV-vis, Mass spectra, and the spectral properties of salen 4 and 5 were discussed.
(3). Synthesis, characterization and spectral properties of new macrocyclic schiff bases containing hydroxyl functional group.
New macrocyclic schiff bases containing hydroxyl functional group were synthesized from the hydroxy-bearing diamine compound, 5,5'-Methylene-bis-salicyl- aldehyde and the above dialdhyde by using Ca~(2+), Ba~(2+) as template inons. The product obtained was characterized by ~1H NMR, FT-IR, UV-vis spectroscopy, and Mass spectroscopy, and spectral properties of salen 4 and 5 were discussed.
2. Synthesis, characterization and the crystal structure of new schiff base compounds containing hydroxyl functional group.
(1). Synthesis of 1,3-bis- (2-aminophenoxy)-2-propanol.
The diamine compound containing hydroxyl functional group was synthesized by etherization, reduction of nitro group from o-nitrophenol and epichlorohydrin.
(2). The crystal structure of 1,3-bis(2-aminophenoxy)-2-propanol
The single crystal structure of 1,3-bis(2-aminophenoxy)-2-propanol was obtained firstly and discussed .The crystal structure exhibits a layer formation, and the two phenyl rings linked by ethereal chain form a non-coplanar structure. Layers are formed by the intermolecular hydrogen bonding, and the aryl rings in difference molecules are approximately parallel to each other.
(3). Synthesis, characterization and spectral properties of new schiff base compounds containing hydroxyl functional group.
The hydroxy-bearing Schiff base compound has obtained by the condensation of 1,3-bis-(2-aminophenoxy)-2-propanol and acetylacetone, and characterized by IR, ~1H NMR, MS and X-ray single crystal structural analysis. (4). The crystal structure of the hydroxy-bearing Schiff base compound
The crystal structure data shows that a rare intramolecular ionic hydrogen bonding (N~+-H…O~-) exists in the molecular. The intermolecular non-classical hydrogen bands C-H…O links the Schiff base molecular of non-coplanar S configuration into a helix chain structure along the a axis.
3. Study on the crytal structure and interaction of cucurbituril with the hydroxy-bearing diamine compound.
(1). The structure analysis of the crystal
The crystal structure of the inclusion complex with cucurbituril (Q[8]) and 1,3-bis (2-aminophenoxy)-2-propanol was determined by X-ray diffraction analysis. The results showed that the Q[8] bind guest to form an inclusion complex in a ratios of 1:2, and intermolecularπ-πinterations exist between the phenyl rings of two guest molecules in cavity of Q[8].
(2). The host-guest interaction study between the diamine compound and Cucurbit[8]uril.
The structure and interaction of Q[8] with the guest were investigated by ~1H NMR techniques, UV spectroscopy and fluorescence spectrophotometry respectively, the results are in good agreement with the crystal structure of the host-guest complex.
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