基于酰亚胺酸的有机锡（Ⅳ）羧酸酯的合成、表征、晶体结构及其性质研究
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摘要
有机锡羧酸酯结构种类繁多，并被广泛用于催化、热稳定、杀菌、防污及木材防腐等。有机锡羧酸酯的分子及超分子结构和生物活性特别是抗癌活性己经成为当今金属有机配合物研究领域中的热点。然而，对于环状有机锡羧酸酯的结构种类，以及将有机锡羧酸酯应用于主客体分子识别体系的相关研究甚少。
本论文以二丁基氧化锡、三苯基氢氧化锡为底物，设计合成一系列含有杂原子N的酰亚胺酸作为配体，合成了十一个未有文献报道的有机锡羧酸酯。其中包括新型有机锡羧酸酯大环结构，并将其应用于分子识别体系的研究。所有化合物均进行了元素分析、红外光谱和核磁共振谱等测试表征，并用X-射线单晶衍射测得了配合物的晶体结构。研究了具有大环结构的有机锡羧酸酯配合物的固体紫外吸收、热稳定性、荧光性能和抗癌活性。本论文由以下内容组成:
1.利用均苯四甲酸二酐、1,4,5,8-萘四甲酸二酐和甘氨酸反应得到两种配体（H12L和H22L），将配体分别与二正丁基氧化锡反应，得到了矩形盒子状结构的有机锡羧酸酯大环化合物1和2。通过系列表征方法后，对其作为主体，识别芳香类客体小分子的性质进行了深入的研究。荧光测试结果显示化合物1和2具有很强的荧光活性。初步研究了化合物1对三种肿瘤细胞的抑制作用，结果显示1具有良好的抗癌活性。
2.通过3,4,9,10-苝四甲酸二酐和甘氨酸反应，合成配体HL3，将其与二正丁基氧化锡反应，得到了含有9核Sn原子长梯锡氧簇的大环有机锡羧酸酯配合物3。化合物3为单梯大环结构，含有8阶长梯。3具有较高的荧光活性以及良好的抗癌活性。
3.将邻苯二甲酸酐与5-氨基间苯二甲酸合成的配体H42L5,和配体H2L（实验室提供）分别与二正丁基氧化锡反应，得到化合物4和5。化合物4和5为分别具有2核与3核Sn原子的大环。通过热重测试对它们的热稳定性进行了分析，并通过生物活性测试验证两种化合物具有较好的抗癌活性。
4.利用萘酐与甘氨酸、间氨基苯甲酸合成的配体HL6和HL7分别与三苯基氢氧化锡反应，得到两种简单的单体配合物6和7。通过充分表征后，对化合物的多维结构进行了详细分析。使用苯二甲酸酐与对氨基苯甲酸反应得到配体HL8，将HL6和HL8分别与二正丁基氧化锡反应，得到两种单体配合物8和9。化合物8和9为具有轴对称结构的有机锡羧酸酯单体。经过充分表征后，详细分析了化合物的多维结构。
5.利用萘酐与对氨基苯甲酸反应合成配体HL9，将HL7、HL9分别与二正丁基氧化锡反应得到化合物10和11。化合物10和11为具有4核Sn原子的多聚体，其中锡氧骨架呈三阶梯形结构。通过多种测试得到表征后，详细分析了它们的多维结构。
Organotin carboxylates own a wide variety of structures, and they are widely usedin catalysis,thermal stability, sterilization, anti-fouling and wood preservation etc. Themolecular and supramolecular structures oforganotincarboxylates, biological activity,especially anticancer activity of them have become the hotspot of research. However, themacrocyclic structure of organotin carboxylates and their potential ability to selectivelyrecognize, to afford model complex that mimic biological systems is rarely explored.
In this paper, eleven organotin carboxylates were synthesized by the reactions ofdi-n-butyltin oxide andtriphenyltin hydroxide with aromatic imide carboxylic acidligands.Novel organotin macrocyclic structures are included in the synthesizedcomplexes, and applied to the research of molecular recognition system.All the complexeswere characterized by elemental analysis,1H NMR,13C NMR and FT-IR spectroscopy, andthe structures of the complexes were determined by single crystal X-ray diffractionanalysis.The luminescent property and antitumour activities of complexes owningmacrocyclic structure were preliminary studied. And the UV-Vis spectrum and thermalstability were selectively surveyed for some complexes. The dissertation contains thefollowing works:
1. Two amide carboxylate ligands (H2L1/H2L2) were synthesized by the reactions ofpyromellitic dianhydride/1,4,5,8-naphthalenetetracarboxylic dianhydride with glycine.Organotin macrocyclic complexes of rectangular box structure1and2were obtained usingthe ligands to react with di-butyltin oxide respectively. After a series of characterizations, theselective molecular recognition property of them towards aromatic guest molecules werefurther studied. Fluorescence test results showed that complexes1and2have strongfluorescence activity. And a preliminary study of the anti-tumour activity for1to three kindsof tumor cells revealed1has good anticancer activity.
2. H2L3was designed and synthesized by the reaction of3,4,9,10-Perylenetetracarboxylic dianhydride and amino-acetic acid. With the complexationwith di-butyltin oxide, a centrosymmetric macrocycle containing nona-nucleareight-fold-ladder-like organo-oxotin cluster (complex3) was obtained. Complex3showshigh luminescent and antitumour activities.
3. Di-nuclear centrosymmetric dicarboxylate ring (complex4) was synthesized by thereaction of di-butyltin oxide and H2L4(obtained in the lab). Through the reaction of phthalicanhydride with5-aminophthalic acid, we got H2L5. And a trinuclear tricarboxylate macrocycle (complex5) was synthesized by the reaction of di-butyltin oxide with H2L5. Thermal analysessuggest that complexes4and5have good thermally stability. Besides that,4and5show highanti-tumour activity.
4. HL6/HL7was produced by the reaction of benzo[de]isochromene-1,3-dione andglycine/3-aminobenzoic acid. Using them to react with triphenyl stannic hydroxide, we gottwo monomer organotin carboxylates (6and7). After a series of characterizations, themulti-dimensional structures of them are discussed in detail. Ligand HL8was synthesized bythe reaction of phthalic anhydride and p-aminobenzoic acid. Monomers8and9were obtainedby the reactions of di-butyltin oxide with HL6and HL8. Complexes8and9are dibutyltincarboxylates possessing crystallographically imposed two-fold symmetry. After a fullcharacterization, we discussed the multi-dimensional structures of them in detail.
5. Complexes10and11were synthesized by the reactions of di-butyltin oxide withligands HL7andHL9. HL9was obtained by the reaction of naphthaleneanhydride and p-aminobenzoic acid. Complexes10and11are dimeric carboxylatetetraorganodistannoxanes and show a “ladder-like” molecular structure. After a series ofcharacterizations, the multi-dimensional structures of them are discussed in detail.
本论文以二丁基氧化锡、三苯基氢氧化锡为底物，设计合成一系列含有杂原子N的酰亚胺酸作为配体，合成了十一个未有文献报道的有机锡羧酸酯。其中包括新型有机锡羧酸酯大环结构，并将其应用于分子识别体系的研究。所有化合物均进行了元素分析、红外光谱和核磁共振谱等测试表征，并用X-射线单晶衍射测得了配合物的晶体结构。研究了具有大环结构的有机锡羧酸酯配合物的固体紫外吸收、热稳定性、荧光性能和抗癌活性。本论文由以下内容组成:
1.利用均苯四甲酸二酐、1,4,5,8-萘四甲酸二酐和甘氨酸反应得到两种配体（H12L和H22L），将配体分别与二正丁基氧化锡反应，得到了矩形盒子状结构的有机锡羧酸酯大环化合物1和2。通过系列表征方法后，对其作为主体，识别芳香类客体小分子的性质进行了深入的研究。荧光测试结果显示化合物1和2具有很强的荧光活性。初步研究了化合物1对三种肿瘤细胞的抑制作用，结果显示1具有良好的抗癌活性。
2.通过3,4,9,10-苝四甲酸二酐和甘氨酸反应，合成配体HL3，将其与二正丁基氧化锡反应，得到了含有9核Sn原子长梯锡氧簇的大环有机锡羧酸酯配合物3。化合物3为单梯大环结构，含有8阶长梯。3具有较高的荧光活性以及良好的抗癌活性。
3.将邻苯二甲酸酐与5-氨基间苯二甲酸合成的配体H42L5,和配体H2L（实验室提供）分别与二正丁基氧化锡反应，得到化合物4和5。化合物4和5为分别具有2核与3核Sn原子的大环。通过热重测试对它们的热稳定性进行了分析，并通过生物活性测试验证两种化合物具有较好的抗癌活性。
4.利用萘酐与甘氨酸、间氨基苯甲酸合成的配体HL6和HL7分别与三苯基氢氧化锡反应，得到两种简单的单体配合物6和7。通过充分表征后，对化合物的多维结构进行了详细分析。使用苯二甲酸酐与对氨基苯甲酸反应得到配体HL8，将HL6和HL8分别与二正丁基氧化锡反应，得到两种单体配合物8和9。化合物8和9为具有轴对称结构的有机锡羧酸酯单体。经过充分表征后，详细分析了化合物的多维结构。
5.利用萘酐与对氨基苯甲酸反应合成配体HL9，将HL7、HL9分别与二正丁基氧化锡反应得到化合物10和11。化合物10和11为具有4核Sn原子的多聚体，其中锡氧骨架呈三阶梯形结构。通过多种测试得到表征后，详细分析了它们的多维结构。
Organotin carboxylates own a wide variety of structures, and they are widely usedin catalysis,thermal stability, sterilization, anti-fouling and wood preservation etc. Themolecular and supramolecular structures oforganotincarboxylates, biological activity,especially anticancer activity of them have become the hotspot of research. However, themacrocyclic structure of organotin carboxylates and their potential ability to selectivelyrecognize, to afford model complex that mimic biological systems is rarely explored.
In this paper, eleven organotin carboxylates were synthesized by the reactions ofdi-n-butyltin oxide andtriphenyltin hydroxide with aromatic imide carboxylic acidligands.Novel organotin macrocyclic structures are included in the synthesizedcomplexes, and applied to the research of molecular recognition system.All the complexeswere characterized by elemental analysis,1H NMR,13C NMR and FT-IR spectroscopy, andthe structures of the complexes were determined by single crystal X-ray diffractionanalysis.The luminescent property and antitumour activities of complexes owningmacrocyclic structure were preliminary studied. And the UV-Vis spectrum and thermalstability were selectively surveyed for some complexes. The dissertation contains thefollowing works:
1. Two amide carboxylate ligands (H2L1/H2L2) were synthesized by the reactions ofpyromellitic dianhydride/1,4,5,8-naphthalenetetracarboxylic dianhydride with glycine.Organotin macrocyclic complexes of rectangular box structure1and2were obtained usingthe ligands to react with di-butyltin oxide respectively. After a series of characterizations, theselective molecular recognition property of them towards aromatic guest molecules werefurther studied. Fluorescence test results showed that complexes1and2have strongfluorescence activity. And a preliminary study of the anti-tumour activity for1to three kindsof tumor cells revealed1has good anticancer activity.
2. H2L3was designed and synthesized by the reaction of3,4,9,10-Perylenetetracarboxylic dianhydride and amino-acetic acid. With the complexationwith di-butyltin oxide, a centrosymmetric macrocycle containing nona-nucleareight-fold-ladder-like organo-oxotin cluster (complex3) was obtained. Complex3showshigh luminescent and antitumour activities.
3. Di-nuclear centrosymmetric dicarboxylate ring (complex4) was synthesized by thereaction of di-butyltin oxide and H2L4(obtained in the lab). Through the reaction of phthalicanhydride with5-aminophthalic acid, we got H2L5. And a trinuclear tricarboxylate macrocycle (complex5) was synthesized by the reaction of di-butyltin oxide with H2L5. Thermal analysessuggest that complexes4and5have good thermally stability. Besides that,4and5show highanti-tumour activity.
4. HL6/HL7was produced by the reaction of benzo[de]isochromene-1,3-dione andglycine/3-aminobenzoic acid. Using them to react with triphenyl stannic hydroxide, we gottwo monomer organotin carboxylates (6and7). After a series of characterizations, themulti-dimensional structures of them are discussed in detail. Ligand HL8was synthesized bythe reaction of phthalic anhydride and p-aminobenzoic acid. Monomers8and9were obtainedby the reactions of di-butyltin oxide with HL6and HL8. Complexes8and9are dibutyltincarboxylates possessing crystallographically imposed two-fold symmetry. After a fullcharacterization, we discussed the multi-dimensional structures of them in detail.
5. Complexes10and11were synthesized by the reactions of di-butyltin oxide withligands HL7andHL9. HL9was obtained by the reaction of naphthaleneanhydride and p-aminobenzoic acid. Complexes10and11are dimeric carboxylatetetraorganodistannoxanes and show a “ladder-like” molecular structure. After a series ofcharacterizations, the multi-dimensional structures of them are discussed in detail.
引文
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