缩氨脲基和苄连氮基杯[4]芳烃衍生物的合成与配合性能研究
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摘要
杯芳烃是一类由多个苯酚单元通过亚甲基连接而构成的环状低聚物,被誉为继冠醚和环糊精之后的“第三代超分子主体分子”。杯芳烃易于大量制备,具有独特的三维空腔结构、能包合识别离子和分子客体等特点,近年来在主客体化学领域引起了人们的广泛关注。另外,由于杯芳烃母体的上下缘易于进行多种化学修饰,常被用来作为构筑特定超分子体系的有效分子平台。含杂原子基团修饰的杯芳烃或双杯芳烃衍生物对过渡金属和重金属离子有较好的配合识别能力,并具有独特的光谱特性,在化学分析、离子传感器等领域有着广阔的应用前景。为此,本文设计并合成了多种含氮杂杯[4]芳烃和双杯[4]芳烃衍生物,并研究了它们的客体识别性能和UV光谱性能。
首先,本论文合成了含有席夫碱基和硫脲基的杯[4]芳烃衍生物,并测定了它们对金属阳离子、氨基酸的两相萃取性能,新化合物表现出对软金属离子较好的选择性萃取能力。其次,控制反应条件下,合成并纯化分离了杯[4]单醛衍生物和杯[4]二醛衍生物,然后分别与水合肼发生“2+1”和“2+2”缩合反应制得了两种含有苄连氮单元桥联的双杯[4]芳烃衍生物并研究了双杯[4]芳烃衍生物配合金属离子前后的紫外光谱变化,发现加入软金属离子配合后使双杯[4]芳烃的最大吸收波长发生了不同程度的红移。另外,从杯[4]二醛为原料出发,与水杨醛腙反应制得含苄连氮单元的树枝状杯[4]芳烃衍生物。测定了它们的阳离子萃取性能。最后,本文还设计合成了在杯芳烃的下缘连有双缩氨脲基的分子内桥联新型杯[4]芳烃衍生物,发现这种新主体分子对金属离子和氨基酸均有较好的萃取能力,与精氨酸形成1:1的配合物。
Regarded as "the third supramolecular receptor" along with crown ethers and cyclodetrins,calixarenes are a class of well defined macrocyclic oligomers of phenols bridged by methylene groups.Owing to their unique three-dimensional cavities, convenient preparation in large quantities,versatile complexation and recognization abilities towards ions or molecules;they have received considerable attentions in recent years.Due to easy modification on both lower and upper rims,the parent calixarenes frequently serve as molecular scaffolds for the construction of more elaborate supramolecular systems.Calixarenes or biscalixarenes containing heteroatom groups have good complexation and recognization abilities for transition metal and heavy metal cations.Some of them also have good spectroscopy properties.They can be broadly used in the fields of chemical analysis,ions sensors,etc.In this thesis,the syntheses, characterization,complexation properties,and UV spetra properties of several novel aza-calix[4]arene and benzalazine bis-calix[4]arenes are described in details.
Firstly,a new calix[4]arene derivative with Schiff-base and thiourea units was synthesized.Its extraction properties for metal cations and amino acids were investigated. It possessed good complexation selectivity for soft metal cations.Secondly,calix[4]arene mono-benzaldehyde and di-benzaldehyde derivatives were synthesized under definite reaction conditions.Then they reacted respectively with hydrazine hydrate by "2+1" or "2+2" condensation reaction to obtain two novel benzalazine-bridged bis-calix[4]arenes. Their absorption properties towards metal ions and UV-vis spectra were investigated. Their UV/vis spectra showed a red shift upon the addition of the transition or heavy metal ions.Besides,a dentritic calix[4]arene derivative containing benzalazine groups was also synthesized by reacting calix[4]arene di-benzaldehyde derivatives with salicylide hydrazone.At last,we synthesized a new calix[4]arene derivative bridged by semicarbazone on the lower rims.It was found that this compound exhibited good extraction towards metal ions and amino acids,and formed 1:1 complexation with arginine.
首先,本论文合成了含有席夫碱基和硫脲基的杯[4]芳烃衍生物,并测定了它们对金属阳离子、氨基酸的两相萃取性能,新化合物表现出对软金属离子较好的选择性萃取能力。其次,控制反应条件下,合成并纯化分离了杯[4]单醛衍生物和杯[4]二醛衍生物,然后分别与水合肼发生“2+1”和“2+2”缩合反应制得了两种含有苄连氮单元桥联的双杯[4]芳烃衍生物并研究了双杯[4]芳烃衍生物配合金属离子前后的紫外光谱变化,发现加入软金属离子配合后使双杯[4]芳烃的最大吸收波长发生了不同程度的红移。另外,从杯[4]二醛为原料出发,与水杨醛腙反应制得含苄连氮单元的树枝状杯[4]芳烃衍生物。测定了它们的阳离子萃取性能。最后,本文还设计合成了在杯芳烃的下缘连有双缩氨脲基的分子内桥联新型杯[4]芳烃衍生物,发现这种新主体分子对金属离子和氨基酸均有较好的萃取能力,与精氨酸形成1:1的配合物。
Regarded as "the third supramolecular receptor" along with crown ethers and cyclodetrins,calixarenes are a class of well defined macrocyclic oligomers of phenols bridged by methylene groups.Owing to their unique three-dimensional cavities, convenient preparation in large quantities,versatile complexation and recognization abilities towards ions or molecules;they have received considerable attentions in recent years.Due to easy modification on both lower and upper rims,the parent calixarenes frequently serve as molecular scaffolds for the construction of more elaborate supramolecular systems.Calixarenes or biscalixarenes containing heteroatom groups have good complexation and recognization abilities for transition metal and heavy metal cations.Some of them also have good spectroscopy properties.They can be broadly used in the fields of chemical analysis,ions sensors,etc.In this thesis,the syntheses, characterization,complexation properties,and UV spetra properties of several novel aza-calix[4]arene and benzalazine bis-calix[4]arenes are described in details.
Firstly,a new calix[4]arene derivative with Schiff-base and thiourea units was synthesized.Its extraction properties for metal cations and amino acids were investigated. It possessed good complexation selectivity for soft metal cations.Secondly,calix[4]arene mono-benzaldehyde and di-benzaldehyde derivatives were synthesized under definite reaction conditions.Then they reacted respectively with hydrazine hydrate by "2+1" or "2+2" condensation reaction to obtain two novel benzalazine-bridged bis-calix[4]arenes. Their absorption properties towards metal ions and UV-vis spectra were investigated. Their UV/vis spectra showed a red shift upon the addition of the transition or heavy metal ions.Besides,a dentritic calix[4]arene derivative containing benzalazine groups was also synthesized by reacting calix[4]arene di-benzaldehyde derivatives with salicylide hydrazone.At last,we synthesized a new calix[4]arene derivative bridged by semicarbazone on the lower rims.It was found that this compound exhibited good extraction towards metal ions and amino acids,and formed 1:1 complexation with arginine.
引文
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