水溶液中的超分子体系性质研究
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摘要
超分子化学的发展经历了冠醚、环糊精、杯芳烃、南瓜尼四代主体化合物。近十年来,主体对客体的分子识别以及分子组装已经成为超分子化学的核心研究内容。南瓜尼类化合物是由甘脲、甲醛在酸性条件下缩合形成的一种具有不同大小空腔的新型环状化合物,疏水性的空腔和两端极性的羰基氧端口是该类分子的共同特征,它们的空腔包合分子或离子的能力尤为突出。我们选择了南瓜尼类化合物中水溶性最好的七元南瓜尼作为主要研究对象,还选择了三种水溶性的间苯二酚杯[4]芳烃磺酸盐类衍生物作为主体分子,通过联苯胺分子以及合成的一系列碳链长短不同的链状客体分子与主体分子在水溶液中相互作用,研究超分子体系在水溶液中的性能,取得了一系列有意义的实验结果:
一、按照文献方法合成了南瓜尼类化合物CB[n](n=5~8)。用联苯胺与之反应,发现这些南瓜尼中,CB[7]对联苯胺的识别作用最好。运用UV-vis和1HNMR谱等方法,确定了CB[7]与联苯胺相互作用的包结比、包结平衡常数等理化参数,并推测了其作用模式。
二、用对氯苯甲醛、间硝基苯甲醛、对硝基苯甲醛、对二甲胺基苯甲醛、对羟基苯甲醛、香兰素分别和1,6-己二胺反应合成了六种长链二元脂肪胺客体(1a~1f)。用对氯苯甲醛、间硝基苯甲醛、对硝基苯甲醛、对二甲胺基苯甲醛、对羟基苯甲醛分别和1,3-丙二胺反应合成了五种短链二元脂肪胺客体(3a~3e)。对这些客体分子进行了紫外吸收光谱、红外光谱、1H NMR等性质表征。利用UV-vis、1H NMR和红外光谱等方法,研究了七元南瓜尼与这些客体分子相互作用的条件,确定了这些主客体配合物的结构特征和包结比、包结平衡常数等理化参数,初步探讨了其作用模式。为南瓜尼在超分子自组装、分子识别、分子捕捉等方面的应用提供有用的信息。
三、以甲基、乙基、苯基桥连间苯二酚杯[4]芳烃母体为原料,合成了对应的间苯二酚杯[4]芳烃磺酸盐类衍生物作为主体分子(MeC,EtC,PhC)。并运用紫外吸收光谱法研究了它们与自制客体在水溶液中的相互作用,初步确定了这些主客体包结物的结构特征和包结比、包结平衡常数等理化参数。
Crownether, cyclodextrin, calixarene and cucurbituri are four macrocyclic compounds of supramolcular chemistry. Cucurbituril is a hexameric macrocyclic compound self-assembled from an acidcatalyzed condensation reaction of glycoluril and formaldehyde, it has the common character of hydrophobic cavity and two portals of polarity carbonylic oxygen atoms. Cucurbit[n]uril has an exceptional capacity to encapsulate other molecules or ions within its cavity. In the past decade host-guest molecular recognition and assembly has become the central research field in supramolecular chemistry. In this article, Cucurbit[7]uril was been chosen as the host which have best solubility in aqueous solution between cucurbiturils. And we synthesized three calix[4]resorcinarene sulfonic acid derivatives as the hosts. Besides, we synthesized six long-chain hexanediamine hydrochlorides (1a~1f) and five short-chain diaminopropane hydrochlorides (3a~3e) as the guests. A series of significant results and developments have been achieved and the main interesting results are as follows:
1. Synthesized cucurbit[n]uril (n=5~8) host compound according to the literature method. Complexation of cucurbit[n]uril and benzidine in the acidic aqueous solution has been studied by using UV spectrum. The recognition effect of the hollow size of cucurbituril for benzidine has been compared, in which CB[7] showed stronger complexation for benzidine, with the depression of the UV absorption of benzidine remarkably. The effect of other cucurbituril is weak. CB[7] is the best choice to recognize benzidine. Complexation of CB[7] with benzidine is investigated thoroughly in the solution system of 0.2mol/L NaCl and 0.1mol/L HCl. According to the experimental results, complexation of CB[7] with benzidine is quite stable. UV spectrum and 1H NMR technique were determined the association constant of CB[7] for benzidine and host-guest complexes’structure characteristic, the ratio of host to guest in complexes, the reaction mechanism and so on.
2. Then six linear aromaticring diamidogen guests (1a~1f)were synthesized by reducing Schiff bases of 4-chlor-benzaldehyde, 3-nitro-benzaldehyde, 4-nitro-benzaldehyde, N,N-dimethylaminobenzaldehyde, 4-hydroxy-benzaldehyde, 4-hydroxyl-3-methoxy-benzaldehyde and 1,6-diaminohexane. The five short-chain diaminopropane hydrochlorides (3a~3e) was synthesized by 4-chlor-benzaldehyde, 3-nitro-benzaldehyde, 4-nitro-benzaldehyde, N,N-dimethylaminobenzaldehyde, 4-hydroxy-benzaldehyde and 1,3-propane diamine. The ultraviolet absorption spectrum, the infrared spectrum and the 1H NMR were used to characterized and investigated the interaction between host and guests, such as the interacted condition, the function pattern, as well as the reaction mechanism. Discussed these host-guest complexes’structure characteristic, the ratio of host to guest in complexes, the equilibrium constants and so on.
3. Tetramethyl, tetraethyl, and tetraphenyl calix[4]resorcinarenes are alkylated with different alkylation reagents to give three functional sulfonic acid derivatives (MeC, EtC, PhC). We investigated host-guest complexes’structure characteristic, the ratio of host to guest in complexes, the equilibrium constants and so on by using the ultraviolet absorption spectrum technique.
一、按照文献方法合成了南瓜尼类化合物CB[n](n=5~8)。用联苯胺与之反应,发现这些南瓜尼中,CB[7]对联苯胺的识别作用最好。运用UV-vis和1HNMR谱等方法,确定了CB[7]与联苯胺相互作用的包结比、包结平衡常数等理化参数,并推测了其作用模式。
二、用对氯苯甲醛、间硝基苯甲醛、对硝基苯甲醛、对二甲胺基苯甲醛、对羟基苯甲醛、香兰素分别和1,6-己二胺反应合成了六种长链二元脂肪胺客体(1a~1f)。用对氯苯甲醛、间硝基苯甲醛、对硝基苯甲醛、对二甲胺基苯甲醛、对羟基苯甲醛分别和1,3-丙二胺反应合成了五种短链二元脂肪胺客体(3a~3e)。对这些客体分子进行了紫外吸收光谱、红外光谱、1H NMR等性质表征。利用UV-vis、1H NMR和红外光谱等方法,研究了七元南瓜尼与这些客体分子相互作用的条件,确定了这些主客体配合物的结构特征和包结比、包结平衡常数等理化参数,初步探讨了其作用模式。为南瓜尼在超分子自组装、分子识别、分子捕捉等方面的应用提供有用的信息。
三、以甲基、乙基、苯基桥连间苯二酚杯[4]芳烃母体为原料,合成了对应的间苯二酚杯[4]芳烃磺酸盐类衍生物作为主体分子(MeC,EtC,PhC)。并运用紫外吸收光谱法研究了它们与自制客体在水溶液中的相互作用,初步确定了这些主客体包结物的结构特征和包结比、包结平衡常数等理化参数。
Crownether, cyclodextrin, calixarene and cucurbituri are four macrocyclic compounds of supramolcular chemistry. Cucurbituril is a hexameric macrocyclic compound self-assembled from an acidcatalyzed condensation reaction of glycoluril and formaldehyde, it has the common character of hydrophobic cavity and two portals of polarity carbonylic oxygen atoms. Cucurbit[n]uril has an exceptional capacity to encapsulate other molecules or ions within its cavity. In the past decade host-guest molecular recognition and assembly has become the central research field in supramolecular chemistry. In this article, Cucurbit[7]uril was been chosen as the host which have best solubility in aqueous solution between cucurbiturils. And we synthesized three calix[4]resorcinarene sulfonic acid derivatives as the hosts. Besides, we synthesized six long-chain hexanediamine hydrochlorides (1a~1f) and five short-chain diaminopropane hydrochlorides (3a~3e) as the guests. A series of significant results and developments have been achieved and the main interesting results are as follows:
1. Synthesized cucurbit[n]uril (n=5~8) host compound according to the literature method. Complexation of cucurbit[n]uril and benzidine in the acidic aqueous solution has been studied by using UV spectrum. The recognition effect of the hollow size of cucurbituril for benzidine has been compared, in which CB[7] showed stronger complexation for benzidine, with the depression of the UV absorption of benzidine remarkably. The effect of other cucurbituril is weak. CB[7] is the best choice to recognize benzidine. Complexation of CB[7] with benzidine is investigated thoroughly in the solution system of 0.2mol/L NaCl and 0.1mol/L HCl. According to the experimental results, complexation of CB[7] with benzidine is quite stable. UV spectrum and 1H NMR technique were determined the association constant of CB[7] for benzidine and host-guest complexes’structure characteristic, the ratio of host to guest in complexes, the reaction mechanism and so on.
2. Then six linear aromaticring diamidogen guests (1a~1f)were synthesized by reducing Schiff bases of 4-chlor-benzaldehyde, 3-nitro-benzaldehyde, 4-nitro-benzaldehyde, N,N-dimethylaminobenzaldehyde, 4-hydroxy-benzaldehyde, 4-hydroxyl-3-methoxy-benzaldehyde and 1,6-diaminohexane. The five short-chain diaminopropane hydrochlorides (3a~3e) was synthesized by 4-chlor-benzaldehyde, 3-nitro-benzaldehyde, 4-nitro-benzaldehyde, N,N-dimethylaminobenzaldehyde, 4-hydroxy-benzaldehyde and 1,3-propane diamine. The ultraviolet absorption spectrum, the infrared spectrum and the 1H NMR were used to characterized and investigated the interaction between host and guests, such as the interacted condition, the function pattern, as well as the reaction mechanism. Discussed these host-guest complexes’structure characteristic, the ratio of host to guest in complexes, the equilibrium constants and so on.
3. Tetramethyl, tetraethyl, and tetraphenyl calix[4]resorcinarenes are alkylated with different alkylation reagents to give three functional sulfonic acid derivatives (MeC, EtC, PhC). We investigated host-guest complexes’structure characteristic, the ratio of host to guest in complexes, the equilibrium constants and so on by using the ultraviolet absorption spectrum technique.
引文
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