1，8-萘酰亚胺类衍生物和思美泰与瓜环相互作用的研究
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摘要
超分子化学是化学研究的一个热门领域,而瓜环(cucurbit[n]urils(n=5-8,10)作为超分子化学中一类新型的主体化合物受到人们越来越多的关注。瓜环结构稳定,具有刚性结构和疏水空腔,在分子识别,生物化学,药物化学,生物催化等方面有良好的应用前景。
本文主要合成4种1,8-萘酰亚胺类衍生物,并通过1HNMR,质谱,荧光光谱和紫外吸收光谱等方法研究了它们与瓜环的相互作用。研究结果表明,瓜环[n](n=7,8)能与1,8-萘酰亚胺类衍生物形成1∶1的包结物。
金属离子在生命科学,环境科学和生物科学中起着至关重要的作用,所以金属离子的检测是目前人们研究的热点。荧光探针法是目前金属离子检测的主要手段之一,本文设计合成了1,8-萘酰亚胺类衍生物作为荧光探针,该探针能识别金属Cu2+, Co2+, Ni2+,并且具有水溶性好,结构简单,灵敏度高,检测时间短等优点。在1,8-萘酰亚胺衍生物中加入Co2+, Ni2+,化合物的荧光发生淬灭,再加入超分子CB[6]后,荧光又恢复到以前,在此过程中超分子CB[6]则扮演了分子开关的角色。而对于金属Cu2+则没有此变化,这表明1,8-萘酰亚胺类衍生物和CB[6]可以实现对金属Cu2+的专一识别。
本文通过1H NMR, COSY, HSQC等方法对思美泰的核磁氢谱进行了全归属,同时利用核磁、紫外吸收光谱法研究了其与CB[7], CB[8]的相互作用。实验结果表明思美泰分别与CB[7], CB[8]形成了1∶1的包结配合物,但包结的位置不相同。研究还发现CB[8]与思美泰两种异构体的包结位点不同。思美泰与CB[7], CB[8]的包结稳定常数在200L/mol-10000L/mol之间,可以为瓜环作潜在的药物缓释剂提供理论基础。
In recent decades, supramolecular chemistry has become a hot field of chemical research. The cucurbit[n]uril family (CB[n] n=5-8,10) of macrocyclic host molecules have received considerable attention. CB[n] has a good application prospect in molecaular recognition, molecular catalysis, biological chemistry, pharmaceutical chemistry and so on.
In this report, four kinds of1,8-naphthalimide derivatives were synthesized.We mainly study on the interaction between1,8-naphthalimide derivatives and cucurbit[n]uril(CB[n] n=7,8) by1H NMR, ESI-MS, UV-vis spectra and Fluorescence spectra. The results show that1,8-naphthalimide derivatives can enter into the cavity to form a host-guest complex with CB[n](n=7,8).
As metal ions play an important role in environmental and biological processes, so the detection of metal ions is recently of signifcant importance. Nowadays, Fluorescence probe is one of the main methods for the detection of metal ions. In this paper, a new1,8-naphthalimide derivative L was designed and synthesized as fluorescent chemosensor, which exhibited high sensitivity, selectivity and real-time monitoring with fast response time. The fluorescent chemosensor L can selectively detect Cu2+and Co2+, Ni2+ions in aqueous solusion. In addition of Cu2+, Co2+and Ni to the water solution of L, the fluorescence of L is quenched. In the presence of the CB[6], the fluorescence intensity restored for Co2+and Ni2+. Whereas, the addition of CB[6] to the solution of L-Cu2+cann't restore the fluorescence intensity. Therefore, L could be used as a fluorescent sensor of Cu2+.
This paper investigated the interaction of Transmetil (SMT) and Cucurbit[n]uril(CB[n], n=7,8) by using1H NMR, COSY, HSQC and UV-Vis spectroscopy. The results show that the Transmetil was trapped into the cavity of CB[n](n=7,8) to form a1:1host-guest complex in which the binding position of CB[n](n=7,8) was different due to the size of their cavity. The banding modes of CB[8] with isomerous SMT are also different. The binding constants of SMT with CB[7] and CB[8] were measured by UV-Vis spectroscopy and found to be 2314L/mol,8000L/mol, indicating that CB[7] and CB[8] could be used as possible slow-released agents.
本文主要合成4种1,8-萘酰亚胺类衍生物,并通过1HNMR,质谱,荧光光谱和紫外吸收光谱等方法研究了它们与瓜环的相互作用。研究结果表明,瓜环[n](n=7,8)能与1,8-萘酰亚胺类衍生物形成1∶1的包结物。
金属离子在生命科学,环境科学和生物科学中起着至关重要的作用,所以金属离子的检测是目前人们研究的热点。荧光探针法是目前金属离子检测的主要手段之一,本文设计合成了1,8-萘酰亚胺类衍生物作为荧光探针,该探针能识别金属Cu2+, Co2+, Ni2+,并且具有水溶性好,结构简单,灵敏度高,检测时间短等优点。在1,8-萘酰亚胺衍生物中加入Co2+, Ni2+,化合物的荧光发生淬灭,再加入超分子CB[6]后,荧光又恢复到以前,在此过程中超分子CB[6]则扮演了分子开关的角色。而对于金属Cu2+则没有此变化,这表明1,8-萘酰亚胺类衍生物和CB[6]可以实现对金属Cu2+的专一识别。
本文通过1H NMR, COSY, HSQC等方法对思美泰的核磁氢谱进行了全归属,同时利用核磁、紫外吸收光谱法研究了其与CB[7], CB[8]的相互作用。实验结果表明思美泰分别与CB[7], CB[8]形成了1∶1的包结配合物,但包结的位置不相同。研究还发现CB[8]与思美泰两种异构体的包结位点不同。思美泰与CB[7], CB[8]的包结稳定常数在200L/mol-10000L/mol之间,可以为瓜环作潜在的药物缓释剂提供理论基础。
In recent decades, supramolecular chemistry has become a hot field of chemical research. The cucurbit[n]uril family (CB[n] n=5-8,10) of macrocyclic host molecules have received considerable attention. CB[n] has a good application prospect in molecaular recognition, molecular catalysis, biological chemistry, pharmaceutical chemistry and so on.
In this report, four kinds of1,8-naphthalimide derivatives were synthesized.We mainly study on the interaction between1,8-naphthalimide derivatives and cucurbit[n]uril(CB[n] n=7,8) by1H NMR, ESI-MS, UV-vis spectra and Fluorescence spectra. The results show that1,8-naphthalimide derivatives can enter into the cavity to form a host-guest complex with CB[n](n=7,8).
As metal ions play an important role in environmental and biological processes, so the detection of metal ions is recently of signifcant importance. Nowadays, Fluorescence probe is one of the main methods for the detection of metal ions. In this paper, a new1,8-naphthalimide derivative L was designed and synthesized as fluorescent chemosensor, which exhibited high sensitivity, selectivity and real-time monitoring with fast response time. The fluorescent chemosensor L can selectively detect Cu2+and Co2+, Ni2+ions in aqueous solusion. In addition of Cu2+, Co2+and Ni to the water solution of L, the fluorescence of L is quenched. In the presence of the CB[6], the fluorescence intensity restored for Co2+and Ni2+. Whereas, the addition of CB[6] to the solution of L-Cu2+cann't restore the fluorescence intensity. Therefore, L could be used as a fluorescent sensor of Cu2+.
This paper investigated the interaction of Transmetil (SMT) and Cucurbit[n]uril(CB[n], n=7,8) by using1H NMR, COSY, HSQC and UV-Vis spectroscopy. The results show that the Transmetil was trapped into the cavity of CB[n](n=7,8) to form a1:1host-guest complex in which the binding position of CB[n](n=7,8) was different due to the size of their cavity. The banding modes of CB[8] with isomerous SMT are also different. The binding constants of SMT with CB[7] and CB[8] were measured by UV-Vis spectroscopy and found to be 2314L/mol,8000L/mol, indicating that CB[7] and CB[8] could be used as possible slow-released agents.
引文
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