季氮阳离子与二苯并-24-冠-8构筑的超分子准轮烷
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摘要
基于冠醚特别是二苯并-24-冠-8的分子识别和自组装研究仍是当今超分子化学领域的重要主题之一。为了进一步理解现有识别模式,并更好地应用于构筑超分子建筑,本论文设计合成了一系列季氮阳离子客体化合物,考察了它们与二苯并-24-冠-8(DB24C8)的键合能力,并利用X-单晶衍射研究了它们与DB24C8形成的超分子配合物的晶体结构和固态组装行为。
1.合成了单(双)质子化的4,4′-联吡啶盐,并利用UV-vis、ESI-MS和1H NMR等手段研究了它们与DB24C8的键合行为,测定了主-客体缔合常数。同时,通过X-单晶衍射研究了单质子化4,4′-联吡啶盐与DB24C8形成的配合物的晶体结构和组装行为。
2.合成了五个新的1,2-二(N-酰基氨基吡啶)乙烷衍生物,利用1H NMR和X-单晶衍射等手段研究了端位氨基酰基化对键合DB24C8能力的影响,并采用单点法测定了部分客体与主体的缔合常数。发现端位氨基的酰基化提高了主-客体键合能力以及影响着形成的[2]准轮烷的晶体结构和组装行为。
3.合成了四个新的含酰胺或酰肼基团的1,2-二(吡啶)乙烷衍生物,利用1H NMR和X-单晶衍射等手段研究了这些取代基的引入所产生的影响,发现这些同时具有氢键给体和受体性质的基团显著影响着形成的[2]准轮烷的组装行为。
4.合成了1,2-二(异喹啉)乙烷客体,利用1H NMR和X-单晶衍射等手段研究了稠杂环的引入对键合能力的影响,结果表明与吡啶相连的苯环以并环或取代基的形式存在对键合能力的改变不大。同时,还发现了芳基氧比烷基氧显示出更短的H…O距离这一反常现象。
5.合成了四个端位带吡啶环的二级烷基铵离子客体,利用1H NMR和X-单晶衍射等手段研究了这些客体与DB24C8的键合情况。研究发现吡啶环的引入能够提高二烷基铵离子对DB24C8的键合能力,同时,吡啶环的质子化对形成的准轮烷的晶体结构和组装行为有着非常重要的影响。
Molecular recognition and self-assembly of crwon ether, especially dibenzo-24-crown-8 (DB24C8) has been one of current important topics in supramolecular chemistry. To further deepen understanding of available recognition motifs and to make the best of kown recognition motifs for supramolecular architectures, a series of guests containing positively charged nitrogen center(s) were synthesized and their binding abilities to DB24C8 were investigated. Also, the crystal structures of some complexes with DB24C8 and their self-assemblies in the solid state were explored in detail by X-ray single crystal diffraction.
1. Mono- and diprotonated 4,4′-bipyridine were prepared. And their binding behaviors with DB24C8 were examined by UV-vis absorption spectra, ESI-mass spectra and 1H NMR spectra. Association constants between these two guests and DB24C8 were determined respectively. Furthermore, the complex of monoprotonated 4,4′-bipyridine with DB24C8 was characterized by X-ray diffraction, and its self-assembly in the solid state was investigated.
2. Five novel 1,2-bis(N-acylaminopyridinium)ethane derivatives were prepared. Effects of acylation of the terminal amino groups on the association abilities with DB24C8 were investigated using 1H NMR spectra and X-ray diffraction, and the association constants of some complexes were determined by the single spot method. The results indicated that acylation can enhance their binding abilities and also affects their crystal structures and self-assemblies.
3. Four novel 1,2-bis(pyridinium)ethane derivatives containing acylamide or acylhydrazine groups were synthesized. Effects of the introduction of these groups were explored by means of 1H NMR spectra and X-ray diffraction. The findings showed these groups, which can act as both of hydrogen-bonding donors and receptors, dramatically affected the self-assemblies of [2]pseudorotaxanes between these derivatives and DB24C8.
4. The dication 1,2-bis(isoquinolinium)ethane was prepared. Effect of the incorporation of fused heterocycle on the binding ability was investigated by virtue of 1H NMR spectra and X-ray diffraction. The study suggested that the resulting guests have a similar capability to interact with DB24C8 whether the phenyl group is fused or directly attached as a substituent at the pyridinium ring. Furthermore, an unusual phenomenon that the aryl oxygen atoms exhibit shorter H…O distances than their alkyl counterparts was observed.
5. Four secondary dialkylammonium with a pyridine ring as terminal groups were synthesized. The binding behaviors of these guests to DB24C8 were analyzed based on the 1H NMR spectra and X-ray diffraction. The results revealed that the interaction between the secondary ammonium and DB24C8 was augmented by replacement of phenyl groups with pyridinyl rings and that protonation of terminal pyridine groups essentially affected the crystal structures and completely changed the self-assembly in the solid state.
1.合成了单(双)质子化的4,4′-联吡啶盐,并利用UV-vis、ESI-MS和1H NMR等手段研究了它们与DB24C8的键合行为,测定了主-客体缔合常数。同时,通过X-单晶衍射研究了单质子化4,4′-联吡啶盐与DB24C8形成的配合物的晶体结构和组装行为。
2.合成了五个新的1,2-二(N-酰基氨基吡啶)乙烷衍生物,利用1H NMR和X-单晶衍射等手段研究了端位氨基酰基化对键合DB24C8能力的影响,并采用单点法测定了部分客体与主体的缔合常数。发现端位氨基的酰基化提高了主-客体键合能力以及影响着形成的[2]准轮烷的晶体结构和组装行为。
3.合成了四个新的含酰胺或酰肼基团的1,2-二(吡啶)乙烷衍生物,利用1H NMR和X-单晶衍射等手段研究了这些取代基的引入所产生的影响,发现这些同时具有氢键给体和受体性质的基团显著影响着形成的[2]准轮烷的组装行为。
4.合成了1,2-二(异喹啉)乙烷客体,利用1H NMR和X-单晶衍射等手段研究了稠杂环的引入对键合能力的影响,结果表明与吡啶相连的苯环以并环或取代基的形式存在对键合能力的改变不大。同时,还发现了芳基氧比烷基氧显示出更短的H…O距离这一反常现象。
5.合成了四个端位带吡啶环的二级烷基铵离子客体,利用1H NMR和X-单晶衍射等手段研究了这些客体与DB24C8的键合情况。研究发现吡啶环的引入能够提高二烷基铵离子对DB24C8的键合能力,同时,吡啶环的质子化对形成的准轮烷的晶体结构和组装行为有着非常重要的影响。
Molecular recognition and self-assembly of crwon ether, especially dibenzo-24-crown-8 (DB24C8) has been one of current important topics in supramolecular chemistry. To further deepen understanding of available recognition motifs and to make the best of kown recognition motifs for supramolecular architectures, a series of guests containing positively charged nitrogen center(s) were synthesized and their binding abilities to DB24C8 were investigated. Also, the crystal structures of some complexes with DB24C8 and their self-assemblies in the solid state were explored in detail by X-ray single crystal diffraction.
1. Mono- and diprotonated 4,4′-bipyridine were prepared. And their binding behaviors with DB24C8 were examined by UV-vis absorption spectra, ESI-mass spectra and 1H NMR spectra. Association constants between these two guests and DB24C8 were determined respectively. Furthermore, the complex of monoprotonated 4,4′-bipyridine with DB24C8 was characterized by X-ray diffraction, and its self-assembly in the solid state was investigated.
2. Five novel 1,2-bis(N-acylaminopyridinium)ethane derivatives were prepared. Effects of acylation of the terminal amino groups on the association abilities with DB24C8 were investigated using 1H NMR spectra and X-ray diffraction, and the association constants of some complexes were determined by the single spot method. The results indicated that acylation can enhance their binding abilities and also affects their crystal structures and self-assemblies.
3. Four novel 1,2-bis(pyridinium)ethane derivatives containing acylamide or acylhydrazine groups were synthesized. Effects of the introduction of these groups were explored by means of 1H NMR spectra and X-ray diffraction. The findings showed these groups, which can act as both of hydrogen-bonding donors and receptors, dramatically affected the self-assemblies of [2]pseudorotaxanes between these derivatives and DB24C8.
4. The dication 1,2-bis(isoquinolinium)ethane was prepared. Effect of the incorporation of fused heterocycle on the binding ability was investigated by virtue of 1H NMR spectra and X-ray diffraction. The study suggested that the resulting guests have a similar capability to interact with DB24C8 whether the phenyl group is fused or directly attached as a substituent at the pyridinium ring. Furthermore, an unusual phenomenon that the aryl oxygen atoms exhibit shorter H…O distances than their alkyl counterparts was observed.
5. Four secondary dialkylammonium with a pyridine ring as terminal groups were synthesized. The binding behaviors of these guests to DB24C8 were analyzed based on the 1H NMR spectra and X-ray diffraction. The results revealed that the interaction between the secondary ammonium and DB24C8 was augmented by replacement of phenyl groups with pyridinyl rings and that protonation of terminal pyridine groups essentially affected the crystal structures and completely changed the self-assembly in the solid state.
引文
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