摘要
环糊精衍生物及其他大环受体如葫芦脲等的分子识别和组装是当今超分子化学研究的热点领域之一。为了进一步深入研究环糊精衍生物,特别是修饰全甲基化环糊精对于特定客体分子的分子识别机理和组装机制,本文设计合成了一系列化学修饰全甲基化环糊精和全甲基化环糊精包合物并研究其对一些模型客体分子如胆酸,多肽,偶氮苯客体分子的识别能力,另一方面,以全甲基化环糊精,葫芦脲等大环受体和苯胺为起始原料,制备一系列苯胺超分子假聚轮烷,同时采用非共价手段制备具有一定水溶性的碳纳米管,进而开发它们在化学、材料等领域具有应用价值的性能。具体研究内容如下:
(1)设计合成带有萘基团和喹啉基团的全甲基化β-环糊精衍生物,并进一步研究了其对于四种胆酸盐客体的分子键合能力和选择性。利用圆二色光谱、二维核磁、荧光光谱等手段考察了主体化合物对于胆酸盐的分子识别能力。另外,我们还用量热滴定的手段比较了天然β-环糊精和全甲基化β-环糊精对于胆酸客体分子的分子识别行为,并进一步讨论了取代荧光团对于全甲基化β-环糊精衍生物与胆酸分子的包结行为以及由主客体包结引起的光物理/光化学行为。
(2)设计合成了一组萘修饰单β-环糊精和全甲基化β-环糊精,通过圆二色,二维核磁等手段推测了主体分子的构型和包结模式,并通过荧光滴定的方法研究了具有不同形状和性质环糊精空腔的主体分子对于非芳香寡聚二肽和三肽客体分子的键合行为,从而讨论了甲基化对于环糊精空腔在寡聚多肽识别方面的影响。
(3)制备了全甲基化β-环糊精与偶氮苯客体分子4-HAB及4-AAB的包结配合物晶体,通过X-射线衍射,圆二色,二维核磁,等温微量热滴定(ITC)等研究了主客体间的键合及组装行为。系统分析并讨论了配合物的包结模式和键合热力学以便更深入的探讨天然环糊精和全甲基化环糊精的性质。另外,对取代基的差别对于全甲基化环糊精包结络合和聚集行为的影响也进行了讨论。研究发现,和天然β-环糊精相比,全甲基化β-环糊精对于仅取代基不同的偶氮苯客体分子具有明显的区域选择性。
(4)以苯胺和葫芦[7]脲为原料,制备了葫芦[7]脲包裹的苯胺假聚轮烷。利用AFM、TEM、EPR和电化学等手段详细地研究了其形貌和PANI链上阳离子自由基的稳定性。结果表明,和单纯的聚苯胺相比,所得到的葫芦脲假聚轮烷由于主体化合物的包裹,表现出了更好的水溶性和阳离子自由基稳定性。
(5)制备了全甲基化β-环糊精包裹的苯胺假聚轮烷,并进一步研究了该组装体的水溶性和光可控性。全甲基化β-环糊精的引入提高了PANI在水中的溶解度,而且并不会影响PANI链本身的氧化还原性质。另外,该假聚轮烷与螺吡喃的水溶液体系能够通过光照达到控制体系中质子转移的效果。
(6)将全甲基化β-环糊精包裹的苯胺假聚轮烷缠绕到多壁碳纳米管上制备出导电型多壁碳纳米管复合物。该复合物通过了热重分析,拉曼光谱,X-射线光电子能谱,AFM,TEM等一系列手段的表征,水溶性,分散度,稳定性均较单纯多壁碳纳米管有所提高。
The synthesis,molecular recognition and assembly of cyclodextrin and other macrocycle receptors such as cucurbit[n]uril(CB[n]),nanocarbon tube(CNT) et al.are the most popular topics of supramolecular chemistry.To reveal the molecular recognition and assembly mechanisms of cyclodextrins,especially the per-methylated cyclodextrin(PMCD) and their derivatives,we prepared a series of novel per-methylated cyclodextrins and investigated their binding modes and molecular recognition behaviors and assembly arrangements for special guest molecules such as bile slats,oligopeptides and azo benzene derivatives.On the other hand,we successfully acquired two polymeric pseudorotaxanes constructed from CB[7] /PMCD and aniline.Moreover,a water-soluble CNT composite wrapped by PMCD/polyaniline polymeric pseudorotaxane were synthesized.All of these novel assemblies were further employed to explore their properties for the potential applications on chemistry and material fields.The major contents of this thesis are as follows:
(1) Two novel PM-β-CD derivatives(1 and 2) appended with naphthalene and quinoline fluorophores,and further investigated their molecular binding ability and selectivity for bile salts.Complex-induced fluorescent behaviors,binding ability and selectivity for bile salts were checked by using the circular dichroism,2D NMR, steady-state and time-resolved fluorescent spectra.It is our special interest to compare the binding mechanisms betweenβ-CD and PM-β-CD with bile salts,and further discuss that how the substituted fluorescent groups affect the inclusion behaviors of PM-β-CD derivatives,and explore closely their photophysical/photochemical behaviors upon complexation with guests.
(2) Two naphthalene fluorescence moiety linked amino-β-CD derivatives were prepared and their fluorescence behavior and binding mode with six oligopeptides by using fluorescence,circle dichroism and 2D NMR.The experimental results reveal that the different influence on the oligopeptide recognition behavior with different cavity.
(3) Two inclusion complexes of PM-β-CD with 4-HAB and 4-AAB were obtained and their binding and assembly behaviors were studied by means of X-ray crystallography,circular dichroism and 2D NMR spectra,and isothermal titration calorimetry(ITC).To give more deep insight on the respective characteristics of CD and PMCD,their complexation structures and binding thermodynamics were systemically analyzed and discussed.Moreover,it is also our interest to explore how the disparities of substituents of azobenzene guests affect the inclusion complexation and aggregate behavior of PMCD
(4) We constructed a polypseudorotaxane by capsulizing a PANI chain with numerous CB[7]cavities and the sufficient investigation on its morphology and stabilization effect to PANI radical cations by microscopy,EPR and cyclic voltammetry were investigated.
(5) We constructed a polypseudorotaxane by capsulizing a PANI chain with numerous PM-β-CD cavities.The water solubility and photo-modulation controllability were investigated.The introduction of PM-β-CD enhance the water solubility of parent PANI.Moreover,the reversible redox properties of PANI chain remains after the treatment of PM-β-CDs.Furthermore,the proton transfer process of the polypseudorotaxane could be photo-modulated by the spiropyran(SP) even in aqueous solution.
(6) We employed PANI/PM-β-CD polypseudorotaxane to regularly wrap onto the surface of the MWCNT to yield a novel polypseudorotaxane wrapped MWCNT composite.The assembly was characterized by using thermogravimetric analysis,Raman spectroscopy,XPS,TEM and AFM.Moreover,this composite shows an improved solubility and can be stably dispersed in water.
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