摘要
手性识别是超分子化学领域中的一个重要研究方向。本论文设计合成了一系列刚性酰胺键联双卟啉锌主体分子，并通过圆二色谱、X-射线单晶衍射、紫外可见光谱滴定、核磁氢谱以及DFT/TDDFT量化计算等方法，研究了其对手性客体分子的识别，并探索了刚性酰胺键联金属双卟啉主体分子与手性客体分子手性识别机理。
本论文中，我们以邻氨基苯基卟啉为构建单元，设计合成了四种双酰胺金属卟啉N,N′-二[5-(邻氨基苯基)-10，15，20-三苯基卟啉]草酰胺锌（化合物2）、N,N′-二[5-(邻氨基苯基)-10，15，20-三苯基卟啉]对苯酰胺锌（化合物3）、N,N′-二[5-(邻氨基苯基)-10，15，20-三苯基卟啉]间苯酰胺锌（化合物4）和N,N′-二[5-(邻氨基苯基)-10，15，20-三苯基卟啉]邻苯酰胺锌（化合物5）。利用这四种金属双卟啉为主体分子对五类氨基酸乙酯（D/L-丙氨酸乙酯、D/L-缬氨酸乙酯、D/L-亮氨酸乙酯、D/L-苯丙氨酸乙酯以及D/L-苯甘氨酸乙酯）进行手性识别的研究，发现化合物2、化合物3和化合物4对这五类氨基酸乙酯都具有优越的手性识别性能。
1．以双酰胺金属卟啉N,N′-二[5-(邻氨基苯基)-10，15，20-三苯基卟啉]草酰胺锌（化合物2）为主体，分别对上述五类氨基酸乙酯进行手性识别。圆二色光谱研究表明化合物2与L-型氨基酸乙酯手性识别在Soret带显示正激子手性（excitonchirality），D-型氨基酸乙酯则在Soret带显示负激子手性。我们引入四苯基卟啉锌（[Zn(TPP)]）以及单酰胺金属卟啉5-(邻氨基苯基)-10，15，20-三苯基卟啉]草酰胺甲酯锌（化合物1）作为化合物2参照物，通过紫外光谱滴定测定了其与氨基酸乙酯的键合常数，研究了在主客体识别过程中氢键的作用。通过X-射线单晶衍射以及核磁氢谱研究进一步证实了氢键作用的受体和给体。通过DFT/TDDFT计算，研究L-苯丙氨酸乙酯与化合物2形成的超分子化合物的优化结构，计算得到手性诱导信号与实验相吻合，揭示氨基酸乙酯与化合物2的结合方式，并从分子轨道方面解释了诱导手性信号产生的机理。
2．以N,N′-二[5-(邻氨基苯基)-10，15，20-三苯基卟啉]对苯酰胺锌（化合物3）、N,N′-二[5-(邻氨基苯基)-10，15，20-三苯基卟啉]间苯酰胺锌（化合物4）和N,N′-二[5-(邻氨基苯基)-10，15，20-三苯基卟啉]邻苯酰胺锌（化合物5）为主体，分别对上述五类氨基酸乙酯进行手性诱导。圆二色光谱研究表明化合物3和化合物4对上述五类氨基酸乙酯都具有手性识别信号；与L-型氨基酸酯手性识别在Soret带显示负激子手性，D-型氨基酸酯则在Soret带显示正激子手性，并且化合物4手性识别信号比化合物3手性识别信号强4-5倍。但是，化合物5对上述五类氨基酸乙酯都不具有手性识别性能。通过化合物3和4与氨基酸乙酯紫外可见光谱滴定以及化合物3和4的X-射线单晶衍射研究，探讨了这三种金属双卟啉化合物与氨基酸乙酯手性识别作用的机理。
Chiral recognition is one kind of important molecular recognition insupramolecular chemistry. We have designed and synthesized a series of rigidamide-linked zinc(II) bisporphyrinates. Using them as hosts, we have studied theirchiral recognition abilities for chiral guests by circular dichroism spectra, X-raycrystallography, UV-Vis titration,1H NMR and DFT/TDDFT. The correspondingmechanism has also been probed.
In this thesis, we have designed and synthesized four bisporphyrinates containingdouble amide groups on the basis of mono o-aminophenyl substituted porphyrin,N,N′-Bis[5-(o-phenyl)-10,15,20-triphenylporphyrinato-yl)]oxalic amide zinc(II)(compound2), N,N′-Bis[5-(o-phenyl)-10,15,20-triphenylporphyrinato-yl)] p-phthalicamide zinc(II)(compound3), N,N′-Bis[5-(o-phenyl)-10,15,20-triphenylporphyrinato-yl)] m-phthalic amide zinc(II)(compound4) and N,N′-Bis[5-(o-phenyl)-10,15,20-triphenylporphyrinato-yl)] o-phthalic amide zinc(II)(compound5). We have studiedtheir chiral recognition abilities for D/L-alanine ethyl ester, D/L-vlaine ethyl ester,D/L-leucine ethyl ester, D/L-phenylalanine ethyl ester, D/L-phenylglycine ethyl ester.Compound2,3and4have exhibited strong chiral recognition abilities for amino acidesters.
1. Using compound2as a host, we have studied its chiral recognition ability forfive amino acid esters. The ICD spectra showed the positive exciton chirality forL-amino acid esters and negative exciton chirality for D-amino acid esters in Soret band.Using5-(2-(methyl-N-oxamate)-phenyl)-10,15,20-triphenyl-porphyrin Zinc(II)(compo--und1) and tetraphenylporphyrin Zinc(II)([Zn(TPP)]） as reference compounds, wehave studied the role of hydrogen bonds in the chiral recognition process by the UV-Vistitration. We have further investigated the hydrogen bonding interactions between theporphyrin host and amino acid ester by X-ray crystallography and1H NMR. We havealso done DFT/TDDFT calculations between compound2and L-Phe-OEt, which provide the optimized structure of the host-guest complex. The calculated CD signal isconsistent with the experiment result. The origination of CD signal has been explainedthrough molecular orbital transitions.
2. Using compound3,4and5as hosts, we have studied their chiral recognitionability for five amino acid esters. The ICD spectra of complexes formed betweencompound3/4and amino acid esters showed the negative exciton chirality for L-aminoacid esters and positive exciton chirality for D-amino acid esters in Soret band.However, there was no observable CD signal in the case of compound5. We havefurther investigated the interactions between the compound3/4and amino acid ester byX-ray crystallography and UV-Vis titration. The corresponding chiral recognitionmechanism has also been probed.
引文
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