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With The Sites Of Action The Object Of Selection, Design, Synthesis, And Its Self-assembly Of Cucurbituril

Posted on:2009-09-01Degree:MasterType:Thesis
Country:ChinaCandidate:J M YiFull Text:PDF
GTID:2191360248952404Subject:Organic Chemistry
Abstract/Summary:PDF Full Text Request
The poly-functional groups benzimidazoliums(guests) such as 2,2'-Ethylenedibenzimidazolium dichloride(SBE),2,2'-(Butane-1,4-diyl)dibenzimidazolium dichloride(SBB),2,2'-(Hexane-1,6-diyl)-dibenzimidazolium dichloride(SBH),2,2'-(Heptane-1,7-diyl)dibenzimidazolium dichloride(SBHt), 2,2'-(Octane-1,8-diyl)dibenzimidazolium dichloride(SBO),2,2'-(Decane-1,10-diyl)dibenzimidazolium dichloride(SBDE) have been selected,designed and synthesized.The above guests characterized by the method of 1H NMR spectroscopy,MS and single crystal X-ray diffraction determination.We have investigated the interactions of Q[n]and substituted Q[n]with these guests by using 1H NMR spectroscopy,fluorescence spectroscopy and single crystal X-ray diffraction determination.The self-assembly experimental results revealed that the interaction modes depend on the the ratio of Q[n]to guest or the pH of the solution.Firstly,the interaction binding modes of Q[6]and substituted Q[6] depend on the ratio of host to guest,mainly fitted to 1:1 or 2:1 host-guest inclusion complexes. Secondly,combination of results from 1H NMR and the spectrographic methods,one can suggest that two typical interaction modes could exist in the Q[7]-SBE systems,and similar to Q[7]-SBB system, but the titration 1H NMR spectra at different pH for the Q[7]-SBH,Q[7]-SBHt,Q[7]-SBO,Q[7]-SBDE systems gave a different result.At a lower ratio of NQ[7]/Nguest or in acidic medium,the host Q[7] includes the longer bridged alkylene chain of the guest with a simple 1:1 interaction mode,while at higher ratios of Q[7]to guest or in basic medium,a chain shape guest could be borne two Q[7] molecules and form a dumbbell shape inclusion complex.Thirdly,Q[8]-guest system fitted to 1:2 host-guest inclusion complex or 1:1 host-guest supramolecular model.Meanwhile,the crystals of Q[7] @ SBH and substituted Q[7]@ SBH were got for the first time.The result of crystallographic analysis confirmed that the aliphatic chain of protonated SBH is included inside the cavity of Q[7]to form a novel pseudo-rotaxane structure.In addition,we studied the self-assembly of Q[n]with L-amino acids and other guests through X-Ray diffraction structure of crystals,the experimental results revealed that the inclusion complexes of Q[n]with these guests are 1D or multidimensional supramolecular structure.Other researches included that we synthesized a series of 9,10-substitued anthracene derivatives and these compounds maybe contain poly-functional groups,which provided some basic work for further research in investigating host-guest of Q[n]with these organic guests and supramolecular influorescent materials.
Keywords/Search Tags:Cucurbit [n = 6, 7, 8]urils, benzimidazolium, ~1H NMR technique, fluorescence spectroscopy, inclusion complex, X-Ray diffraction, supramolecular chemistry
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