The Studies Of The Host-guest Interaction Between Naphthalene Surfactants And Cucurbituril

The supramolecular chemistry (host-guest chemistry) is one direction of the chemical research evolution now, the heart content of host-guest chemistry is molecular recognition and weak interactions between the host and guest. In recent years cucurbituril gradually become important subject of the host-guest chemistry. Surfactant is composed of the hydrophilic and the hydrophobic group, and the hydrophobic chain can enter the hydrophobic cavity of the host compound forming important inclusion complexes. It is found that the surfactants can be as important host molecules. The study of the molecule recognition and association behavior between the host componds (cucurbituril) and the new surfactant molecules, will not only help to further reveal the basic characteristics of weak interactions (the role of non-covalent bond) and mechanism, but also establish a foundation for designing or building a functional supermolecule. This thesis is as a part of the project supported by the National Natural Science Foundation of China (No.20703023,20963007), its content of the present work is as follows:Chapter I introduces the structure, properties and the research methods and progress of host-guest molecular recognition of cucurbituril and surfactants, research methods and progress of the computer simulation of the theoretical calculation.Chapter II introduces the synthesis and characterization of naphthalene cationic surfactants. According to the characteristics of interaction between the host and guest, we designed and synthesized a series of three naphthalene surfactants, they are N, N, N-trimethyl-4-(5-(octyloxy) naphthalene-1-yloxy) butan-1-aminium bromide,4-(5-(decyloxy)naphthalen-1-yloxy)-N,N,N-trimethylbutan-l-aminium bromide,4-(5-(dodecyloxy)naphthalen-1-yloxy)-N,N,N-trimethylbutan-1-aminium bromide.Chapter III introduces the study of the association behaviors of cucurbituril[6] and these surfactants by UV、fluorescence spectroscopy and theoretical calculation. The results show that:the surfactants all form inclusion complexes with the cucurbituril[6], the molar ratio is1:1, and the stability constants (≥105) of the inclusion complexes proved that the inclusion complexes are very stable. With the hydrophobic chain length of the surfactant increasing, the stability constant decrease slightly, the stability constant get to10, showing the stronger inclusion ability. Obviously, the hydrophobic interaction should be the driving force of association behaviors.Chapter IV introduces the study of the association behaviors of cucurbituril[7] and these surfactants by UV、fluorescence spectroscopy and theoretical calculation. The results show that:the surfactants all form inclusion complexes with the cucurbituril[7], the molar ratio is1:1, and the stability constants (≥106) of the inclusion complexes proved that the inclusion complexes are very stable. With the hydrophobic chain length of the surfactant increasing, the stability constant change little, the stability constant get to106, showing the stronger inclusion ability.Chapter Ⅴ introduces the study of the association behaviors of cucurbituril[8] and these surfactants by UV、fluorescence spectroscopy and theoretical calculation. The results show that:the surfactants all form inclusion complexes with the cucurbituril[8], the molar ratio is1:1, and the stability constants (≥107) of the inclusion complexes proved that the inclusion complexes are very stable. With the hydrophobic chain length of the surfactant increasing, the stability constant also change little, the stability constant get to107, showing the stronger inclusion ability.Chapter Ⅵ introduces the conclusions and outlook of this thesis.