The Studies Of The Synthesis Of A Series Of Naphthalene Cationic Surfactants And Host-Guest Inclusion Behaviors

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 cyclodextrin and cucurbituril gradually become important subjects 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 or cyclodextrin) 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 wort is as follows:Chapter I introduces the structure, properties and the research methods and progress of host-guest molecular recognition of cyclodextrin, cucurbituril and surfactants.Chapter II introduces the synthesis and characterization of naphthalene cationic surfactants and cucurbituril[8]. 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-1-aminium bromide, 4-(5-(dodecyloxy)naphthalen-1-yloxy)-N,N,N-trimethylbutan-1-aminium bromide, and synthesized CB[8]by hydrothermal method.Chapter III introduces the determination of critical micelle concentration (CMC) for the naphthalene cationic surfactants.Chapter IV introduces the study of the association behaviors ofβ-cyclodextrin and these surfactants by UV, fluorescence,1H NMR spectroscopy and thermal analysis. The results show that:the surfactants all form inclusion complexes with theβ-cyclodextrin, the molar ratio is 1:1, and the stability constants (≥104) of the inclusion complexes proved that the inclusion complexes are very stable, which has also been confirmed by the results of the thermal analysis. With the hydrophobic chain length of the surfactant increasing, the stability constant also increases, showed that inclusion complexes is more stable.Chapter V introduces the study of the association behaviors of cucurbituril[8] and these surfactants by UV and fluorescence spectroscopy. The results show that: the surfactants all form inclusion complexes with the cucurbituril[8], the molar ratio is 1:1, and the stability constants (≥10') 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 increases, compared toβ-CD, the stability constant get to 101, showing the stronger inclusion ability. Obviously, the hydrophobic interaction should be the driving force of association behaviors.Chapter VI introduces the conclusions and outlook of this thesis.