The Design Of The Functionalized Calixarenes And Pillararenes As Well As Their Application On The Functional Surfaces

Macrocyclic compounds, such as calixarenes,cyclodextrins and pillararenes, have been well studied and play an important role in supramolecular chemistry. They can be flexibly combined with intelligent materials, then change physical and chemical properties of material surface. They have potential application value for the detection of new sensors and chips. Under the background of this research, the main contents in this paper are that macrocyclic molecules with hydrophobic and rich pi electron cavity are modified on the surfaces and recognize guest molecules by contact angle (CA).Firstly, because the cavity of calixarenes can effectively bag small organic molecules such as amino acids, a novel deep cavity of calix[4]arene (L) with piperidine groups as the upper rim was synthesized and modified on a silicon surface via the click reaction (L-SAMs). The [L+Cys] complex could act as a dual-signal responsive switch for Hg2+ by CA on the silicon surface. The interaction mechanism between L and Cys is proposed by fluorescent (FL) and H NMR.Secondly, based on the structural characteristics and properties of the amine, a new deep cavity of calix[4]arene (M) with dimethylamine groups as the upper rim was synthesized and modified on a silicon surface via the click reaction (M-SAMs). A photoreversible switch based on a photoresponsive host-guest system of dimethylamine-calix[4]arene with 4-(phenylazo) benzoic acid (O) was constructed by CA and FL. The interaction model between M and O is analyzed and discussed.Thirdly, according to the structure characteristics of azo benzoic acid, azo benzoic acid was successfully modified on a silicon surface (O-SAMs). A photoreversible gate valve switch based on ?-NH2-cyclodextrin (CD) and O was constructed by CA and FL. The application and interaction model is analyzed by FL kinetics and H NMR.Fourthly, according to the structural features of adipic acid (AA), adipic acid was successfully modified on a silicon surface (AA-SAMs). A pH responsive gate valve switch based on pillar[5]arene (N) with butoxy groups and AA was constructed by CA and FL. The application and interaction model is analyzed by FL kinetics and 1H NMR.