The Synthesis Of Tetrasulfonated Crown Ethers And Its Molecular Binding Behavious In Aqueous Solution

Supramolecular chemistry has been defined as ’the chemistry of the non-covalent bond’, or it can be realized as an subject which illustrates the intermolecular reaction. One of the key goal in supramolecular chemistry is to synthesize and design more efficent macrocyclic receptors with highly affinitive binding towards that specific guests. In this work, we focus our efforts to design new water soluble tetrasulfonated crown ethers, and endow the molecular recognition with a series of guest molecules which are positive charged with-electron deficent structure. The details is as follows:1. The principle of supramolecular chemistry and the binding affinities of different macrocyclic receptors is reviewed.2. Tetrasulfonated-phenylene)-26-crown-8is synthesized, and the molecular binding behavious with N,N’-dimethyl-4,4’-bipyridinium and1,2-bis(pyridinium)ethane are investigated.3. Tetrasulfonated-phenylene)-32-crown-10is synthesized, and its molecular binding behavious with a series organic cations is compared with the one of tetrasulfonated-phenylene)-26-crown-8, showing well-coincided enthalpy-entropy compesation.4. Tetrasulfonated1,5-dinaphtho-32-crown-8and tetrasulfonated1,5-dinaphtho-38-crown-10were synthesized, the molecular binding strength between tetrasulfonated1,5-dinaphtho-32-crown-8N,N’-dimethyl-4,4’-bipyridinium reach up to107M-1in aqueous solution, and the recognition with coenzym NAD+is also performed.5. Molecular binding between tetrasulfonated1,5-dinaphtho-(3n+8)-crown-n (n=8,10) and non-pyridinium guests are investigated, and the selcetive molecular recognition in a four components system is performed.6. The molecular binding between tetrasulfonated1,5-dinaphtho-32-crown-8and tricyclic dyes is investigated, showing the selective recognition with Acridine Orange.