Studies On The Synthesis Of Biomimetic Compounds Tetraazaparacyclophane Derivatives

Cyclophane chemistry is an exciting and rapidly growing field of organic chemistry in the recent decades. The appearance of cyclophane compounds arouse the enthusiasm of chemists to research them widely. Tetrazacyclophanes are important compounds of cyclophanes, and also are important host compounds in host-guest chemistry.From the structure, tetraazaparacyclophane is a ring compound with benzene rings connected by nitrogen-containing carbon bridges. It has a well-defined hydrophobic cavity. In addition, the benzene rings are fixed at an angle and "face" conformation, which enables the formation of an inclusion cavity. As an artificial enzyme, it can be optimized by changing the diphenylmethane units or bridging chains or by chemical modification of hydrophobic cavities to form new host compounds. Different host compounds can recognize different guest compounds to become an supramolecular system. It can complex catalyze different reaction substance to control reaction selectively and increase the reaction speed. So the enzyme simulation and molecular recognition can be realized.Nine compounds were synthesized by high-dilution method, and six compounds are new. The reported synthesis method was improved in this thesis. Tetraazacyclophanes were modified by using ferrocenoyl chloride, so a new kind of enzyme model was obtained by introducing the active group. The structures of all the compounds were approved by 1H NMR 13C NMR IR, elemental analysis and MS.In addition the stereo structures of tetraazacyclophanes were computed by Gaussian 98 procedure and AMI method. Parameters such as the lengths and angles of bonds and electric charge distributing were obtained by computing. It will give directions to the studying on the molecular recognition of tetraazacyclophanes.Yuchan Su (Organic Chemistry) Directed by Shi Zhen...