Study On Synthesis Of Calixpyrrole Macrocyclic Compounds

Supramolecular chemistry is an emerging subject in a speedy development. Molecular recognition, which plays an important role in supramolecular chemistry, has been widely used in many fields, such as life science, information science and so on. The molecular recognition is a process that the host (receptor) produces selectively binding and a specific function on the guest (substrate). Thus, calixpyrrole compounds, having a good recognition between anions and neutral molecules, have attracted more and more researchers’ attention.The synthesis of calix[4]pyrrole macrocyclic and indanone compounds is the main object of research in this thesis. Nearly thirty kinds of compounds including eight new compounds were synthesized and studied. Synthetic routes and purification processes were also optimized. This work includes the three aspects below.(1) Synthesis and characterization of meso-tetramethyl-tetrakis-(p-hy-droxyphenyl) calix[4]pyrrole and its derivatives. Meso-tetramethyl-tetrakis-(p-hydroxyphenyl) calix[4]pyrrole and its derivatives were synthesized from the raw material of p-hydroxyacetophenone. Five kinds of macrocyclic calix[4]pyrroles were prepared from esterification reaction of meso-tetramethyl-tetrakis-(p-hydroxyphenyl) calix[4]pyrrole and some acid chlo-ride. Four of them are firstly reported in the paper. The synthetic route and purification process were also optimized. Meanwhile, four kinds of dendrimer compounds including three unreported compounds were synthesized via reactions of meso-tetramethyl-tetrakis-(p-hydroxyphenyl) calix[4]pyrrole with methyl chloroacetate, hydrazine hydrate, ethylene diamine and methyl acrylate. Besides, meso-tetramethyl-tetrakis-(p-hydro-xyphenyl) calix[4]pyrrole could recognize some small molecules such as acetone, acetonitrile and N, N-dimethylformamide in a molar ratio of 2:1,2:1 and 1:1 from 1H NMR spectra. Moreover, dendrimer compound 10 could recognize cobalt ions from tetra (p-isopropylphenyl) cobalt porphyrin from UV-visible spectra.(2) Synthesis and characterization of meso-tetramethyl-tetrakis-(dihy-droxyphenyl) calix[4]pyrroles.3,4-Dihydroxyacetophenone,2,4-dihydroxyl-acetophenone,2,5-dihydroxyacetophenone were firstly prepared in the synthesis of the calix[4]pyrroles. Meso-tetramethyl-tetrakis-(3,4-dihydroxy-phenyl) calix[4]pyrrole with yield of 20.5%is a new compound and its structure was characterized by 1H NMR,13C NMR and elemental analysis.(3) Synthesis and characterization of 1-indanone compounds. A series of 1-indanone compounds based on acrylic acid were obtained by optimizing the synthesis route and purification process. A suitable synthetic route of 1-indanones has been reported.All compounds synthesized in this work were well characterized by 1HNMR,13CNMR, IR and elemental analysis.