Synthesis Of A Novel Isoindoline Cyclophane

Host-guest chemistry is one of the most focused research realms in modern chemistry. Nitrogen heterocylophan is increasingly attracting the scientists' attention because its unique properties. The electron pair in the nitrogen can bind with alkali metal, alkali earth metal and transition. So in the self-assembly chemistry research, Nitrogen heterocyclophan could be the ligands to associate with various metals to assembly supermolecules of special topology and stereo structure Protonized or methylic quaternary ammonium is soluble in water, and it could selectively bind anions of all sorts such as haloids, sulfate, nitrate and even ATP, ADP playing important roles in living system. So it is a kind of organic host for anions.In this dissertation, we introduce the synthesis of a novel isoindoline cyclophane. We proposed the synthetic route and carried it out.Based on literatures, first 1,2,4,5-tetramethylbenzene was brominated by N-bromosuccinimid. The product l,2,4,5-tetrakis(bromomethyl)benzene was added with 1,4-phenylenedimethanamine. We hope they two could produce the expected isoindoline cyclophane. Different solvents such as acetonitrile, methanol, ethanol, and N,N-dimethylformide, etc. were tried, and potassium carbonate, potassium acetate, and triethylamine were experimented as alkali catalysts. Probably due to the topological selectivity, we could not obtain the target molecule.Another synthetic route was proposed. The1,2,4,5-tetrakis(bromomethyl)benzene reacted with p-tolylsulfomamide to 1,2,3,5,6,7-hexahydro-2,6-bis(p-tolylsulfonyl)benzo[1,2-c:4,5-c']-dippyrrole. Then the p-tolylsulonyl group was removed in acidic condition to pruduce the 1,2,3,5,6,7-hexahydro[1,2-c:4,5-c']dipyrrole dihydrobromide. After its reaction with NaOH, the 1,2,3,5,6,7-hexahydro[1,2-c:4,5-c']dipyrrole was obtained. This substrate reacted with m-xylene dibromide in the presence of K₂CO₃ in reflux condition after 48 hours. The target molecule could be gained after further purification.