| Research Abstract |
Here, I report the results of the my project of "the synthesis and properties of a provisionally named Catenacene".
The synthetic strategy for above compound is based upon the diagonal chilation of phenanthroline with copper as frame construction of catenane. Then it was necessary to examine the construction of extened poly acenes containing phenanthrolin moiety. Now the project procceded to the midle point of total synthesis of catenacene.
The reaction of 2,9-dimethyl phenthroline, which prepared by the reaction of phenanthrolin with excess methyl lithium in dry THF repeatedly, with selenium dioxide gave 2,9-diformyl phenanthrolin in good yield. The reaction of it with variety of Wittig reagents gave corresponding prolonged pi-conjugated compounds. However, the McMurry reaction of it gave unidentified compound. The variety of ring formation reaction is now undertaken.
The another route to the catenacene is also examined. That is, the nitration of 1,10-trimethylene-2,9-phenanthrolinedione gave 5,6-dinitro compound, and then it reduced by Sn-HClaq to give 5,6-diamino compound in good yield from starting compound. The condensation of it and the phenanthrolin-5,6-dione under the basic conditions gave phenazine derivative. Treatment of it with POCl_3 gave tetrachloro derivative in good yield as potential intermediate of catenacene. Furthemore, the use of the instrument of the middle pressure chromatogrphy made a facility of isolation of reaction products, and then it gave me a fruiteful results related researches of pi-conjugated compounds. The results of the benefits of the instrument has been appeared in the literatures.
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