The Synthesis of 3, 3'-Diisoviolanthronyl

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  • 3, 3'-ジイソビオラントロニルの合成
  • 3 , 3-ジイソビオラントロニル ノ ゴウセイ
  • 芳香族多環化合物のUllmann反応に関する研究 (第4報)

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3, 3'-Diisoviolanthronyl (6) which is expected to have high electronic semiconductivity was prepared in 90% yield by ring closure of isomeric quarterbenzanthrones (4) and (5) in ethanolic potassium hydoroxide solutions at 120°C.<BR>The dimer of 3, 4'-dibenzanthrone (isoviolanthrone) which has C-C linkage at the 3 positions of both isoviolanthrone nuclei, has electronic conductivity as much as 30 times of its monomer isoviolanthrone. The λ max of uv spectra in 98% sulfuric acid shifted by 20 nm to longer region than its monomer.<BR>Two isomeric quarterbenzanthrones (4) and (5) were synthesized by the Ullmann reaction in pyrene with Cu powder from 9-iodo- (2) and 9'-iodo-4, 3'-dibenzanthronyl (3) respectively (yield of (4) 19%, (5) 24%). The structure of these quarterbenzanthrone (4) or (5) was identified on the bases of elemental analyses, the additivity of their uv and visible spectra to 9, 9'-and 3, 4'-dibenzanthronyl, and the similarity of ir spectra of quarterbenzanthrone (4) and (5) corresponding to their intermediates (2) and (3).<BR>On the other hand, direct iodination of 3, 4'-dibenzanthronyl (1) with periodic acid and iodine gave the mixture of monoiodo derivative of (1) in 38% yield. By-product diiodo derivative of (1) was proved to be identical with those obtained by iodination of (2) or (3).<BR>Therefore it was concluded that those diiodo derivative of (1) have the same structure, not 9, 3'-but 9, 9'-diiodo-3, 4'-dibenzanthronyl (7). This evidence shows that the above mixture of monoiodo-3, 4'-dibenzanthronyl, prepared by direct iodination of (1), is composed only of (2) and (3), and this was supported by ir spectra.

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