Chalcogen-containing fused polycyclic organic material and...

C - Chemistry – Metallurgy – 07 – D

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C07D 495/14 (2006.01) C07D 495/22 (2006.01) C07D 517/14 (2006.01) C07D 517/22 (2006.01) C09K 11/06 (2006.01) H05B 33/14 (2006.01) H05B 33/22 (2006.01)

Patent

CA 2558727

A diacetylene derivative was used as a starting material, and was subjected to dilithiation using an organolithium. reagent. The resulting product was allowed to react with an excessive amount of chalcogen (S, Se). Accordingly, an intramolecular cyclization reaction proceeded simultaneously with formation of skeletons of three rings. As a result, a chalcogen-containing fused polycyclic organic material was found to be obtained which has the three rings and a dichalcogenid bond. Further, by subjecting the resulting compound to a dechalcogenation reaction, a heteroacene was found to be obtained in a satisfactory yield. These synthetic techniques have made it possible to synthesize a series of highly planar chalcogen-containing n-electron system materials. Therefore, it is possible to provide (i) a chalcogen-containing fused polycyclic organic material capable of exhibiting excellent charge-transporting properties and (ii) a method for producing the material.

On utilise un dérivé de diacétylène comme substance de départ et soumis à une dilithiation avec un réactif composé d'organolithium. Le produit résultant de la réaction est mis en réaction avec un excès de chalcogénure (soufre ou sélénium), où une cyclisation intramoléculaire a lieu et, simultanément, les squelettes de trois anneaux se forment. On a ainsi obtenu une substance organique polycyclique à anneau fusionné contenant du chalcogénure et ayant une liaison dichalcogénide. On a aussi trouvé que la soumission du composé résultant à une réaction d'élimination de chalcogénure permet d'obtenir de l' hétéroacène en quantité satisfaisante. Ces techniques de synthèse ont rendu possible la synthétisation d'une série de substances de systèmes d'électrons- pi contenant du chalcogénure hautement planaire. Ainsi, on peut fournir une substance organique polycyclique à anneau fusionné contenant du chalcogénure, aux excellentes propriétés de transfert de charge, et un procédé de production de la substance.

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