Synthetic Studies on Organic Electric Conductors Containing Heteroatoms

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Novel heteroarenes, naphtho [1,8-bc : 5,4-b'c'] -and Naphtho[1,8-bc : 4,5-b'c'] -dithiophenes (anti-and syn-NDT), isoelectronic with pyrene, were synthesized as new electron donors. Electron donating CT complexes with iodine and DDQ.2,3,6,7-Tetrathiabenzo [1,3-cd : 4,6-c'd'] dipentalene (TBD) was synthesized as a novel electron donor isoelectronic with perylene.TBD has about the same donor ability and formed a relativaly high conductive iodine complex. Various substitution derivatives of 2- (thiopyran-4'-ylidene) -1,3-dithiole and selenium analogues were syuthesized as novel electron donors.Systematic studies on them afforded many highly conductive CT complexes. Pyranylidenemethy1-and thiopyranylidenemethy1-substituted furans, thiophenes, and N-methy1pyrroles were synthesized as precursors of organic metals. Both of the N-methy1pyrroles afforded highly conductive CT complexes with TCNQ.High conductivities of radical cation salts of anthra [1,9-cd : 4,10-c'd'] bis [1,2] dichacogenoles w … More ere studied with their solid structures.2,2'-Bi-and 2,2'5'2"-ter-tellurophenes were prepared as potential components of organic metals. Novel dimeric TTF donors linked with conjugative pi electron spacer were synthesized and their properties were studied. The (E) -ethenylene derivative formed high ly conducting CT complexes with TCNQF_4 and DDQ.2,7-Bis (dicyanomethylene) -2,7-dihydrobenzo- [2,1-b : 3,4-b'] dithiophene and - [1,2-b : 4,3-b'] dithiophene and 2,6-bis (dicyanomethylene) -2,6-dihydrobenzo- [1,2-b : 4,5-b'] dithiophene were synthesized as novel electron acceptors bearing a heteroquinoid system.They behave as good electron acceptors comparable to TCNQ and have a small on-site Coulomb energy in their dianion states. 11,11,12,12-Tetracyano-2,6-anthraquinodimethane (TANT) and its 9,10-derivative s were synthesized. All of them are superior electron acceptors with small on-site Coulomb repulsion in the dianion states. The above acceptors afforded many highly conducting CT complexes with typical electron donors. Less