Tetraaminoperylenes: their efficient synthesis and physical properties.

Trimethylsilylation of 1,8-diaminonaphthalene gave 1,8-bis(trimethylsilylamino)naphthalene (1 a), which was in turn lithiated with two molar equivalents of n-butyllithium to give the tris(thf)-solvated dilithium diamide [1,8-[(Me(3)SiN)Li(thf)](2)C(10)H(6)](thf) (2 a). Metal exchange of 2 a with TlCl was carried out in two steps, via the previously characterized mixed-metal amide [1-[(Me(3)SiN)Li(thf)(2)]-8-[(Me(3)SiN)Tl]C(10)H(6)], to give the dithallium diamide [1,8-[(Me(3)SiN)Tl](2)C(10)H(6)] (3 a). Thermolysis of 3 a cleanly gave a 1:1 mixture of the 4,9-bis(trimethylsilylamino)perylenequinone-3,10-bis(trimethylsilylimine) (4 a) and 1 a.