Synthesis and characterisation of some amidino derivatives of the heterocyclic analogues of Benzo-TCNQ

Investigations into the synthesis of heterocyclic analogues of 11,11,12,12- tetracyano-l,4-naphthaquinodimethane have been carried out to create new acceptor compounds for investigation as electron-acceptors in the synthesis of charge-transfer complexes. Many TCNQ charge-transfer complexes exhibit interesting electrical conductor properties. Pyrolysis of a number of tetraalkylammomum salts of 2,2’-(isomdolin-l,3- diylidene)bispropanedmitrile in tnchlorobenzene was attempted. Though successful N-methylation was achieved, this method did not permit the introduction of other alkyl groups. Marmich type reactions of 2,2’-(isoindolin-l,3- diylidene)bispropanedimtrile and its ammonium salt with formaldehyde in the presence of succmimide or N-methylamline were examined but no products were formed. Investigations were conducted into the possibility of generating a Reformatsky-type organozinc reagent for reaction with N-methylphthalimide as a potential route to 2,2’-(2-methylisoindolin-l, 3-diylidene)bispropanedimtrile. Investigation of the reaction of the ammonium salt of 2,2’-(isoindolin-l,3- diyhdene)bispropanedinitrile with a variety of primary and secondary amines was undertaken. This resulted in new amidine derivatives. Cyclic voltammetry measurements of these compounds showed that they were all electrochemically reversible. Possible charge-transfer interactions between N,N,N\NVtetrarnethyl-p-phenylenediarrune and tetrathiafulvalene and some of the amidine derivatives were investigated by UV spectroscopy