N. Martin et al., SYNTHESIS OF NOVEL CHLOROSUBSTITUTED N,N-'-DICYANOQUINONEDIIMINES - FORMATION OF CHARGE-TRANSFER COMPLEXES AND COPPER RADICAL-ANION SALTS, Synthetic metals, 64(1), 1994, pp. 83-89
Novel chloro-substituted N,N'-dicyanoquinonediimines (DCNQIs) (5) have
been synthesized from the corresponding quinones (4) by reaction with
bis(trimethylsilyl)carbodiimide (BTC) and titanium tetrachloride. Cyc
lic voltammetry (CV) measurements of the prepared DCNQIs (5) exhibited
the presence of two one-electron reversible reduction waves to the co
rresponding radical anion and dianion. The first reduction potential r
evealed a better acceptor ability of compounds 5 than the parent DCNQI
, these values being strongly dependent on the presence of chlorine at
oms. The H-1 NMR high resolution spectral data showed, when possible,
the presence of the syn-anti isomers in these compounds (5). Charge tr
ansfer complexes (6) of the novel DCNQIs (5) with the donor tetrathiaf
ulvalene (TTF) and also the copper radical-anion salts (7) have been o
btained. Room temperature conductivities of the charge transfer comple
xes (6) and charge transfer salts (7) were measured and the temperatur
e dependence exhibited a semiconducting behaviour.