Tethered 1,4-Benzoquinones and Their DCNQI Derivatives: Syntheses, Electronic Interactions, Redox Properties, Charge-Transfer Complexes, and Copper Salts

✍ Scribed by Siegfried Hünig; Klaus Sinzger; Martina Kemmer; Uwe Langohr; Harald Rieder; Svante Söderholm; Jost-Ulrich von Schütz; Hans-Christoph Wolf

• Publisher: John Wiley and Sons
• Year: 1998
• Tongue: English
• Weight: 570 KB
• Volume: 1998
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/(sici)1099-0690(199809)1998:9<1977::aid-ejoc1977>3.0.co;2-e

✦ Synopsis

Bisquinones 16-20, in which the quinoid moieties are cyclovoltammograms which indicate two independent twostep electron transfers. Similar results arise from ESR tethered by 2-6 methylene units, have been synthesized via the bis(dimethoxybenzenes) 2, 6, 9, 14, and 15. Compounds investigations of the bis(quinone) radical ions. All DCNQIs 21-25 form charge-transfer complexes with TTF and copper 16-20 were transformed into the corresponding bis(DCNQIs) 21-25 using standard procedures. Interactions between the radical anion salts with reasonable powder conductivities.

Since single crystals could not be grown, the structure of two quinoid units, which fade with the length of the tethering chain, have been observed by 13 C-NMR spectroscopy, these materials remains unknown. backed by calculated charge densities (Table ) and by their

FULL PAPER

Scheme 2 Scheme 1 Tether (CH 2 ) 4 pared to mono(DCNQIs). [14] The very low solubilities of 16 prevented isolation of pure 21.