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Near‐Infrared Electrochromic Behavior of Dibenzothiepin Derivatives Attached by Two Michler's Hydrol Blue Units

Von Wiley-VCH zur Verfügung gestellt

10,11-Bis[bis(4-dimethylaminophenyl)methylene]dibenzo[ bf ]thiepin ( 1 ) and -oxepin ( 2 ) were prepared as stable yellow crystalline compounds, which are the cyclic analogues of electron-donating hexaarylbutadienes. Upon two-electron oxidation, they are reversibly transformed into the title dications ( 1 2+ and 2 2+ ) exhibiting near-infrared (NIR) absorptions, which were also isolated as stable salts. These redox pairs can serve as new entries into less well-explored organic NIR-electrochromic systems, and the separation of redox peaks (electrochemical bistability) was attained for 1 / 1 2+ and 2 / 2 2+ , thanks to drastic geometrical changes between neutral and dicationic states, as revealed by a series of X-ray analyses. Thiepin- S,S -dioxide analogue ( 3 / 3 2+ ) exhibits quite similar redox behavior due to nonaromatic nature of the dibenzothiepin or -oxepin unit in 1 2+ and 2 2+ , whereas thiepin- S -oxide derivative ( 4 / 4 2+ ) does not exhibit bistability due to the less change in geometry upon electron transfer, showing that a subtle change of a bridging atom in the central seven-membered ring can modify the redox properties.

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