Synthesis and Study of Redox-Active Acyclic Triazenes: Toward Electrochromic Applications

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• 作者：Robert J. Ono ; Yasuo Suzuki ; Dimitri M. Khramov ; Mitsuru Ueda ; Jonathan L. Sessler ; Christopher W. Bielawski
• 刊名：Journal of Organic Chemistry
• 出版年：2011
• 出版时间：May 6, 2011
• 年：2011
• 卷：76
• 期：9
• 页码：3239-3245
• 全文大小：889K
• 年卷期：v.76,no.9(May 6, 2011)
• ISSN：1520-6904

文摘

Coupling of various 4-substituted phenyl azides with two distinct quinone-containing N-heterocyclic carbenes (NHCs) afforded the respective mono- and ditopic 1,3-disubstituted acyclic triazenes in moderate to excellent yields (38鈭?2%). Depending on their pendant substituents (derived from the azides), the acyclic triazenes exhibited intense absorptions in the visible spectrum (359鈭?28 nm), which were bathochromically shifted by up to 螖位 = 68 nm upon reduction of the quinone moiety on the component derived from the NHC. Cyclic voltammetry confirmed that the aforementioned redox processes were reversible, and a related set of UV鈭抳is spectroelectrochemical experiments revealed that bulk electrolysis may also be used to switch reversibly the colors exhibited by these triazenes.