期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 76, 期 9, 页码 3239-3245出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo200139f
关键词
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资金
- National Science Foundation [CHE-0645563, CHE-0749571]
- Robert A. Welch Foundation [F-1621, F-1018]
- Korean WCU [R32-2008-000-10217-0]
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 (38-92%). Depending on their pendant substituents (derived from the azides), the acyclic triazenes exhibited intense absorptions in the visible spectrum (359-428 nm), which were bathochromically shifted by up to Delta lambda = 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-vis spectroelectrochemical experiments revealed that bulk electrolysis may also be used to switch reversibly the colors exhibited by these triazenes.
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