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Synthesis and Study of Redox-Active Acyclic Triazenes: Toward Electrochromic Applications
Ono, Robert J.,Suzuki, Yasuo,Khramov, Dimitri M.,Ueda, Mitsuru,Sessler, Jonathan L.,Bielawski, Christopher W. American Chemical Society 2011 Journal of organic chemistry Vol.76 No.9
<P>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 Δλ = 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.</P><P><B>Graphic Abstract</B> <IMG SRC='http://pubs.acs.org/appl/literatum/publisher/achs/journals/content/joceah/2011/joceah.2011.76.issue-9/jo200139f/production/images/medium/jo-2011-00139f_0008.gif'></P><P><A href='http://pubs.acs.org/doi/suppl/10.1021/jo200139f'>ACS Electronic Supporting Info</A></P>