NHC‐CAAC Heterodimers with Three Stable Oxidation States |
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Authors: | Dr Dominik Munz Dr Jiaxiang Chu Dr Mohand Melaimi Prof Dr Guy Bertrand |
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Institution: | Joint UCSD-CNRS Research Chemistry Laboratory (UMI 3555), Department of Chemistry and Biochemistry, University of California San Diego, La Jolla, CA, USA |
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Abstract: | The synthesis of N‐heterocyclic carbene (NHC)–cyclic (alkyl)(amino) carbene (CAAC) heterodimers is presented. As the free carbenes do not react together in solution, the synthetic approach involves the addition of a free NHC to a cyclic iminium salt, which results in the formation of the protonated heterodimer. Subsequent deprotonation leads to the isolation of the corresponding mixed Wanzlick dimers. One‐ and two‐electron oxidations of these triazaolefins result in the formation of stable cationic radicals and bis(cations), respectively, which have been isolated and fully characterized. Cyclic voltammetry, UV/Vis spectroscopy, spin density, and DFT calculations suggest that these heterodimers feature complementary electronic properties to tetrathiafulvalenes (TTFs). |
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Keywords: | CAAC electron-rich olefins N-heterocyclic carbenes radical cations tetrathiafulvalenes |
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