Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 22, Pages 6645-6649Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201501810
Keywords
carbynes; cumulenes; dispersion forces; electrochemistry; rotaxanes
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Funding
- University of Erlangen-Nuremberg
- Deutsche Forschungsgemeinschaft (DFG) (Synthetic Carbon Allotropes) [SFB 953]
- Deutsche Forschungsgemeinschaft (DFG) (DFG grant Rotaxane-Protected Polyynes and Cumulenes)
- Oxford University Raffy Manoukian Scholarship
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The stabilization of long [n]cumulenes has traditionally been achieved by placing sterically bulky protecting groups at the termini, which shield the reactive carbon chain from unwanted reactions. Herein, we present an alternative strategy: stabilization through threading the sp-hybridized carbon chain through a phenanthroline-based macrocycle. The result is stable [9]cumulene rotaxanes that enable the study of properties as a function of length for [n]cumulenes in unprecedented detail, including by quantitative UV/Vis spectroscopy, cyclic voltammetry, and differential scanning calorimetry. The experimental results are supported by DFT calculations.
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