Journal
CHEMICAL SOCIETY REVIEWS
Volume 43, Issue 9, Pages 3184-3203Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c4cs00022f
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Funding
- Deutsche Forschungsgemeinschaft (DFG) [SFB 953]
- FG Cluster of Excellence Engineering of Advanced Materials'' at FAU
- Solar Technologies go Hybrid'' (an initiative of the Bavarian State Ministry for Science, Research and Art)
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Molecules composed of a contiguous sequence of double bonds, the [n] cumulenes, share structural similarities to both of their conjugated relatives, the polyenes and polyynes. The synthesis and properties of [n] cumulenes are, however, quite different from those of either polyenes or polyynes. At an infinite length, [n] cumulenes would provide one structural form of the hypothetical sp-hybridized carbon allotrope carbyne, while shorter derivatives offer model compounds to help to predict the properties of carbyne. Finally, derivatization of the p-electron framework of [n] cumulenes provides a number of different synthetic transformations, with cycloaddition reactions being the most common. In this review, both historical and recent synthetic achievements toward long [n] cumulenes (n >= 5) are discussed. This is followed by a description of our current understanding of the physical and electronic structure of [n] cumulenes based on UV/vis spectroscopy and X-ray crystallography. Finally, the reactivity of long [n] cumulenes is described.
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