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Masked alkynes for synthesis of threaded carbon chains.
Patrick, Connor W; Gao, Yueze; Gupta, Prakhar; Thompson, Amber L; Parker, Anthony W; Anderson, Harry L.
Affiliation
  • Patrick CW; Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Oxford, UK.
  • Gao Y; Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Oxford, UK.
  • Gupta P; Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Oxford, UK.
  • Thompson AL; Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Oxford, UK.
  • Parker AW; Central Laser Facility, Research Complex at Harwell, Rutherford Appleton Laboratory, Didcot, UK.
  • Anderson HL; Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Oxford, UK. harry.anderson@chem.ox.ac.uk.
Nat Chem ; 16(2): 193-200, 2024 Feb.
Article in En | MEDLINE | ID: mdl-37973943
ABSTRACT
Polyynes are chains of sp1 carbon atoms with alternating single and triple bonds. As they become longer, they evolve towards carbyne, the 1D allotrope of carbon, and they become increasingly unstable. It has been anticipated that long polyynes could be stabilized by supramolecular encapsulation, by threading them through macrocycles to form polyrotaxanes-but, until now, polyyne polyrotaxanes with many threaded macrocycles have been synthetically inaccessible. Here we show that masked alkynes, in which the C≡C triple bond is temporarily coordinated to cobalt, can be used to synthesize polyrotaxanes, up to the C68 [5]rotaxane with 34 contiguous triple bonds and four threaded macrocycles. This is the length regime at which the electronic properties of polyynes converge to those of carbyne. Cyclocarbons constitute a related family of molecular carbon allotropes, and cobalt-masked alkynes also provide a route to [3]catenanes and [5]catenanes built around cobalt complexes of cyclo[40]carbon and cyclo[80]carbon, respectively.

Full text: 1 Collection: 01-internacional Database: MEDLINE Language: En Journal: Nat Chem Journal subject: QUIMICA Year: 2024 Document type: Article Affiliation country: United kingdom

Full text: 1 Collection: 01-internacional Database: MEDLINE Language: En Journal: Nat Chem Journal subject: QUIMICA Year: 2024 Document type: Article Affiliation country: United kingdom