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Masked Alkyne Equivalents for the Synthesis of Mechanically Interlocked Polyynes

preprint
submitted on 09.10.2020 and posted on 13.10.2020 by Przemyslaw Gawel, Steffen Woltering, Yaoyao Xiong, Kirsten Christensen, Harry Anderson
Polyyne polyrotaxanes, encapsulated cyclocarbon catenanes and other fascinating mechanically interlocked carbonrich architectures should become accessible if masked alkyne equivalents (MAEs) can be developed that are large enough to prevent unthreading of a macrocycle, and that can be cleanly unmasked under mild conditions. Here we report the synthesis of a new bulky MAE based on a t-butylbicyclo[4.3.1]decatriene. This MAE was used to synthesize a polyyne [2]rotaxane and a maskedpolyyne [3]rotaxane by Cadiot-Chodkiewicz coupling. Glaser cyclooligomerization of the [2]rotaxane gave masked cyclocarbon catenanes. The unmasking behavior of the catenanes and rotaxanes was tested by photolysis at a range of UV wavelengths. Photochemical unmasking did not proceed cleanly enough to prepare extended encapsulated polyyne polyrotaxanes. We highlight the scope and challenges involved with this approach to interlocked carbon-rich architectures.

Funding

Leverhulme Trust project grant RPG-2017-032

History

Email Address of Submitting Author

harry.anderson@chem.ox.ac.uk

Institution

University of Oxford

Country

UK

ORCID For Submitting Author

0000-0002-1801-8132

Declaration of Conflict of Interest

there is no conflict of interest

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