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Masked Alkyne Equivalents for the Synthesis of Mechanically Interlocked Polyynes **
Author(s) -
Gawel Przemyslaw,
Woltering Steffen L.,
Xiong Yaoyao,
Christensen Kirsten E.,
Anderson Harry L.
Publication year - 2021
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202013623
Subject(s) - catenane , rotaxane , alkyne , chemistry , nanotechnology , photochemistry , combinatorial chemistry , materials science , molecule , organic chemistry , catalysis , supramolecular chemistry
Polyyne polyrotaxanes, encapsulated cyclocarbon catenanes and other fascinating mechanically interlocked carbon‐rich 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. Herein, we report the synthesis of a new bulky MAE based on t ‐butylbicyclo[4.3.1]decatriene. This MAE was used to synthesize a polyyne [2]rotaxane and a masked‐polyyne [3]rotaxane by Cadiot–Chodkiewicz coupling. Glaser cyclo‐oligomerization 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.