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submitted on 09.10.2020 and posted on 13.10.2020by 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 rotaxane and a maskedpolyyne rotaxane by Cadiot-Chodkiewicz coupling. Glaser cyclooligomerization of the 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