Single-wing Extended Tribenzotriquinacenes via Bowl-shaped Dehydrobenzene and Isobenzofuran Tribenzotriquinacene Derivatives

Monoaryne and monoisobenzofuran analogues of a C3v-symmetrical tribenzotriquinacene
(TBTQ)
were generated in situ and trapped with various dienes
and dienophiles, respectively. In this way, a series of single-wing
extended TBTQ derivatives bearing the bowl-shaped TBTQ unit in different
topographical expositions have become accessible. This includes some
novel tribenzotriquinacene “dimers”, in which two TBTQ
bowls are attached in syn- or anti-orientation at the terminal positions of rigid linker units. Several
of these compounds have been characterized by both spectroscopy and
X-ray structural analysis. The efficient access to the TBTQ “dimers”
may lay a useful foundation for further studies of novel container
compounds and supramolecular architectures.