ja6b09011_si_001.pdf (2.16 MB)
Mechanochemical Synthesis of Extended Iptycenes
journal contribution
posted on 2016-10-14, 14:03 authored by Yanchuan Zhao, Silvia V. Rocha, Timothy M. SwagerIptycenes are intriguing compounds
receiving considerable attention
as a result of their rigid noncompliant three-dimensional architecture.
The preparation of larger iptycenes is often problematic, as a result
of their limited solubility and synthetic procedures involving multiple
Diels–Alder reactions under harsh extended reaction conditions.
We report a mechanochemical synthesis of structurally well-defined
iptycenes through an iterative reaction sequence, wherein Diels–Alder
reactions and a subsequent aromatization afford higher order iptycenes.
We further report that double Diels–Alder reactions under solvent-free
condition provide facile access to highly functionalized iptycenes
with molecular weights over 2000 Da. Quartz crystal microbalance measurements
reveal that these materials efficiently absorb the aromatic hydrocarbons
benzene and toluene.