Hydrogen bonding between carboxylic acids and pyridines can be used as
a means of chain extension. However, the reversibility of hydrogen bo
nd formation does not allow the chain-extended structure to be fixed,
and a temperature-dependent chain length results. Complexation between
a tetrapyridyl species and a diacid is shown to counteract the revers
ibility of the hydrogen bonding. These complexes form thermoreversible
three-dimensional supramolecular networks which have properties typic
al of low molar mass materials at high temperatures but polymeric prop
erties at low temperatures. The complexes exhibited a glass transition
and could form fibers from the melt yet exhibited a low-viscosity iso
tropic liquid at elevated temperatures. Atypically, a complex incorpor
ating a 2,2',6,6'-tetrasubstituted biphenyl moiety was found to be liq
uid crystalline.