Synthesis of Oligo(1,8-pyrenylene)s: A Series of Functional Molecular Liquids

A monomer-through-pentamer series of oligo(1,8-pyrenylene)s was synthesized using a two-step iterative synthetic strategy. The trimer, tetramer, and pentamer are mixtures of atropisomers that interconvert slowly at room temperature (as shown by variable-temperature NMR analysis). They are liquids well below room temperature, as indicated by POM, DSC and SWAXS analysis. These oligomers are highly fluorescent both in the liquid state and in dilute solution (λ_F,max = 444-457 nm, φ_F = 0.80) and an investigation of their photophysical properties demonstrated that delocalization plays a larger role in their excited states than it does in related pyrene-based oligomers.