Cyclo‑<i>meta</i>‑phenylene
Revisited: Nickel-Mediated Synthesis, Molecular Structures, and Device
Applications
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Abstract
From a one-pot nickel-mediated Yamamoto-type
coupling reaction
of <i>m</i>-dibromobenzene, five congeners of [<i>n</i>]cyclo-<i>meta</i>-phenylenes were synthesized and fully
characterized. The [<i>n</i>]cyclo-<i>meta</i>-phenylenes possessed a commonly shared arylene unit and intermolecular
contacts but varied in packing structures in the crystalline solid
state. Columnar assembly of larger congeners yielded nanoporous crystals
with carbonaceous walls to capture minor protic or aliphatic solvent
molecules. The concise and scalable synthesis allowed exploration
of the macrocyclic hydrocarbons as bipolar charge carrier transport
materials in organic light-emitting diode devices