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Iterative synthesis, structures, and properties of acyclic and cyclic acridone oligomers

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Acyclic and cyclic acridone-2,7-diyl oligomers were synthesized by an iterative procedure from 10-mesitylacridone as heteroatom containing π-conjugated compounds. The oligomeric chain was elongated by a combination of regioselective bromination, borylation, Ni(0)-mediated homocoupling, and Suzuki-Miyaura coupling up to acyclic hexamer. Subsequently, the cyclic hexamer was synthesized by the bromination and intramolecular coupling of the acyclic hexamer. The DFT calculations revealed that the acyclic oligomers preferred to take extended structures with anti conformations, whereas the cyclic hexamer took a macrocyclic structure with syn conformations. The UV/Vis and fluorescence spectra of the series of oligomers were measured, and the effects of the chain length and the cyclization are discussed in terms of π-conjugation.

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