Synthesis and optical properties of phenylene-containing oligoacenes

J Am Chem Soc. 2012 Sep 19;134(37):15351-6. doi: 10.1021/ja3043883. Epub 2012 Sep 5.


Synthesis of a new class of fully unsaturated ladder structures, phenylene-containing oligoacenes (POAs), using 3,4-bis(methylene)cyclobutene as a building block for sequential Diels-Alder reactions is described. The geometric effects of strain and energetic cost of antiaromaticity can be observed via the optical and electrochemical properties of the reported compounds. The resulting shape-persistant ladder structures contain neighboring chromophores that are partially electronically isolated from one another while still undergoing a reduction in the band gap of the material.