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Published on: October 18, 2018
Synthesis and optical properties of phenylene-containing oligoacenes
Rebecca R Parkhurst1, Timothy M Swager
1Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, Massachusetts 02139, USA.
Abstract:
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.
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