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    Synthesis and Optical Properties of Phenylene-Containing Oligoacenes
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    Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, Massachusetts 02139, United States
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    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2012, 134, 37, 15351–15356
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    https://doi.org/10.1021/ja3043883
    Published September 5, 2012
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    Abstract

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    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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    Experimental data including synthetic procedures, characterization data for all compounds, and additional figures. This material is available free of charge via the Internet at http://pubs.acs.org.

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    Cite this: J. Am. Chem. Soc. 2012, 134, 37, 15351–15356
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    https://doi.org/10.1021/ja3043883
    Published September 5, 2012
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