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Antiaromaticity in Nonbenzenoid Oligoarenes and Ladder Polymers

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Polyarenes II

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 350))

Abstract

Polycyclic aromatic hydrocarbons (PAHs) and fully-conjugated ladder polymers are leading candidates for organics electronics, as their inherent conformational rigidity encourages electron delocalization. Many of these systems consist of fused benzenoid or heterocyclic aromatic rings. Less frequently, however, PAHs are reported with character that alternates between the aromaticity of benzene fragments and the antiaromaticity of a nonbenzenoid moiety. This chapter will focus on recent work published on the theory, synthesis, and properties of two such systems: [N]phenylenes containing 4π-electron cyclobutadienoid character, and diaryl[a,e]pentalenes containing 8π-electron pentalenoid character.

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Acknowledgements

The support of the National Science Foundation DMR-1005810 and the Center for Excitonics, an Energy Frontier Research Center funded by the U.S. Department of Energy, Office of Science, Office of Basic Energy Sciences under Award Number DE-SC0001088, is greatly appreciated.

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Authors and Affiliations

  1. Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA, US

    Rebecca R. Parkhurst & Timothy M. Swager

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  1. Rebecca R. Parkhurst
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Correspondence to Rebecca R. Parkhurst .

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Editors and Affiliations

  1. School of Pharmaceutical Science and Technology, Tianjin University, Tianjin, China

    Jay S. Siegel

  2. Department of Chemistry, National Cheng Kung University, Tainan, Taiwan

    Yao-Ting Wu

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Parkhurst, R.R., Swager, T.M. (2014). Antiaromaticity in Nonbenzenoid Oligoarenes and Ladder Polymers. In: Siegel, J., Wu, YT. (eds) Polyarenes II. Topics in Current Chemistry, vol 350. Springer, Cham. https://doi.org/10.1007/128_2012_387

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