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Emerging Prospects for Unusual Aromaticity in Organic Electronic Materials: The Case for Methano[10]annulene
Author(s) -
Peart Patricia A.,
Repka Lindsay M.,
Tovar John D.
Publication year - 2008
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200701102
Subject(s) - annulene , azulene , chemistry , aromaticity , delocalized electron , computational chemistry , context (archaeology) , porphyrin , chemical physics , organic chemistry , molecule , paleontology , biology
Abstract Unusual aromatics outside of the 6π‐electron motif offer promise for functional electronic materials, and we frame this claim in the context of 10π‐electron aromatics. The evolution of our understanding of 10π‐electron aromatics is discussed briefly, from azulene to the [10]annulenes to finally 1,6‐methano[10]annulene. A survey of annulene research of both fundamental and applied nature is then presented. Finally, our recent contributions to this area are highlighted with a comparison of annulene‐based electronic materials to more classical benzenoid counterparts. The annulene core greatly facilitates the delocalization of mobile charges as determined through voltammetry and spectroelectrochemistry. We show that this important hydrocarbon can indeed be viewed as a viable building block for advanced polymeric semiconducting materials.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)