Abstract
Three isomers of quinodimethanes (QDMs) adopt different electronic configurations and geometries, generating their own characteristic physical properties. Incorporation of QDMs into non-benzenoid aromatic or antiaromatic frameworks not only planarizes the whole p system optimizing conjugation, but also changes the electronic properties inherent to QDMs, sometimes drastically, due to the topology of the p system, through interaction with the remaining part of the molecules. In non-benzenoid systems, molecular orbital levels and orbital distribution are uneven compared to benzenoid systems, thereby polarizing the ground state and leading to unique behavior in excited states. In antiaromatic systems, openshell, diradical character, which is inherent to QDMs, may be enhanced due to small HOMO‑LUMO energy gap. In this chapter, effects of incorporating QDMs into non-benzenoid aromatic or antiaromatic frameworks are discussed focusing on the open-shell, diradical character with respect to their molecular structures, antiaromaticity, and physical properties related to the open-shell character and molecular orbital levels and materials applications, as well as covering historical works to the current state-of-the-art achievements.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2018 Springer International Publishing AG, part of Springer Nature
About this chapter
Cite this chapter
Tobe, Y. (2018). Quinodimethanes Incorporated in Non‑Benzenoid Aromatic or Antiaromatic Frameworks. In: Tobe, Y., Kubo, T. (eds) Physical Organic Chemistry of Quinodimethanes. Topics in Current Chemistry Collections. Springer, Cham. https://doi.org/10.1007/978-3-319-93302-3_3
Download citation
DOI: https://doi.org/10.1007/978-3-319-93302-3_3
Received:
Accepted:
Published:
Publisher Name: Springer, Cham
Print ISBN: 978-3-319-93301-6
Online ISBN: 978-3-319-93302-3
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)