Hydrogen bonding interactions can decrease clar sextet character in acridone pigments.

Org Biomol Chem

Department of Chemistry, University of Houston, Houston, Texas 77204, USA.

Published: November 2021

Computed nucleus-independent chemical shifts (NICS), contour plots of isotropic magnetic shielding (IMS), and gauge-including magnetically induced current (GIMIC) plots suggest that polarization of the π-system of acridones may perturb the numbers and positions of Clar sextet rings. Decreasing numbers of Clar sextets are connected to experimental observations of a narrowing HOMO-LUMO gap and increased charge mobility in solid-state assemblies of quinacridone and epindolidione.

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http://dx.doi.org/10.1039/d1ob01720aDOI Listing

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