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Scale-up Chemical Synthesis of Thermally-activated Delayed Fluorescence Emitters Based on the Dibenzothiophene-S,S-Dioxide Core
Published on: October 24, 2017
Intramolecular Charge Transfer in Antiaromatic Donor/Acceptor-Fused s-Indacenes
Isabella S Demachkie1, Michael P Miller1, Gabrielle I Warren1
1Department of Chemistry and Biochemistry and the Materials Science Institute, University of Oregon, Eugene, Oregon, 97403-1253, United States.
Abstract:
Herein we report the synthesis and characterization of four donor/acceptor-fused s-indacenes via the late-stage oxidation of a family of unsymmetrical benzofuran/benzothiophene-s-indacene regioisomers. A thorough study of their properties through experimental and computational analysis has revealed the effect of asymmetry on the molecular properties associated with antiaromaticity, as well as a strong correlation between antiaromaticity and intramolecular charge transfer (ICT). The strength of the charge transfer depends on the fusion orientation of the donor and acceptor motifs relative to the s-indacene core. The two most antiaromatic oxidized isomers exhibit strong evidence of ICT with 30 and 40 nm solvatochromic shifts.
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