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Saturday, May 24, 2008

Using DFT Molecular Orbital Energies to Model Electronic Transitions

J. Org. Chem., 73 (8), 2995 -3004, 2008. 10.1021/jo701676x S0022-3263(70)01676-6
Web Release Date: March 26, 2008

Copyright © 2008 American Chemical Society

Predicting the UV-Vis Spectra of Tetraarylcyclopentadienones: Using DFT Molecular Orbital Energies to Model Electronic Transitions of Organic Materials

Robert G. Potter and Thomas S. Hughes*

Department of Chemistry, Cook Physical Sciences Building, 82 University Place, University of Vermont, Burlington, Vermont 05405

Received August 15, 2007


Tetraphenylcyclopentadienone, due to its intrinsically low HOMO-LUMO gap, has been suggested as a valuable repeat unit in conducting polymers for nanoscale electronics. The HOMO and LUMO of tetraphenylcyclopentadienone appear to be associated with the relevant orbitals of unsubstituted cyclopentadienone. Using previously developed carbonylative coupling reactions, a series of tetraarylcyclopentadienones was synthesized, accessing a range of substituents not previously available. The UV-vis spectra of these molecules were compared to their calculated wave functions and predicted transitions. A quantitative structure-activity relationship was discovered that may greatly simplify prediction of band gaps for oligomers and polymers built from these tetraarylcyclopentadienones.

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