Journal article

Publication year: 2008

Pages: 5048-5063

Journal: The Journal of Organic Chemistry

Volume number: 73

Issue number: 13

ISSN: 0022-3263

DOI Link: https://doi.org/10.1021/jo8005123

Publisher: American Chemical Society

Abstract: 

oward the goal of preparing stable, neutral open-shell systems, we synthesized a novel series of p-phenyl-substituted
3,5,7,9-hexaazaacridine and 3,5,7,9-hexaazaanthracene derivatives. The
effects of substitution on the molecular electronic properties were
probed both experimentally and computationally
[B3LYP/6-311G(d,p)//B3LYP/6-31G(d,p)]. While the experimentally prepared
structures already have small (20−25 kcal/mol) singlet−triplet energy
gaps, systems with even smaller (<9 kcal/mol) singlet−triplet energy
separations can be realized through systematic variation of the
substituent numbers, types, and patterns. Hexaazaanthracenes show
generally smaller singlet−triplet energy gaps than hexaazaacridines.
Nitrogen-bonded σ- and π-acceptor substituents that cause positive
inductive and mesomeric effects as well as carbon-bonded σ-donor
substituents make substituted hexaazaanthracenes promising candidates
for purely organic high-spin systems.

Harvard Citation style: Langer, P., Amiri, S., Bodtke, A., Saleh, N., Weisz, K., Görls, H., et al. (2008) 3,5,7,9-Substituted Hexaazaacridines: Toward Structures with Nearly Degenerate Singlet−Triplet Energy Separations, The Journal of Organic Chemistry, 73(13), pp. 5048-5063. https://doi.org/10.1021/jo8005123

APA Citation style: Langer, P., Amiri, S., Bodtke, A., Saleh, N., Weisz, K., Görls, H., & Schreiner, P. (2008). 3,5,7,9-Substituted Hexaazaacridines: Toward Structures with Nearly Degenerate Singlet−Triplet Energy Separations. The Journal of Organic Chemistry. 73(13), 5048-5063. https://doi.org/10.1021/jo8005123