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- Title
Functionalized thienoacridines: synthesis, optoelectronic, and structural properties.
- Authors
Robertson, Sean F.; Leitch, Alicea A.; Korobkov, Ilia; Soldatov, Dmitriy V.; Brusso, Jaclyn L.
- Abstract
The preparation and characterization of hexylated, brominated, and 5-hexyl-2-thienyl-substituted tetrathienoacridine (TTAc) is described. Comparative electrochemical, optical, computational, and solid-state studies with their thienoanthracene (TTAn) analogs demonstrate that replacement of CH with nitrogen leads to an overall lowering of the frontier molecular energy levels and decrease in the HOMO-LUMO energy gap. While the brominated TTAc and TTAn derivatives are isostructural, as indicated by X-ray diffraction studies, the lower sublimation temperature and thermochromic behaviour exhibited by bromo-TTAc is attributed to an additional dipole−dipole interaction resulting from the dipole moment afforded by carbon/nitrogen substitution in the core aromatic ring. This work represents a fundamental study of heteroatom substitution in 2-D conjugated small molecules and investigates how inclusion of an electron deficient aromatic ring into the molecular framework (i.e., acridine versus anthracene) can influence the physical properties.
- Subjects
OPTOELECTRONIC detectors; CHEMICAL synthesis; SUBSTITUENTS (Chemistry); MOLECULAR energy levels (Quantum mechanics); ANTHRACENE; THERMOCHROMISM; HETEROCYCLIC chemistry; OXIDATION
- Publication
Canadian Journal of Chemistry, 2014, Vol 92, Issue 11, p1106
- ISSN
0008-4042
- Publication type
Article
- DOI
10.1139/cjc-2014-0348