Photophysical and electrochemical properties and temperature dependent geometrical isomerism in alkyl quinacridonediimines
2014 (English)In: New Journal of Chemistry, ISSN 1144-0546, E-ISSN 1369-9261, Vol. 38, no 2, 752-761 p.Article in journal (Refereed) Published
Quinacridone diimines 1-10 were synthesized by the condensation of anilines with alkyl substituted quinacridones (QA). Photophysical and electrochemical properties of the compounds were investigated. Unconventional behavior of absorption spectra suggested a decrease in pi(-)conjugation within the QA skeleton as well as lack of extended pi(-)conjugation between the QA skeleton and the N-phenyl rings. A computational study of compounds 1-10, a variable temperature H-1 NMR study of compounds 2, 7 and 10 (for instance), and single crystal X-ray analysis of 2, 3, 6, 7, 8 and 10 indicated that the anomalous behavior is due to the buckled, non-planar structure of the quinacridones. Moreover the molecules existed in two interconvertible geometric isomeric forms at different temperatures. Molecular orbital calculations were performed at B3LYP/6-31+G(d), B3PW91/6-31G(d) and PBEPBE/6-31G(d) levels of theory at B3PW91/6-31G(d) optimized structures for both isomers of all compounds (1-10); the results obtained are in close agreement with the experimentally determined values.
Place, publisher, year, edition, pages
Royal Society of Chemistry, 2014. Vol. 38, no 2, 752-761 p.
IdentifiersURN: urn:nbn:se:umu:diva-86338DOI: 10.1039/c3nj00477eISI: 000330043700041OAI: oai:DiVA.org:umu-86338DiVA: diva2:698679