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Photophysical and electrochemical properties and temperature dependent geometrical isomerism in alkyl quinacridonediimines
Umeå University, Faculty of Science and Technology, Department of Chemistry. State Key Laboratory of Supramolecular Structure and Materials, College of Chemistry, Jilin University, Changchun, China and Department of Chemistry & Biochemistry, University of Agriculture, Faisalabad, Pakistan.
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
Abstract [en]

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.
National Category
Chemical Sciences
URN: urn:nbn:se:umu:diva-86338DOI: 10.1039/c3nj00477eISI: 000330043700041OAI: diva2:698679
Available from: 2014-02-24 Created: 2014-02-24 Last updated: 2014-02-24Bibliographically approved

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Javed, Iqbal
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