Please use this identifier to cite or link to this item: https://doi.org/10.1002/chem.201102120
Title: Lateral extension of π conjugation along the bay regions of bisanthene through a diels-alder cycloaddition reaction
Authors: Li, J.
Jiao, C.
Huang, K.-W.
Wu, J. 
Keywords: cycloaddition
dyes/pigments
hyperconjugation
Michael addition
polycycles
Issue Date: 16-Dec-2011
Citation: Li, J., Jiao, C., Huang, K.-W., Wu, J. (2011-12-16). Lateral extension of π conjugation along the bay regions of bisanthene through a diels-alder cycloaddition reaction. Chemistry - A European Journal 17 (51) : 14672-14680. ScholarBank@NUS Repository. https://doi.org/10.1002/chem.201102120
Abstract: Diels-Alder cycloaddition reactions at the bay regions of bisanthene (1) with dienophiles such as 1,4-naphthoquinone have been investigated. The products were submitted to nucleophilic addition followed by reductive aromatization reactions to afford the laterally extended bisanthene derivatives 2 and 3. Attempted synthesis of a larger expanded bisanthene 4 revealed an unexpected hydrogenation reaction at the last reductive aromatization step. Unusual Michael addition was observed on quinone 14, which was obtained by Diels-Alder reaction between 1 and 1,4-anthraquinone. Compounds 1-3 exhibited near-infrared (NIR) absorption and emission with high-to-moderate fluorescent quantum yields. Their structures and absorption spectra were studied by density function theory and non-planar twisted structures were calculated for 2 and 3. All compounds showed amphoteric redox behavior with multiple oxidation/reduction waves. Oxidative titration with SbCl 5 gave stable radical cations, and the process was followed by UV/Vis/NIR spectroscopic measurements. Their photostability was measured and correlated to their different geometries and electronic structures. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Source Title: Chemistry - A European Journal
URI: http://scholarbank.nus.edu.sg/handle/10635/94139
ISSN: 09476539
DOI: 10.1002/chem.201102120
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