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|Title:||Lateral extension of π conjugation along the bay regions of bisanthene through a diels-alder cycloaddition reaction|
|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|
|Appears in Collections:||Staff Publications|
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