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|Title:||Synthesis, optical and electrochemical properties of isomeric dibenzophenanthroline derivatives||Authors:||Ghosh, Animesh
Morris, Samuel Alexander
Webster, Richard David
Gurzadyan, Gagik G.
Grimsdale, Andrew C.
|Keywords:||Science::Chemistry::Organic chemistry||Issue Date:||2021||Source:||Ghosh, A., Li, T., Ni, W., Wu, T., Liang, C., Budanovic, M., Morris, S. A., Klein, M., Webster, R. D., Gurzadyan, G. G. & Grimsdale, A. C. (2021). Synthesis, optical and electrochemical properties of isomeric dibenzophenanthroline derivatives. Asian Journal of Organic Chemistry. https://dx.doi.org/10.1021/acs.jcpb.1c07045||Project:||RG117/15
|Journal:||Asian Journal of Organic Chemistry||Abstract:||Acid catalysed Friedländer cyclization of 2-aminobenzophenones with 1,2-, 1,3-, and 1,4-cyclohexadiones, followed by aromatization, has been used to prepare dibenzophenanthrolines (DBPs) containing 1,10-, 1,7- and 4,7-phenanthroline units, whose optoelectronic properties have been compared. The LUMO energies for all isomers were similar but the 4,7-isomers possessed significantly higher HOMOs than the other isomers, resulting in them having smaller HOMO-LUMO energy gaps. Compared with 1,10-DBP isomers, the emission of 1,7-DBPs is strongly quenched due to efficient charge transfer. The 4,7-DBP isomers show strongly enhanced photoluminescence due to excimer formation but appear to be less photostable due to their higher HOMO levels. Bis(phenylethynyl)-substituted derivatives demonstrated improved solubility and stronger luminescence properties than their unsubstituted analogues.||URI:||https://hdl.handle.net/10356/153444||ISSN:||2193-5807||DOI:||10.1021/acs.jcpb.1c07045||Rights:||This is the peer reviewed version of the following article: Ghosh, A., Li, T., Ni, W., Wu, T., Liang, C., Budanovic, M., Morris, S. A., Klein, M., Webster, R. D., Gurzadyan, G. G. & Grimsdale, A. C. (2021). Synthesis, optical and electrochemical properties of isomeric dibenzophenanthroline derivatives. Asian Journal of Organic Chemistry, which has been published in final form at https://doi.org.remotexs.ntu.edu.sg/10.1002/ajoc.202100670. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions.||Fulltext Permission:||embargo_20221130||Fulltext Availability:||With Fulltext|
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