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Substituent Effects on the Fluorescence Properties of ortho-Carbor­anes: Unusual Emission Behaviour in C-(2′-Pyridyl)-ortho-carboranes

Böhling, L.; Brockhinke, A.; Kahlert, J.; Weber, L.; Harder, R.A.; Yufit, D.S.; Howard, J.A.K.; MacBride, J.A.H.; Fox, M.A.

Substituent Effects on the Fluorescence Properties of ortho-Carbor­anes: Unusual Emission Behaviour in C-(2′-Pyridyl)-ortho-carboranes Thumbnail


Authors

L. Böhling

A. Brockhinke

J. Kahlert

L. Weber

R.A. Harder

D.S. Yufit

J.A.K. Howard

J.A.H. MacBride



Abstract

Seventeen compounds including the parent ortho-, meta- and para-carboranes and derivatives of ortho-carborane were investigated for luminescence in cyclohexane and dichloromethane solutions. Fifteen of these carboranes revealed very weak emissions in the 285–493 nm range. These carboranes may arguably be viewed as non-emissive in solutions at room temperatures. No emissions could be observed for 1,2-dimethyl-ortho-carborane and 2-methyl-1-phenyl-ortho-carborane. The carboranes with a 2′-pyridyl substituent at the cluster carbon atom gave unusual local and charge-transfer emissions indicating that different excited states are generated on photoexcitation. Of all the carboranes investigated, only 2-(diphenylphosphino)-1-phenyl-ortho-carborane, 1,2-diphenyl-ortho-carborane and 1-phenyl-2-(2′-pyridyl)-ortho-carborane are luminescent in the solid state with emissions at 476–612 nm and large Stokes shifts of 12000–13600 cm–1. The solid-state structures of 1,2-bis(2′-pyridyl)- and 1-phenyl-2-(2′-pyridyl)-ortho-carborane were determined by X-ray crystallography.

Citation

Böhling, L., Brockhinke, A., Kahlert, J., Weber, L., Harder, R., Yufit, D., …Fox, M. (2016). Substituent Effects on the Fluorescence Properties of ortho-Carbor­anes: Unusual Emission Behaviour in C-(2′-Pyridyl)-ortho-carboranes. European Journal of Inorganic Chemistry, 2016(3), 403-412. https://doi.org/10.1002/ejic.201501284

Journal Article Type Article
Online Publication Date Jan 4, 2016
Publication Date Jan 4, 2016
Deposit Date Jan 27, 2016
Publicly Available Date Mar 28, 2024
Journal European Journal of Inorganic Chemistry
Print ISSN 1434-1948
Electronic ISSN 1099-0682
Publisher Wiley-VCH Verlag
Peer Reviewed Peer Reviewed
Volume 2016
Issue 3
Pages 403-412
DOI https://doi.org/10.1002/ejic.201501284

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http://creativecommons.org/licenses/by/4.0/

Copyright Statement
© 2016 The Authors. Published by WILEY-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.




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