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Luminescent Donor-Acceptor β-Diketones: Modulation of Emission by Solvent Polarity and Group II Metal Binding

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Abstract

A class of aryl trifluoromethyl-containing β-diketones were synthesized via one step Claisen condensation. These π-conjugated diketones exhibit strong solvatochromism from intramolecular donor-acceptor charge transfer (CT). In addition, fluorescence quantum yields (ϕf) and lifetimes (τf) were measured in different solvents. Diketones exhibit bathochromic shifts in emission spectra with increasing solvent polarity. Fluorescence changes upon Group II metal binding were also studied. Despite the relatively simple structure, the anthracene-CF3 diketone, atm, has strong binding affinity for Mg2+. A 70 nm blue shift and sixfold increase in intensity were observed upon addition of only one equivalent MgCl2 in ethanol solution. It also shows selectivity for Mg2+ binding even in the presence of excess Ca2+. Association constant (Ka) calculations suggest atm has two orders of magnitude stronger chelation for divalent magnesium than for calcium. These findings make atm an attractive starting point for molecular probe and light emitting material design.

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Acknowledgements

We thank the National Science Foundation (CHE 0718879 (C. L. F.), CHE 0410061 (J. N. D.)) for support for this research, the Korean Research Foundation for an internship (S. H. K.) and Kwangwoon University for 2008 sabbatical leave (B. H. K.).

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Authors and Affiliations

  1. Department of Chemistry, University of Virginia, Charlottesville, VA, 22904, USA

    Guoqing Zhang, Ruffin E. Evans, J. N. Demas & Cassandra L. Fraser

  2. Department of Chemistry, Kwangwoon University, Seoul, 139-701, Korea

    Shin Han Kim & Byeong Hyo Kim

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  1. Guoqing Zhang
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Correspondence to Cassandra L. Fraser.

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Zhang, G., Kim, S.H., Evans, R.E. et al. Luminescent Donor-Acceptor β-Diketones: Modulation of Emission by Solvent Polarity and Group II Metal Binding. J Fluoresc 19, 881–889 (2009). https://doi.org/10.1007/s10895-009-0487-6

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