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Enantioselective phosphorescence behavior of naproxen in β-cyclodextrin supramolecular complex

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Abstract

In the presence of small amount of 1-iodo butane (IBu) (0.1 % (v/v)), Naproxen (Nap) displays strong room temperature phosphorescence (RTP) in β-cyclodextrin (β-CD) solution without deoxygenation because of the formation of ternary complex of β-CD, Nap, and IBu. The results indicate that β-CD shows good enantiodiscrimination for (R)-Nap and (S)-Nap. The RTP intensity of (R)-Nap is larger than that of (S)-Nap, the difference being 29.2 %. Both (R)-Nap and (S)-Nap exhibit single exponential phosphorescence decay with different lifetimes of 2.535 ± 0.056 and 1.798 ± 0.076 ms for (R)-Nap and for (S)-Nap, respectively. The corresponding association constants evaluated for (R)-Nap/β-CD/IBu and (S)-Nap/β-CD/IBu ternary complexes are (8.02 ± 0.15) × 103 and (2.50 ± 0.06) × 103 L mol−1, respectively. Thus, the observation of RTP differences between (R)-Nap and (S)-Nap can be attributed to their different ability to form complexes with chiral β-CD.

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Acknowledgments

This work was financially supported by the Natural Science Foundation of Shanxi Province (No. 2008011015-1), the Project Sponsored by the Scientific Research Foundation for the Returned Overseas Chinese Scholars, State Education Ministry and Research Project Supported by Shanxi Scholarship Council of China (2011-008).

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Authors and Affiliations

  1. School of Chemistry and Chemical Engineering, Shanxi University, Taiyuan, 030006, People’s Republic of China

    Y. Wang, T. T. Feng, L. L. Shi, F. Liu & Z. B. Shang

  2. College of Chemistry, Beijing Normal University, Beijing, 100875, China

    W. J. Jin

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Wang, Y., Feng, T.T., Shi, L.L. et al. Enantioselective phosphorescence behavior of naproxen in β-cyclodextrin supramolecular complex. J Incl Phenom Macrocycl Chem 76, 151–158 (2013). https://doi.org/10.1007/s10847-012-0184-y

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