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CT-Operated Bifunctional Fluorescent Probe Based on a Pretwisted Donor–Donor–Biphenyl

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Taking into account the structural requirements for TICT-type sensor molecules, a general synthetic route to derive pH and cation-responsive pretwisted donor (D)–donor (D) biphenyls (b) equipped with donor receptors is developed and a first model compound containing a mono aza-15-crown-5 and a DMA receptor is synthesized, see Scheme 1. The spectroscopic properties of this new bifunctional D–D biphenyl are studied in the non-polar and polar solvents cyclohexane, acetonitrile, and methanol. Protonation as well as complexation studies are performed with the representative metal ions Na(I), K(I), Ca(II), Ag(I), Zn(II), Cd(II), Hg(II), and Pb(II) to reveal the potential of this molecule for communication of whether none, only one, or both binding sites are engaged in analyte coordination by spectroscopically distinguishable outputs. The results are compared to those obtained with closely related donor (D)–acceptor (A) substituted biphenyl-type sensor molecules and are discussed within the framework of neutral and ionic D – A biphenyls.

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Scheme 1.
Scheme 2.
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Scheme 3.

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ACKNOWLEDGMENTS

Financial support from the Deutsche Forschungsgemeinschaft (DFG: grant RE387/8-3 and 436UKR113/24-3) is gratefully acknowledged. We are indebted to Dr. D. Pfeifer for provision of the spectral correction curves, Drs. K. Rurack and W. Weigel for help with the time-resolved fluorescence measurements, and Mrs. A. Rothe for help with the figures.

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Authors and Affiliations

  1. Federal Institute for Materials Research and Testing (BAM), Working Group Optical Spectroscopy, Berlin, Germany

    Y. Q. Li, U. Resch-Genger & M. Spieles

  2. National Nanotechnology Laboratory, Lecce University, Lecce, Italy

    Y. Q. Li

  3. Institute of Organic Chemistry, National Academy of Sciences of the Ukraine, Kiev, Ukraine

    J. L. Bricks

  4. Institut für Chemie, Humboldt Universität zu Berlin, Berlin, Germany

    W. Rettig

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Li, Y., Bricks, J., Resch-Genger, U. et al. CT-Operated Bifunctional Fluorescent Probe Based on a Pretwisted Donor–Donor–Biphenyl. J Fluoresc 16, 337–348 (2006). https://doi.org/10.1007/s10895-005-0035-y

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