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Coumarin-Rhodamine Hybrids—Novel Probes for the Optical Measurement of Viscosity and Polarity

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Abstract

A comprehensive systematic study of absorption and fluorescence properties in solvents of varying viscosity and polarity of three novel and red-emitting coumarin-rhodamine hybrid derivatives with differences in the rigidity of their substituents is presented. This includes ethanol-polyethylene glycol, toluene-polyethylene glycol, and toluene-paraffin mixtures. Moreover, protonation-induced effects on the spectroscopic properties are studied. A viscosity-induced emission enhancement was observed for all coumarin-rhodamine hybrid derivatives. MCR2 bearing a julolidine donor showed the expected low sensitivity to viscosity whereas MCR3 with its freely rotatable diphenylamino substituent revealed a particularly pronounced sensitivity to this parameter. Moreover, MCR2 shows an enhancement in emission in the open, i.e., protonated form in conjunction with a largely Stokes shift fluorescence in the deep red spectral region. This enables the application of these dyes as viscosity sensors and as far red emitting pH-sensitive probes.

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Acknowledgements

Amol Jadhav is thankful to UGC for UGC-SRF fellowship as well as DST-DAAD, India for Indo - German Academic Exchange Service.

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    Authors and Affiliations

    1. Division 1.10 - Biophotonics, Federal Institute for Materials Research and Testing (BAM), Richard-Willstaetter-Str. 11, 12489, Berlin, Germany

      Norman Scholz, Thomas Behnke, Nithiya Nirmalananthan & Ute Resch-Genger

    2. Department of Dyestuff Technology, Institute of Chemical Technology, N. P. Marg, Matunga, Mumbai, 400 019, Maharashtra, India

      Amol Jadhav, Milind Shreykar & Nagaiyan Sekar

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    1. Norman Scholz
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    Correspondence to Nagaiyan Sekar.

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    Norman Scholz and Amol Jadhav contributed equally.

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    Scholz, N., Jadhav, A., Shreykar, M. et al. Coumarin-Rhodamine Hybrids—Novel Probes for the Optical Measurement of Viscosity and Polarity. J Fluoresc 27, 1949–1956 (2017). https://doi.org/10.1007/s10895-017-2165-4

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