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Optimization in Solvent Selection for Chlorin e6 in Photodynamic Therapy

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Abstract

The photophysical properties of chlorin e6 (Ce6) in twelve different protic, aprotic and non-polar solvents were investigated using ultraviolet–visible and fluorescence spectroscopic methods. Solvatochromic effects were determined by the changes in quantum yield, Stokes shift, fluorescence half-life and excited state dipole moments of Ce6 in the different solvents. The absorption shifts observed in different solvents were further analyzed using the Kamlet-Abboud-Taft model and the nature of solute-solvent interactions between Ce6 and different protic and aprotic solvents was elucidated. The quantum yields were found highest in protic solvents (except water), followed by aprotic and non-polar solvents. Solvent polarity parameters showed a linear increasing trend with Stokes shift and fluorescence half-life, which indicated the presence of Ce6-solvent interaction. Using the Kamlet-Abboud-Taft model, a direct correlation between the solvent polarity parameters and absorption shift was observed, which substantiated the existence of Ce6-solvent interaction by hydrogen bond formation. The excited state dipole moments in specific protic and aprotic solvents were found to be higher than the ground state dipole moments, implying a more polar nature of Ce6 during excited state transition.

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Acknowledgments

This research is supported by the Singapore Ministry of Health’s National Medical Research Council under IRG NMRC/1187/2008 (R-148-000-114-213) and GEA-NUS PPRL fund (N-148-000-008-001). There is no conflict of interest.

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  1. Department of Pharmacy, Faculty of Science, National University of Singapore, 18 Science Drive 4, Singapore, 117543, Singapore

    Shubhajit Paul, Paul Wan Sia Heng & Lai Wah Chan

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  1. Shubhajit Paul
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  2. Paul Wan Sia Heng
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  3. Lai Wah Chan
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Correspondence to Lai Wah Chan.

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Paul, S., Heng, P.W.S. & Chan, L.W. Optimization in Solvent Selection for Chlorin e6 in Photodynamic Therapy. J Fluoresc 23, 283–291 (2013). https://doi.org/10.1007/s10895-012-1146-x

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  • DOI: https://doi.org/10.1007/s10895-012-1146-x

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