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Photocatalysis and self-catalyzed photobleaching with covalently-linked chromophore-quencher conjugates built around BOPHY

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Abstract

Two Chromophore-Quencher Conjugates (CQCs) have been synthesized by covalent attachment of the anti-oxidant dibutylated-hydroxytoluene (BHT) to a pyrrole-BF2 chromophore (BOPHY) in an effort to protect the latter against photofading. In fluid solution, light-induced intramolecular charge transfer is favoured in polar solvents and helps to inhibit photo-bleaching of the chromophore. The rate of photo-fading, which scales with the number of BHT residues, is zero-order in polar solvents but shows a linear dependence on the number of absorbed photons. The zero-order rate constant shows an inverse correlation with the fluorescence quantum yield measured in the same solvent. Photo-bleaching in benzonitrile involves autocatalysis while reaction in cyclohexane shows an unexpected stoichiometry. NMR spectroscopy indicates initial damage takes place at the BHT unit and allows identification of a reactive hydroperoxide as being the primary product. In the presence of an adventitious substrate, this hydroperoxide is a photocatalyst for amide formation under mild conditions.

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Acknowledgements

We thank EPSRC for the award of an Industrial CASE award (OJW) and Newcastle University for financial support of this work. We also thank the EPSRC Mass Spectrometry service at Swansea for access to facilities.

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  1. Molecular Photonics Laboratory, School of Natural and Environmental Sciences (Chemistry), Newcastle University, Bedson Building, Newcastle upon Tyne, NE1 7RU, UK

    Dumitru Sirbu, Owen J. Woodford, Andrew C. Benniston & Anthony Harriman

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Sirbu, D., Woodford, O.J., Benniston, A.C. et al. Photocatalysis and self-catalyzed photobleaching with covalently-linked chromophore-quencher conjugates built around BOPHY. Photochem Photobiol Sci 17, 750–762 (2018). https://doi.org/10.1039/c8pp00162f

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