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The donor–acceptor biphenyl platform: A versatile chromophore for the engineering of highly efficient two-photon sensitive photoremovable protecting groups

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Abstract

Different photoremovable protecting groups in the o-nitrobenzyl, phenacyl, and 2-(o-nitrophenyl)propyl series with a donor–acceptor biphenyl backbone, known to display excellent two-photon absorption cross-sections, were investigated in order to develop efficient two-photon sensitive photoremovable protecting groups. The 2-(o-nitrophenyl)propyl series was a more versatile platform to increase the two-photon sensitivity of photoremovable protecting groups, leading to the p-alkoxy and p-bisalkylamino-4-nitro-[1,1′-biphenyl]-3-yl)propyl derivatives: PENB and EANBP respectively. Those two photoremovable protecting groups are to date the best caging groups for two-photon excitation at 800 and 740 nm respectively, offering attracting perspectives in chemical biology.

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Authors and Affiliations

  1. Laboratoire de Conception et Application de Molécules Bioactives, UMR 7199, CNRS/UDS, Faculté de Pharmacie, 74 Route du Rhin, 67401, ILLKIRCH Cedex, France

    Alexandre Specht, Loïc Donato, Cyril Herbivo, Sébastien Charon, David Warther, Sylvestre Gug & Maurice Goeldner

  2. Laboratoire de Biophotonique et Pharmacologie, UMR 7213, CNRS/UdS, Faculté de Pharmacie, 74 Route du Rhin, 67401, ILLKIRCH Cedex, France

    Frédéric Bolze, Sylvestre Gug & Jean-François Nicoud

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  1. Alexandre Specht
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  2. Frédéric Bolze
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  3. Loïc Donato
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  4. Cyril Herbivo
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  9. Maurice Goeldner
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Correspondence to Alexandre Specht or Maurice Goeldner.

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Specht, A., Bolze, F., Donato, L. et al. The donor–acceptor biphenyl platform: A versatile chromophore for the engineering of highly efficient two-photon sensitive photoremovable protecting groups. Photochem Photobiol Sci 11, 578–586 (2012). https://doi.org/10.1039/c2pp05360h

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  • DOI: https://doi.org/10.1039/c2pp05360h

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