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Issue 1, 2017
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Keto-polymethines: a versatile class of dyes with outstanding spectroscopic properties for in cellulo and in vivo two-photon microscopy imaging

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Abstract

The synthesis of keto-heptamethine derivatives has been expanded to various new symmetrical and asymmetrical structures, including an unprecedented di-anionic keto-polymethine. The spectroscopic behavior of these new dyes has been systematically and thoroughly investigated, revealing that the formation of hydrogen bond interactions with protic solvents is responsible for a dramatic enhancement of the fluorescence quantum yield in the far-red spectral region. The existence of these strong hydrogen-bond interactions was further confirmed by molecular dynamics simulations. These bis-dipolar polymethines exhibit large two-photon absorption (TPA) cross-sections (σ2 in GM) in the near-infrared, making them ideal candidates for NIR-to-NIR two-photon microscopy imaging applications. We demonstrate that the molecular engineering of the hydrophilic/hydrophobic balance enables targeting of different cellular components, such as cytoplasm or cell membranes. Addition of appropriate substituents provides the molecule with high-water-solubility, affording efficient two-photon probes for angiography.

Graphical abstract: Keto-polymethines: a versatile class of dyes with outstanding spectroscopic properties for in cellulo and in vivo two-photon microscopy imaging

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Publication details

The article was received on 06 Jun 2016, accepted on 01 Aug 2016 and first published on 03 Aug 2016


Article type: Edge Article
DOI: 10.1039/C6SC02488B
Citation: Chem. Sci., 2017,8, 381-394
  • Open access: Creative Commons BY license
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    Keto-polymethines: a versatile class of dyes with outstanding spectroscopic properties for in cellulo and in vivo two-photon microscopy imaging

    S. Pascal, S. Denis-Quanquin, F. Appaix, A. Duperray, A. Grichine, B. Le Guennic, D. Jacquemin, J. Cuny, S. Chi, J. W. Perry, B. van der Sanden, C. Monnereau, C. Andraud and O. Maury, Chem. Sci., 2017, 8, 381
    DOI: 10.1039/C6SC02488B

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