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Double-tailed Long Chain BODIPYs - Synthesis, Characterization and Preliminary Studies on their use as Lipid Fluorescence Probes

Lookup NU author(s): Professor Andrew Benniston, Emeritus Professor Anthony Harriman

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Abstract

© 2017 Elsevier B.V. In this paper we report the synthesis of a series of double-tailed BODIPYs bearing twin alkoxy groups with long linear alkyl side chains (C10, C12, C14, C16) attached to the meso positioned phenyl unit. The compounds were fully characterized and exhibited the typical BODIPY strong absorbance in the visible region and emission maxima around 530 nm, with high fluorescence quantum yields (ca. 0.8) and small Stokes shifts. The goal was to improve the lipophilicity of the BODIPYs without disturbing their excellent fluorescent properties. All synthetized BODIPYs were tested in vivo as fluorescent sensors for lipids and one of them (BD-C12) showed great potential to act as a lipid fluorescent probe.

Publication metadata

Author(s): Arranja C, Aguiar A, Encarnação T, Fonseca S, Justino L, Castro R, Benniston AC, Harriman A, Burrows H, Sobrala AJFN

Publication type: Article

Publication status: Published

Journal: Journal of Molecular Structure

Year: 2017

Volume: 1146

Pages: 62

Print publication date: 15/10/2017

Online publication date: 29/05/2017

Acceptance date: 25/05/2017

ISSN (print): 0022-2860)

Publisher: Elsevier

URL: https://doi.org/10.1016/j.molstruc.2017.05.119

DOI: 10.1016/j.molstruc.2017.05.119

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