Unprecedented perspectives on the application of CinNapht fluorophores provided by a “late-stage” functionalization strategy

Chevalier, Arnaud; Tacke, Eléonore; Hoang, Duc M.; Tatoueix, Kevin; Keromnes, Benoit; Elslande, Elsa Van; Durand, Philippe; Pieters, Grégory

doi:10.1039/d3sc01365k

Chem. Sci.

2023

DOI: 10.1039/d3sc01365k

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Unprecedented perspectives on the application of CinNapht fluorophores provided by a “late-stage” functionalization strategy

Arnaud Chevalier

Eléonore Tacke

Duc M. Hoang

et al.

Abstract: A simple and easy-to-implement process based on an nucleophilic aromatic substitution reaction of a wide variety of nucleophiles on a fluorinated Cin-Napht is described. This process has the key advantage...

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Cited by 4 publications

References 62 publications

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A Naphthalimide Based “Turn‐ON” Probe for Wash‐Free Imaging of Lipid‐Droplet in Living Cells With an Excellent Selectivity

Michel,

Durand,

Chevalier

2024

ChemBioChem

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The impacts of dimethylation of 4‐Amino‐1,8‐ Naphthalimide (ANI) on its photophysical properties are reported. The resulting 4‐DiMe‐ANI displays completely different fluorescence properties, conferring it ability to selectively label lipid droplets in living cells. A comprehensive photophysical study revealed that this selectivity arises from an Internal Charge Transfer favored in lipophilic media to the detriment of a non‐emissive TICT in more polar media. This results in a very high "LDs/Cytosol" signal ratio, enabling LDs to be imaged with an excellent signal‐to‐noise ratio, and positioning its performance above that of the BODIPY 493/503 commonly used to image LDs.

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A Naphthalimide Based “Turn‐ON” Probe for Wash‐Free Imaging of Lipid‐Droplet in Living Cells With an Excellent Selectivity

Michel,

Durand,

Chevalier

2024

ChemBioChem

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Synthesis and Photophysical Properties of 4’‐5’ Disubstituted CinNapht Dyes Accessible through Double SNAr Late‐Stage Functionalization

Tacke,

Estaque,

Hoang

et al. 2024

Chemistry A European J

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This article describes the synthesis of a difluorinated CinNapht derivative in the 4' and 5' positions allowing the easy access to two new families of fluorophores by late‐stage functionalization using SNAr. The first one comprises derivatives incorporating hindered aromatic amines in the 4' and 5' positions, which show redemission in apolar solvents. The second one is obtained through the use of dinucleophiles. Among them, Tetrahydroquinoxaline (THQ) and tetrahydrobenzodiazepine (THB) compounds show strongly redshifted emission. The photophysical properties of all the fluorophores in these two families are studied and rationalized by DFT and TDDFT calculations. The most promising compounds have been used to image living cells by confocal microscopy.

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The how and why of naphthalimide/heterocycle-fused hybrid dyes: an overview of the latest developments in the quest for dyes with innovative optical properties

Chevalier

2023

Org. Biomol. Chem.

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Unprecedented perspectives on the application of CinNapht fluorophores provided by a “late-stage” functionalization strategy

Abstract: A simple and easy-to-implement process based on an nucleophilic aromatic substitution reaction of a wide variety of nucleophiles on a fluorinated Cin-Napht is described. This process has the key advantage...

Cited by 4 publications

References 62 publications

A Naphthalimide Based “Turn‐ON” Probe for Wash‐Free Imaging of Lipid‐Droplet in Living Cells With an Excellent Selectivity

A Naphthalimide Based “Turn‐ON” Probe for Wash‐Free Imaging of Lipid‐Droplet in Living Cells With an Excellent Selectivity

Synthesis and Photophysical Properties of 4’‐5’ Disubstituted CinNapht Dyes Accessible through Double SNAr Late‐Stage Functionalization

The how and why of naphthalimide/heterocycle-fused hybrid dyes: an overview of the latest developments in the quest for dyes with innovative optical properties

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