Synthesis and Photophysical Properties of 4’‐5’ Disubstituted CinNapht Dyes Accessible through Double SNAr Late‐Stage Functionalization DOI Creative Commons
Arnaud Chevalier,

Eléonore Tacke,

Lilian Estaque

et al.

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 14, 2024

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

Language: Английский

Unlocking the potential of hydrogen deuterium exchange via an iterative continuous-flow deuteration process DOI Creative Commons

Kevin Tatoueix,

Marco Lepron,

Cédric Barboux

et al.

Nature Communications, Journal Year: 2025, Volume and Issue: 16(1)

Published: Feb. 3, 2025

Labelled compounds bearing hydrogen isotopes are keystones in diverse areas constituting a multi-billion dollar global market including drugs, diagnostics, biology, toxicology and smart materials. While deuterium exchange (HDE) methods hold promise as relevant tools for the late-stage one-step preparation of deuterium-labelled compounds, they often fall short achieving sufficient isotopic purity combined either with site-selectivity or full deuteration process, highlighting need further development optimisation. This report pinpoints an approach to unlock potential HDE using concept iterative runs continuous-flow technology (recirculation process). closed-loop process grants access now deuterated high purities, labelled at precise site perdeuterated on demand, fast, productive, environmentally friendly way. Hydrogen but process. Here, authors technology.

Language: Английский

Citations

0
Annulation-induced hidden reactivity of N-(2-ethynylaryl)-1,2,3-triazoles to cinnolines under microwave irradiation DOI Creative Commons

Yangang Wu,

Chaewon Yi,

L.‐G. LIN

et al.

Green Synthesis and Catalysis, Journal Year: 2025, Volume and Issue: unknown

Published: March 1, 2025

Language: Английский

Citations

0
CinNapht AIE(E)gens for selective imaging of lipid droplets DOI

Eléonore Tacke,

Minh‐Duc Hoang,

Lilian Estaque

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(14), P. 2739 - 2743

Published: Jan. 1, 2024

The use of hindered aromatic amines in a SNAr reaction enabled the synthesis novel AIE(E)gens derivatives CinNaphts, suitable for fluorescence imaging lipid droplets living cells.

Language: Английский

Citations

2
A Naphthalimide Based “Turn‐ON” Probe for Wash‐Free Imaging of Lipid‐Droplet in Living Cells With an Excellent Selectivity DOI Creative Commons

Laurane Michel,

Philippe Durand, Arnaud Chevalier

et al.

ChemBioChem, Journal Year: 2024, Volume and Issue: unknown

Published: April 29, 2024

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

Language: Английский

Citations

1
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 DOI
Arnaud Chevalier

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(37), P. 7498 - 7510

Published: Jan. 1, 2023

In this review, a variety of hybrid structures fusing aromatic heterocycles different natures to naphthalimide backbone are discussed.

Language: Английский

Citations

2
Synthesis and Photophysical Properties of 4’‐5’ Disubstituted CinNapht Dyes Accessible through Double SNAr Late‐Stage Functionalization DOI Creative Commons
Arnaud Chevalier,

Eléonore Tacke,

Lilian Estaque

et al.

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 14, 2024

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

Language: Английский

Citations

0