Synthesis and Photophysical Properties of 4’‐5’ Disubstituted CinNapht Dyes Accessible through Double SNAr Late‐Stage Functionalization - Archive ouverte HAL
Article Dans Une Revue Chemistry - A European Journal Année : 2024

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

Résumé

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 red‐emission 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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Chimie organique
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hal-04831123 , version 1 (11-12-2024)

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Eléonore Tacke, Lilian Estaque, Minh-Duc Hoang, P. Durand, Gilles Clavier, et al.. Synthesis and Photophysical Properties of 4’‐5’ Disubstituted CinNapht Dyes Accessible through Double SNAr Late‐Stage Functionalization. Chemistry - A European Journal, In press, ⟨10.1002/chem.202403684⟩. ⟨hal-04831123⟩
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