Synthesis and Photophysical Properties of 4'-5' Disubstituted CinNapht Dyes Accessible through Double SNAr Late-Stage
Eléonore Tacke1, Lilian Estaque2, Minh-Duc Hoang1
1Université Paris-Saclay, CNRS, Institut de Chimie des Substances Naturelles, UPR 2301, 91198, Gif-sur-Yvette, France.
Abstract:
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.
More Related Videos
14:11Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
Published on: June 10, 2021
06:34Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
Published on: June 20, 2014
Related Concept Videos
Aryldiazonium Salts to Azo Dyes: Diazo Coupling
Cycloaddition Reactions: Overview
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Photochemical Electrocyclic Reactions: Stereochemistry
Selection Rules: Photochemical Activation
[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
