C‐Functionalized Cationic Diazaoxatriangulenes: Late‐Stage Synthesis and Tuning of Physicochemical Properties. Issue 40 (25th June 2018)

• Record Type: Journal Article
• Authors: Delgado, Irene Hernández; Pascal, Simon; Besnard, Céline; Voci, Silvia; Bouffier, Laurent; Sojic, Neso; Lacour, Jérôme
• Is Part Of: Chemistry. Volume 24:Issue 40(2018)
• Page Start: 10186
• Page End: 10195
• Publication Date: 2018-06-25
• Subjects: dyes/pigments -- electrochemistry -- fluorescence -- substituent effects -- synthesis design; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201801486
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: A series of nine C‐functionalized cationic diazaoxatriangulene (DAOTA) dyes have been successfully synthesized and fully characterized, including X‐ray structural analysis of four derivatives. The introduction of electron‐withdrawing or ‐donating functions enables the tuning of both electro‐ and photochemical properties with, for instance, two consecutive (reversible) reductions or oxidations observed for nitro or amino derivatives, respectively. The substituents also impacted on the optical properties, with absorption maxima varying from λ =528 to 640 nm and fluorescence being shifted from the yellow to the red range, up to λ =656 nm. Abstract : Peripheral vision : A series of nine C‐functionalized cationic diazaoxatriangulene dyes (DAOTA) have been successfully synthesized and fully characterized. The regioselective functionalization of cationic DAOTA is a simple and efficient strategy to tune the electrochemical and photophysical properties of this class of dyes and fluorophores (see figure).