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C‐Functionalized Cationic Diazaoxatriangulenes: Late‐Stage Synthesis and Tuning of Physicochemical Properties
Author(s) -
Delgado Irene Hernández,
Pascal Simon,
Besnard Céline,
Voci Silvia,
Bouffier Laurent,
Sojic Neso,
Lacour Jérôme
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201801486
Subject(s) - cationic polymerization , nitro , fluorescence , absorption (acoustics) , photochemistry , chemistry , materials science , combinatorial chemistry , polymer chemistry , organic chemistry , optics , alkyl , physics , composite material
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.