Influence of Donor-Substituents on Triphenylamine Chromophores Bearing Pyridine Fragments - Archive ouverte HAL Access content directly
Journal Articles European Journal of Organic Chemistry Year : 2019

Influence of Donor-Substituents on Triphenylamine Chromophores Bearing Pyridine Fragments

(1) , (1) , (2) , (1) , (1) , (3) , (2) , (2)
1
2
3

Abstract

Efficient synthetic routes that combine different palladium-catalyzed cross-coupling reactions have been developed for the preparation of a new family of push-pull derivatives in which pyridine was used as the acceptor group and different para-substituted diphenylamines as the donor groups. All compounds showed absorption in the UV/Vis region and blue-green emission with high quantum yields. Significant red shifts were observed in the absorption and fluorescence emission maxima on increasing the electron-donating ability of the substituents or on incorporating a pi-conjugated linker. This finding can be explained on the basis of enhanced intramolecular charge transfer (ICT). Strong emission solvatochromism confirmed the formation of an intramolecular charge-separated emitting state. The HOMO-LUMO energy gaps have been estimated by experimental electrochemical measurements and the results were interpreted with the aid of DFT calculations. The thermal behavior of all materials has also been studied by differential scanning calorimetry.
Fichier principal
Vignette du fichier
Tydlitat et al_Influence of donor-substituents on triphenylamine chromophores bearing pyridine.pdf (437.09 Ko) Télécharger le fichier
Origin : Files produced by the author(s)
Loading...

Dates and versions

hal-02086459 , version 1 (16-04-2019)

Identifiers

Cite

Jiri Tydlitat, Michaela Fecková, Pascal Le Poul, Oldrich Pytela, Milan Klikar, et al.. Influence of Donor-Substituents on Triphenylamine Chromophores Bearing Pyridine Fragments. European Journal of Organic Chemistry, 2019, 2019 (9), pp.1921-1930. ⟨10.1002/ejoc.201900026⟩. ⟨hal-02086459⟩
37 View
117 Download

Altmetric

Share

Gmail Facebook Twitter LinkedIn More