Article Dans Une Revue Materials Année : 2019

Push-Pull Chromophores Based on the Naphthalene Scaffold: Potential Candidates for Optoelectronic Applications

Résumé

A series of ten push-pull chromophores comprising 1H-cyclopenta[b]naphthalene-1,3(2H)-dione as the electron-withdrawing group have been designed, synthesized, and characterized by UV-visible absorption and fluorescence spectroscopy, cyclic voltammetry and theoretical calculations. The solvatochromic behavior of the different dyes has been examined in 23 solvents and a positive solvatochromism has been found for all dyes using the Kamlet-Taft solvatochromic relationship, demonstrating the polar form to be stabilized in polar solvents. To establish the interest of this polyaromatic electron acceptor only synthesizable in a multistep procedure, a comparison with the analog series based on the benchmark indane-1,3-dione (1H-indene-1,3(2H)-dione) has been done. A significant red-shift of the intramolecular charge transfer band has been found for all dyes, at a comparable electron-donating group. Parallel to the examination of the photophysical properties of the different chromophores, a major improvement of the synthetic procedure giving access to 1H-cyclopenta[b]naphthalene-1,3(2H)-dione has been achieved.

Domaines

Fichier principal
Vignette du fichier
materials-12-01342.pdf (3.31 Mo) Télécharger le fichier
Origine Fichiers éditeurs autorisés sur une archive ouverte
Licence
Loading...

Dates et versions

hal-02171527 , version 1 (08-07-2020)

Licence

Identifiants

Citer

Corentin Pigot, Guillaume Noirbent, Thanh-Tuan Bui, Sébastien Péralta, Didier Gigmes, et al.. Push-Pull Chromophores Based on the Naphthalene Scaffold: Potential Candidates for Optoelectronic Applications. Materials, 2019, 12 (8), pp.1342. ⟨10.3390/ma12081342⟩. ⟨hal-02171527⟩
121 Consultations
388 Téléchargements

Altmetric

Partager

  • More