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Open AccessArticle

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

1
Aix Marseille Univ, CNRS, ICR UMR7273, F-13397 Marseille, France
2
Laboratoire de Physicochimie des Polymères et des Interfaces (LPPI), Université de Cergy Pontoise, 5 mail Gay Lussac, F-95000 Neuville-sur-Oise, France
*
Authors to whom correspondence should be addressed.
Materials 2019, 12(8), 1342; https://doi.org/10.3390/ma12081342
Received: 5 April 2019 / Revised: 19 April 2019 / Accepted: 22 April 2019 / Published: 24 April 2019
(This article belongs to the Special Issue Advances and Challenges in Organic Electronics)
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. View Full-Text
Keywords: push-pull dyes; chromophore; naphthalene; solvatochromism push-pull dyes; chromophore; naphthalene; solvatochromism
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MDPI and ACS Style

Pigot, C.; Noirbent, G.; Bui, T.-T.; Péralta, S.; Gigmes, D.; Nechab, M.; Dumur, F. Push-Pull Chromophores Based on the Naphthalene Scaffold: Potential Candidates for Optoelectronic Applications. Materials 2019, 12, 1342.

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