From benzyl to fluorenyl: enhancing photostability and modulating optoelectronic properties of <i>para</i> -azaquinodimethanes
Herein, we report synthesis and the characterization of the first fluorenyl-flanked <i>para</i>-azaquinodimethane (F-AQM), which exhibits markedly improved photostability, a pronounced bathochromic shift in absorption, and a reduced optical bandgap compared to its benzyl-flanked analogue (AQM1). Single-crystal X-ray diffraction and theoretical calculations reveal a bent quinoidal core with twisted fluorenyl units, highlighting F-AQM as a promising quinoidal semiconductor building block.
Authors
- Marwan Kobeissi (ORCID: https://orcid.org/0000-0002-1872-9890)
- Bruno Schmaltz (ORCID: https://orcid.org/0000-0001-8298-9489)
- Walaa Zwaihed
- François Maurel
- Guido Pauli
- Clement Cabanetos
- Magali Allain
Institutions
- Université de Tours (FR)
- Centre National de la Recherche Scientifique (FR)
- Lebanese University (LB)
- Université Paris Cité (FR)
- University of Illinois Chicago (US)
- Interfaces Traitements Organisation et Dynamique des Systèmes (FR)
- Institut des Sciences et Technologies Moléculaires d'Angers (FR)
Publication Details
- Journal
- Chemical Communications
- Published
- 2026-01-01
- DOI
- https://doi.org/10.1039/d5cc06382e
- Primary Topic
- Synthesis and Properties of Aromatic Compounds
- Type
- article
- Field-Weighted Citation Impact
- 0.00