Tuning the solid-state emission of small push-pull dipolar dyes to the far-red through variation of the electron-acceptor group

Sébastien Redon (1) , Gwenaelle Eucat (2) , Martin Ipuy (3) , Erwann Jeanneau (4) , Isabelle Gautier-Luneau (2) , Alain Ibanez (2) , Chantal Andraud (3) , Yann Bretonnière (3)

1 ICR - Institut de Chimie Radicalaire
2 NEEL - OPTIMA - Optique et Matériaux
3 LC - Laboratoire de Chimie - UMR5182
4 UCBL - Université Claude Bernard Lyon 1

Series of solid-state emitters based on the D-π-A dipolar structure and featuring various electron-donor and electron-acceptor groups were designed, and their spectroscopic properties studied. From weak emission in dilute solutions, intense emissions in aggregated state (AIE) and in the crystalline state were obtained. Analysis in light of crystal structures obtained by X-ray diffraction revealed specific crystal packing and presence of long chain of emitting aggregates. This simple molecular engineering around the D-π-A dipolar structure provides easy access to a wide range of effective solid-state emitters allowing modulation of emission wavelengths up to the near infrared (λem reaching 735 and 768 nm for compound 2f and 3f bearing the strongest electron-withdrawing group).

Keywords: 2(5H)-furanone rings; Push-pull dyes; Organic dyes; Near-infrared; Aggregation-induced emission; Solid-state fluorescence

Domains: Chemical Sciences; Organic chemistry; Chemical Sciences; Material chemistry; Chemical Sciences; Cristallography

Sébastien Redon, Gwenaelle Eucat, Martin Ipuy, Erwann Jeanneau, Isabelle Gautier-Luneau, et al.. Tuning the solid-state emission of small push-pull dipolar dyes to the far-red through variation of the electron-acceptor group. Dyes and Pigments, 2018, 156, pp.116-132. ⟨10.1016/j.dyepig.2018.03.049⟩. ⟨hal-01856313⟩