Synthesis, characterization and unusual near-infrared luminescence of 1,1,4,4-tetracyanobutadiene derivatives

Anh Thy Bui (1) , Clotilde Philippe (1) , Maxime Beau (1) , Nicolas Richy (1) , Marie Cordier (1) , Thierry Roisnel (1) , Loïc Lemiègre (1) , Olivier Mongin (1) , Frédéric Paul (1) , Yann Trolez (1)

1 ISCR - Institut des Sciences Chimiques de Rennes

Two 1,1,4,4-tetracyanobutadiene (TCBD) derivatives were prepared by [2+2]cycloaddition-retroelectrocyclization from ynamides bearing either a pyrene (1) or a perylene unit (2). In addition to panchromatic absorptions in 2, in the solid state, both compounds unexpectedly display NIR photoluminescence that could be detected up to about 1350 nm.

Domains: Chemical Sciences

Anh Thy Bui, Clotilde Philippe, Maxime Beau, Nicolas Richy, Marie Cordier, et al.. Synthesis, characterization and unusual near-infrared luminescence of 1,1,4,4-tetracyanobutadiene derivatives. Chemical Communications, 2020, 56 (24), pp.3571-3574. ⟨10.1039/c9cc09560h⟩. ⟨hal-02498790⟩