Zwitterionic [4]helicene: a water-soluble and reversible pH-triggered ECD/CPL chiroptical switch in the UV and red spectral regions

Simon Pascal (1) , Céline Besnard (1) , Francesco Zinna (2) , Lorenzo Di Bari (2) , Boris Le Guennic (3) , Denis Jacquemin (4, 5) , Jérôme Lacour (1)

1 UNIGE - Université de Genève = University of Geneva
2 University of Pisa - Università di Pisa
3 ISCR - Institut des Sciences Chimiques de Rennes
4 IUF - Institut Universitaire de France
5 CEISAM - Chimie Et Interdisciplinarité : Synthèse, Analyse, Modélisation

The chiroptical switching properties of a readily accessible and water-soluble diaza [4]helicene are disclosed. This zwitterionic dye displays pH-dependent absorption and emission properties and this enables a reversible turn on/off of electronic circular dichroism at 300 nm and of circularly polarized luminescence in the red region upon protonation/deprotonation.

Domains: Chemical Sciences; Organic chemistry

Simon Pascal, Céline Besnard, Francesco Zinna, Lorenzo Di Bari, Boris Le Guennic, et al.. Zwitterionic [4]helicene: a water-soluble and reversible pH-triggered ECD/CPL chiroptical switch in the UV and red spectral regions. Organic & Biomolecular Chemistry, 2016, 14 (20), pp.4590-4594. ⟨10.1039/c6ob00752j⟩. ⟨hal-01319873⟩