Issue 20, 2016
From the journal:

Organic & Biomolecular Chemistry

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

Simon Pascal, ORCID logo a   Céline Besnard,b   Francesco Zinna,c   Lorenzo Di Bari,c   Boris Le Guennic,d   Denis Jacqueminef  and  Jérôme Lacour*a  

* Corresponding authors

a University of Geneva, Department of Organic Chemistry, quai Ernest Ansermet 30, CH-1211 Geneva 4, Switzerland
E-mail: Jerome.lacour@unige.ch

b Laboratory of Crystallography, University of Geneva, quai Ernest Ansermet 24, CH-1211 Geneva 4, Switzerland

c Università di Pisa, Dipartimento di Chimica e Chimica Industriale, Via G. Moruzzi 13, 56124 Pisa, Italy

d Institut des Sciences Chimiques de Rennes, UMR 6226 CNRS-Université de Rennes 1, 263 avenue du Général Leclerc, 35042 Rennes Cedex, France

e Laboratoire CEISAM, UMR 6230 CNRS, Université de Nantes, 2 rue de la Houssinière, BP 92208, 44322 Nantes Cedex 3, France

f Institut Universitaire de France, 1, rue Descartes, F-75005 Paris Cedex 05, France

Abstract

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.

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

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Article information

DOI
https://doi.org/10.1039/C6OB00752J
Article type
Communication
Submitted
08 Apr 2016
Accepted
22 Apr 2016
First published
25 Apr 2016

Org. Biomol. Chem., 2016,14, 4590-4594

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

S. Pascal, C. Besnard, F. Zinna, L. Di Bari, B. Le Guennic, D. Jacquemin and J. Lacour, Org. Biomol. Chem., 2016, 14, 4590 DOI: 10.1039/C6OB00752J

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