Circularly-Polarized Electrochemiluminescence from a Chiral Bispyrene Organic Macrocycle

Francesco Zinna; Silvia Voci; Lorenzo Arrico; Elodie Brun; Alexandre Homberg; Laurent Bouffier; Tiziana Funaioli; Jérôme Lacour; Neso Sojic; Lorenzo Di Bari

doi:10.1002/anie.201901303

Circularly-Polarized Electrochemiluminescence from a Chiral Bispyrene Organic Macrocycle

Angew Chem Int Ed Engl. 2019 May 20;58(21):6952-6956. doi: 10.1002/anie.201901303. Epub 2019 Apr 17.

Authors

Affiliations

¹ Dipartimento di Chimica e Chimica Industriale, University of Pisa, via G. Moruzzi 13, 56124, Pisa, Italy.
² Department of Organic Chemistry, University of Geneva, Quai Ernest Ansermet 30, 1211, Geneva 4, Switzerland.
³ Univ. Bordeaux, Bordeaux INP, CNRS, Institut des Sciences Moléculaires, UMR 5255, 16 avenue Pey-Berland, 33607, Pessac, France.

PMID: 30916870
DOI: 10.1002/anie.201901303

Abstract

The first observation of circular polarization of electrochemiluminescence (ECL) from a purely organic derivative is reported. A bispyrene scaffold mounted on a constrained polyether macrocycle displaying intense excimer fluorescence and highly circularly-polarized (CP) photoluminescence has been selected for this purpose. The compound displays an ECL dissymmetry factor of about |8×10^-3 |, which is in good agreement with the corresponding photoluminescence value. This observation is the first step towards the molecular engineering of tailored dyes that can act as both ECL and CP-ECL reporters for (bio)analysis by bringing a new level of information when dealing with chiral environments. Additionally, it provides an extra dimension to the ECL phenomenon and opens the way to chiral detection and discrimination.

Keywords: circularly polarized luminescence; electrochemiluminescence; excimer fluorescence; pyrene.

Abstract

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