A Bis-Acridinium Macrocycle as Multi-Responsive Receptor and Selective Phase-Transfer Agent of Perylene

Johnny Hu; Jas S Ward; Alain Chaumont; Kari Rissanen; Jean-Marc Vincent; Valérie Heitz; Henri-Pierre Jacquot de Rouville

doi:10.1002/anie.202009212

A Bis-Acridinium Macrocycle as Multi-Responsive Receptor and Selective Phase-Transfer Agent of Perylene

Angew Chem Int Ed Engl. 2020 Dec 14;59(51):23206-23212. doi: 10.1002/anie.202009212. Epub 2020 Oct 6.

Authors

Johnny Hu¹, Jas S Ward², Alain Chaumont³, Kari Rissanen², Jean-Marc Vincent⁴, Valérie Heitz¹, Henri-Pierre Jacquot de Rouville¹

Affiliations

¹ LSAMM, Institut de Chimie de Strasbourg, CNRS UMR 7177, Université de Strasbourg, 4, rue Blaise Pascal, 67000, Strasbourg, France.
² University of Jyvaskyla, Department of Chemistry, P.O. BOX 35, Survontie 9B, 40014, Jyväskylä, Finland.
³ Chimie de la Matière Complexe, CNRS UMR 7140, Université de Strasbourg, 4, rue Blaise Pascal, 67000, Strasbourg, France.
⁴ Institut des Sciences Moléculaires, CNRS UMR 5255, Université de Bordeaux, 351 cours de la Libération, 33405, Talence, France.

PMID: 32881218
DOI: 10.1002/anie.202009212

Abstract

A bis-acridinium cyclophane incorporating switchable acridinium moieties linked by a 3,5-dipyridylanisole spacer was studied as a multi-responsive host for polycyclic aromatic hydrocarbon guests. Complexation of perylene was shown to be the most effective and was characterized in particular by a charge-transfer band as signal output. Effective catch and release of the guest was triggered by both chemical (proton/hydroxide) and redox stimuli. Moreover, the dicationic host was also easily switched between organic and perfluorocarbon phases for applications related to the enrichment of perylene from a mixture of polycyclic aromatic hydrocarbons.

Keywords: acridinium; host-guest chemistry; multi-responsive receptor; perfluorocarbons; phase transfer.