Systematically Studying the Effect of Fluoride on the Properties of Cyclophanes Bearing Naphthalene Diimide and Dialkoxyaryl Groups

Nicholas A Young; Simon C Drew; Subashani Maniam; Steven J Langford

doi:10.1002/asia.201700459

Systematically Studying the Effect of Fluoride on the Properties of Cyclophanes Bearing Naphthalene Diimide and Dialkoxyaryl Groups

Chem Asian J. 2017 Jul 4;12(13):1668-1675. doi: 10.1002/asia.201700459. Epub 2017 Jun 12.

Authors

Nicholas A Young¹, Simon C Drew², Subashani Maniam¹, Steven J Langford¹

Affiliations

¹ School of Chemistry, Monash University, Wellington Rd, Clayton, Victoria, 3800, Australia.
² Department of Medicine, Royal Melbourne Hospital, The University of Melbourne, Melbourne, Victoria, 3010, Australia.

PMID: 28605160
DOI: 10.1002/asia.201700459

Abstract

Anion-π interactions between the Lewis basic anion fluoride and π-acidic naphthalene diimide was systematically studied in a series of cyclophanes in which the properties are modulated through the influence of a second, electron-rich aromatic unit. The systems and subsequently generated radical anions, upon addition of fluoride, were studied by absorption spectroscopic and EPR techniques. The results infer a modulation as a result of the nature and strength of the π-π interaction in the macrocyclic structure.

Keywords: EPR; anion-pi interactions; fluoride; naphthalene diimide; radicals; sensors.