Modulation of Reduction Potentials of Bis(pyridinium)alkane Dications through Encapsulation within Cucurbit[7]uril

Nikolai A Tcyrulnikov; Ramkumar Varadharajan; Anastasiia A Tikhomirova; Mahesh Pattabiraman; Vaidhyanathan Ramamurthy; R Marshall Wilson

doi:10.1021/acs.joc.9b01049

Modulation of Reduction Potentials of Bis(pyridinium)alkane Dications through Encapsulation within Cucurbit[7]uril

J Org Chem. 2019 Jul 5;84(13):8759-8765. doi: 10.1021/acs.joc.9b01049. Epub 2019 Jun 26.

Authors

Nikolai A Tcyrulnikov¹, Ramkumar Varadharajan², Anastasiia A Tikhomirova¹, Mahesh Pattabiraman³, Vaidhyanathan Ramamurthy², R Marshall Wilson¹

Affiliations

¹ Center for Photochemical Sciences and Chemistry Department , Bowling Green State University , Bowling Green , Ohio 43403 , United States.
² Department of Chemistry , University of Miami , Coral Gables , Florida 33146 , United States.
³ Department of Chemistry , University of Nebraska , Kearney , Nebraska 68849 , United States.

PMID: 31187624
DOI: 10.1021/acs.joc.9b01049

Abstract

Supramolecular modulation of reduction potentials of two series of bis(pyridinium)alkane salts is described. Study of the encapsulation of bis(pyridinium)alkane guests within the CB[7] cavity revealed the critical influence of the linker length and the position of the heteroatom on the reduction potentials of encapsulated guests. CB[7] complexation of pyridinium salts induced reduction potential changes ranging between +50 and -430 mV. Noncovalent modulation of the electron-accepting ability of organic cations can be utilized in electron-transfer-initiated reactions.