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

Research output: Contribution to journalArticle

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.

Original languageEnglish (US)
Pages (from-to)8759-8765
Number of pages7
JournalJournal of Organic Chemistry
Volume84
Issue number13
DOIs
StatePublished - Jul 5 2019

ASJC Scopus subject areas

  • Organic Chemistry

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