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
JournalThe Journal of organic chemistry
Volume84
Issue number13
DOIs
StatePublished - Jul 5 2019

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Alkanes
Encapsulation
Modulation
Salts
Electrons
Complexation
Cations
cucurbit(7)uril

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Modulation of Reduction Potentials of Bis(pyridinium)alkane Dications through Encapsulation within Cucurbit[7]uril. / Tcyrulnikov, Nikolai A.; Varadharajan, Ramkumar; Tikhomirova, Anastasiia A.; Pattabiraman, Mahesh; Ramamurthy, Vaidhyanathan; Wilson, R. Marshall.

In: The Journal of organic chemistry, Vol. 84, No. 13, 05.07.2019, p. 8759-8765.

Research output: Contribution to journalArticle

Tcyrulnikov, Nikolai A. ; Varadharajan, Ramkumar ; Tikhomirova, Anastasiia A. ; Pattabiraman, Mahesh ; Ramamurthy, Vaidhyanathan ; Wilson, R. Marshall. / Modulation of Reduction Potentials of Bis(pyridinium)alkane Dications through Encapsulation within Cucurbit[7]uril. In: The Journal of organic chemistry. 2019 ; Vol. 84, No. 13. pp. 8759-8765.
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