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Issue 29, 2017
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Electrochemical and structural investigation of the interactions between naphthalene diimides and metal cations

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Abstract

The effects of Li+ and Mg2+ on the electrochemical behaviour and photoreduction of N,N′-bis(2,6-diisopropylphenyl)naphthalene diimide (Dipp2NDI) have been investigated using cyclic voltammetry and UV-vis spectroscopy. Strong cation–anion interactions between Li+ or Mg2+ and [Dipp2NDI]2− result in solvent-dependent anodic shifts of the NDI˙−/2− redox couple. In organic solvents of moderate dielectric constant and donor ability, the two, one-electron redox processes typically observed for Dipp2NDI merge into a single, two-electron process. This strong metal cation effect has been leveraged for the photoreduction of Dipp2NDI to [Dipp2NDI]2−via a disproportionation process. Chemical reduction of Dipp2NDI with iPrMgCl has allowed the isolation of Mg2+ complexes of [Dipp2NDI]2−. Single crystal X-ray diffraction was used to determine the structure of a dimeric complex, [(Dipp2NDI)Mg2(THF)3]2, that features strong coordination of Mg2+ by the oxygen atoms of the reduced NDI.

Graphical abstract: Electrochemical and structural investigation of the interactions between naphthalene diimides and metal cations

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Publication details

The article was received on 06 Jun 2017, accepted on 28 Jun 2017 and first published on 28 Jun 2017


Article type: Paper
DOI: 10.1039/C7DT02067H
Citation: Dalton Trans., 2017,46, 9472-9480
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    Electrochemical and structural investigation of the interactions between naphthalene diimides and metal cations

    B. R. Reiner, B. M. Foxman and C. R. Wade, Dalton Trans., 2017, 46, 9472
    DOI: 10.1039/C7DT02067H

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