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Updated: Feb 26, 2026
Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
Electrochemical and structural investigation of the interactions between naphthalene diimides and metal cations
Benjamin R Reiner1, Bruce M Foxman1, Casey R Wade1
1Department of Chemistry, Brandeis University, 415 South St., Waltham, MA, USA. cwade@brandeis.edu.
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.
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