Stable aromatic dianion in water

Elijah Shirman, Alona Ustinov, Netanel Ben-Shitrit, Haim Weissman, Mark A. Iron, Revital Cohen, Boris Rybtchinski

Research output: Contribution to journalArticle

70 Citations (Scopus)

Abstract

Perylene diimide (PDI) bearing polyethylene glycol substituents at the imide positions was reduced in water with sodium dithionite to produce an aromatic dianion. The latter is stable for months in deoxygenated aqueous solutions, in contrast to all known aromatic dianions which readily react with water. Such stability is due to extensive electron derealization and the aromatic character of the dianion, as evidenced by spectroscopic and theoretical studies. The dianion reacts with oxygen to restore the parent neutral compound, which can be reduced again in an inert atmosphere with sodium dithionite to give the dianion. Such reversible charging renders PDIs useful for controlled electron storage and release in aqueous media. Simple preparation of the dianion, reversible charging, high photoredox power, and stability in water can lead to development of new photofunctional and electron transfer systems in the aqueous phase.

Original languageEnglish
Pages (from-to)8855-8858
Number of pages4
JournalJournal of Physical Chemistry B
Volume112
Issue number30
DOIs
Publication statusPublished - Jul 31 2008

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Dithionite
charging
Electrons
Water
Bearings (structural)
Perylene
Sodium
sodium
water
Imides
inert atmosphere
imides
Polyethylene glycols
glycols
polyethylenes
electron transfer
electrons
Oxygen
aqueous solutions
preparation

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry

Cite this

Shirman, E., Ustinov, A., Ben-Shitrit, N., Weissman, H., Iron, M. A., Cohen, R., & Rybtchinski, B. (2008). Stable aromatic dianion in water. Journal of Physical Chemistry B, 112(30), 8855-8858. https://doi.org/10.1021/jp8029743

Stable aromatic dianion in water. / Shirman, Elijah; Ustinov, Alona; Ben-Shitrit, Netanel; Weissman, Haim; Iron, Mark A.; Cohen, Revital; Rybtchinski, Boris.

In: Journal of Physical Chemistry B, Vol. 112, No. 30, 31.07.2008, p. 8855-8858.

Research output: Contribution to journalArticle

Shirman, E, Ustinov, A, Ben-Shitrit, N, Weissman, H, Iron, MA, Cohen, R & Rybtchinski, B 2008, 'Stable aromatic dianion in water', Journal of Physical Chemistry B, vol. 112, no. 30, pp. 8855-8858. https://doi.org/10.1021/jp8029743
Shirman E, Ustinov A, Ben-Shitrit N, Weissman H, Iron MA, Cohen R et al. Stable aromatic dianion in water. Journal of Physical Chemistry B. 2008 Jul 31;112(30):8855-8858. https://doi.org/10.1021/jp8029743
Shirman, Elijah ; Ustinov, Alona ; Ben-Shitrit, Netanel ; Weissman, Haim ; Iron, Mark A. ; Cohen, Revital ; Rybtchinski, Boris. / Stable aromatic dianion in water. In: Journal of Physical Chemistry B. 2008 ; Vol. 112, No. 30. pp. 8855-8858.
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