On the unexpected stability of the dianion of perylene diimide in water - A computational study

Mark A. Iron, Revital Cohen, Boris Rybtchinski

Research output: Contribution to journalArticle

30 Citations (Scopus)

Abstract

It was recently reported (Shirman, J. Phys. Chem. B, 2008, 112, 8855) that the stable dianion of perylene diimide can be prepared in water. Herein, a computational study (using DFT at the M06-2X/6-31++G* level of theory) of this species is presented. It is shown that this dianion is aromatic and that its reaction with water is highly endergonic. The primary cause for this is the stabilization provided by the enhanced aromaticity of the dianion relative to its neutral counterpart. Comparison with other aromatic dianions is also presented.

Original languageEnglish
Pages (from-to)2047-2056
Number of pages10
JournalJournal of Physical Chemistry A
Volume115
Issue number10
DOIs
Publication statusPublished - Mar 17 2011

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry

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