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

Mark A. Iron; Revital Cohen; Boris Rybtchinski

doi:10.1021/jp1107284

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

Mark A. Iron, Revital Cohen, Boris Rybtchinski

Weizmann Institute of Science

Research output: Contribution to journal › Article › peer-review

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 language	English
Pages (from-to)	2047-2056
Number of pages	10
Journal	Journal of Physical Chemistry A
Volume	115
Issue number	10
DOIs	https://doi.org/10.1021/jp1107284
State	Published - 17 Mar 2011

All Science Journal Classification (ASJC) codes

Physical and Theoretical Chemistry

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10.1021/jp1107284

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title = "On the unexpected stability of the dianion of perylene diimide in water - A computational study",

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.",

author = "Iron, {Mark A.} and Revital Cohen and Boris Rybtchinski",

note = "Israel Science Foundation; Helen and Martin Kimmel Center for Molecular DesignThis work was supported by grants from the Israel Science Foundation and the Helen and Martin Kimmel Center for Molecular Design. B.R. is the incumbent of the Abraham and Jennie Fialkow Career Development Chair.",

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AU - Iron, Mark A.

AU - Cohen, Revital

AU - Rybtchinski, Boris

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AB - 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.

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JO - Journal of Physical Chemistry A

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

Abstract

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