On the Unexpected Stability of the Dianion of Perylene Diimide in Water-A Computational Study

被引：50

作者：

Iron, Mark A. ^{[1
]}

Cohen, Revital ^{[1
]}

Rybtchinski, Boris ^{[2
]}

机构：

[1] Weizmann Inst Sci, Dept Chem Res Support, Computat Chem Unit, IL-76100 Rehovot, Israel

[2] Weizmann Inst Sci, Dept Organ Chem, IL-76100 Rehovot, Israel

来源：

JOURNAL OF PHYSICAL CHEMISTRY A | 2011年 / 115卷 / 10期

基金：

以色列科学基金会;

关键词：

POLARIZABLE CONTINUUM MODEL; STATE PERTURBATION-THEORY; MOLECULAR-ORBITAL METHODS; OXYGEN REDUCTION; DENSITY FUNCTIONALS; EFFICIENT IMPLEMENTATION; BUILDING-BLOCKS; IONIC-SOLUTIONS; RADICAL-ANIONS; BASIS-SETS;

D O I：

10.1021/jp1107284

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

It was recently reported (Shirman, et al. 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.

引用

页码：2047 / 2056

页数：10

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