Heptacene: Increased Persistence of a 4n+2 π-Electron Polycyclic Aromatic Hydrocarbon by Oxidation to the 4n π-Electron Dication

被引:54
作者
Einholz, Ralf [1 ]
Bettinger, Holger F. [1 ]
机构
[1] Univ Tubingen, Inst Organ Chem, D-72076 Tubingen, Germany
关键词
aromaticity; dications; heptacene; sulfuric acid; UV; Vis spectroscopy; ESR-SPECTRUM SPREAD; CONFIGURATION-INTERACTION; PENTACENE ANION; GROUND-STATE; ACENES; PHOTOGENERATION; REACTIVITY; STABILITY; HEXACENE;
D O I
10.1002/anie.201209722
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An unexpectedly stable dication: Heptacene (a 4n+2 π-electron compound) is so highly reactive that it cannot be isolated. Its dication (a 4n π-electron compound) can be obtained from heptacene dimers/oligomers in sulfuric acid at room temperature and can be kept for more than one year in the absence of oxygen. (See picture for the UV/Vis-NIR spectra of the dications of tetracene to heptacene.) Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:9818 / 9820
页数:3
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[31]   Time-dependent density functional study of the electronic excited states of polycyclic aromatic hydrocarbon radical ions [J].
Hirata, S ;
Head-Gordon, M ;
Szczepanski, J ;
Vala, M .
JOURNAL OF PHYSICAL CHEMISTRY A, 2003, 107 (24) :4940-4951
[32]   Direct configuration interaction and multiconfigurational self-consistent-field method for multiple active spaces with variable occupations. I. Method [J].
Ivanic, J .
JOURNAL OF CHEMICAL PHYSICS, 2003, 119 (18) :9364-9376
[33]  
MAKELA R, 1984, FINN CHEM LETT, P66
[34]  
Marschalk C., 1941, B SOC CHIM FR II-CH, V8, P354
[35]  
Marschalk Ch., 1943, B SOC CHIM, V10, P511
[36]  
Mondal R, 2008, J PHYS CHEM B, V112, P11, DOI [10.1021/jp076738l, 10.1021/jp0767381]
[37]   Revisiting the stability of hexacenes [J].
Mondal, Rajib ;
Adhikari, Ravi M. ;
Shah, Bipin K. ;
Neckers, Douglas C. .
ORGANIC LETTERS, 2007, 9 (13) :2505-2508
[38]   Photogeneration of heptacene in a polymer matrix [J].
Mondal, Rajib ;
Shah, Bipin K. ;
Neckers, Douglas C. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (30) :9612-9613
[39]   Synthesis, Stability, and Photochemistry of Pentacene, Hexacene, and Heptacene: A Matrix Isolation Study [J].
Mondal, Rajib ;
Toenshoff, Christina ;
Khon, Dmitriy ;
Neckers, Douglas C. ;
Bettinger, Holger F. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (40) :14281-14289
[40]   A spectroscopy oriented configuration interaction procedure [J].
Neese, F .
JOURNAL OF CHEMICAL PHYSICS, 2003, 119 (18) :9428-9443