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

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2013年 / 52卷 / 37期

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

页码：9818 / 9820

页数：3

共 50 条

[1] THE RADICAL IONS OF HEXACENE [J].

ANGLIKER, H ;

GERSON, F ;

LOPEZ, J ;

WIRZ, J .

CHEMICAL PHYSICS LETTERS, 1981, 81 (02) :242-246

[2] ELECTRONIC-SPECTRA OF HEXACENE IN SOLUTION (GROUND-STATE, TRIPLET-STATE, DICATION AND DIANION) [J].

ANGLIKER, H ;

ROMMEL, E ;

WIRZ, J .

CHEMICAL PHYSICS LETTERS, 1982, 87 (02) :208-212

[3] Hydrogen-protected acenes [J].

Athans, Andreas J. ;

Briggs, Jonathan B. ;

Jia, Wenling ;

Miller, Glen P. .

JOURNAL OF MATERIALS CHEMISTRY, 2007, 17 (25) :2636-2641

[4] CYCLIC DIENES .11. NEW SYNTHESES OF HEXACENE AND HEPTACENE [J].

BAILEY, WJ ;

LIAO, CW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (04) :992-993

[5] SEMICONDUCTOR-LIKE STRUCTURE OF INFINITE LINEAR POLYACENE [J].

BALDO, M ;

PICCITTO, G ;

PUCCI, R ;

TOMASELLO, P .

PHYSICS LETTERS A, 1983, 95 (3-4) :201-203

[6]

BALK P, 1957, RECL TRAV CHIM PAY B, V76, P813

[7] Oligoacenes: Theoretical prediction of open-shell singlet diradical ground states [J].

Bendikov, M ;

Duong, HM ;

Starkey, K ;

Houk, KN ;

Carter, EA ;

Wudl, F .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (24) :7416-7417

[8] Stable photoinduced charge separation in heptacene [J].

Bettinger, Holger F. ;

Mondal, Rajib ;

Neckers, Douglas C. .

CHEMICAL COMMUNICATIONS, 2007, (48) :5209-5211

[9] Electronic structure of higher acenes and polyacene: The perspective developed by theoretical analyses [J].

Bettinger, Holger F. .

PURE AND APPLIED CHEMISTRY, 2010, 82 (04) :905-915

[10] DIELS-ALDER REACTIVITY OF POLYCYCLIC AROMATIC-HYDROCARBONS .1. ACENES AND BENZOLOGS [J].

BIERMANN, D ;

SCHMIDT, W .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (09) :3163-3173

← 1 2 3 4 5 →