Beyond Pentacenes: Synthesis and Properties of Higher Acenes

被引:43
作者
Toenshoff, Christina [1 ]
Bettinger, Holger F. [1 ]
机构
[1] Univ Tubingen, Inst Organ Chem, D-72076 Tubingen, Germany
来源
POLYARENES I | 2014年 / 349卷
关键词
Acenes; Alternant hydrocarbon; Polymer; Spectroscopy; Synthesis; AROMATIC-HYDROCARBONS; ORGANIC SEMICONDUCTORS; POLYNUCLEAR AROMATICS; PHOTOELECTRON-SPECTRA; SOLUBLE HEXACENES; CRYSTAL-STRUCTURE; CHARGE-TRANSPORT; ALPHA-DIKETONES; HEPTACENE; DERIVATIVES;
D O I
10.1007/128_2013_437
中图分类号
O65 [分析化学];
学科分类号
070302 ; 081704 ;
摘要
Acenes consist of linearly annulated benzene rings. Their reactivity increases quickly with increasing chain length. Therefore acenes longer than pentacene are very sensitive towards oxygen in the presence of light and thus these molecules have not been well studied or have remained elusive in spite of synthetic efforts dating back to the 1930s. This review gives an historical account of the development of the chemistry of acenes larger than pentacene and summarizes the recent progress in the field including strategies for stabilization of higher acenes up to nonacene.
引用
收藏
页码:1 / 30
页数:30
相关论文
共 61 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]  
[Anonymous], 1986, THESIS U CALIFORNIA
[4]   Functionalized pentacene: Improved electronic properties from control of solid-state order [J].
Anthony, JE ;
Brooks, JS ;
Eaton, DL ;
Parkin, SR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (38) :9482-9483
[5]   The larger acenes: Versatile organic semiconductors [J].
Anthony, John E. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (03) :452-483
[6]   Functionalized acenes and heteroacenes for organic electronics [J].
Anthony, John E. .
CHEMICAL REVIEWS, 2006, 106 (12) :5028-5048
[7]   BEHAVIOR OF FUSED-RING AROMATIC HYDROCARBONS AT VERY HIGH PRESSURE [J].
AUST, RB ;
DRICKAMER, HG ;
BENTLEY, WH .
JOURNAL OF CHEMICAL PHYSICS, 1964, 41 (06) :1856-&
[8]   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
[9]   Tetrathiafulvalenes, oligoacenenes, and their buckminsterfullerene derivatives: The brick and mortar of organic electronics [J].
Bendikov, M ;
Wudl, F ;
Perepichka, DF .
CHEMICAL REVIEWS, 2004, 104 (11) :4891-4945
[10]   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