Functionalized higher acenes: Hexacene and heptacene

被引:397
作者
Payne, MM [1 ]
Parkin, SR [1 ]
Anthony, JE [1 ]
机构
[1] Univ Kentucky, Dept Chem, Lexington, KY 40506 USA
关键词
D O I
10.1021/ja051798v
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We have extended our functionalization strategy for pentacene to the higher acenes hexacene and heptacene. Provided a large enough alkyne substituent is used, these large aromatic rods are both stable and soluble and can be characterized spectroscopically as well as by single-crystal X-ray diffraction. Copyright © 2005 American Chemical Society.
引用
收藏
页码:8028 / 8029
页数:2
相关论文
共 20 条
[1]   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
[2]   A road map to stable, soluble, easily crystallized pentacene derivatives [J].
Anthony, JE ;
Eaton, DL ;
Parkin, SR .
ORGANIC LETTERS, 2002, 4 (01) :15-18
[3]   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
[4]   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
[5]   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
[6]   CRYSTAL STRUCTURE OF HEXACENE, AND A REVISION OF CRYSTALLOGRAPHIC DATA FOR TETRACENE AND PENTACENE [J].
CAMPBELL, RB ;
TROTTER, J ;
MONTEATH.J .
ACTA CRYSTALLOGRAPHICA, 1962, 15 (03) :289-&
[7]   A new method for the synthesis of hexacene (aromatic hydrocarbons, XXXIV. Announcement). [J].
Clar, E .
BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1942, 75 :1283-1287
[8]  
Clar E., 1939, CHEM BER, V72, P2137
[9]   Efficient synthesis of a novel, twisted and stable, electroluminescent "Twistacene" [J].
Duong, HM ;
Bendikov, M ;
Steiger, D ;
Zhang, QC ;
Sonmez, G ;
Yamada, J ;
Wudl, F .
ORGANIC LETTERS, 2003, 5 (23) :4433-4436
[10]   Polyacene and cyclacene geometries and electronic structures: Bond equalization, vanishing band gaps, and triplet ground states contrast with polyacetylene [J].
Houk, KN ;
Lee, PS ;
Nendel, M .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (16) :5517-5521