The Most Stable and Fully Characterized Functionalized Heptacene

被引:216
作者
Chun, Doris [1 ,2 ]
Cheng, Yang [1 ]
Wudl, Fred [1 ]
机构
[1] Univ Calif Santa Barbara, Dept Chem & Biochem 9510, Santa Barbara, CA 93106 USA
[2] Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
关键词
arynes; heptacenes; pericyclic reaction; polycycles; semiconductors;
D O I
10.1002/anie.200803345
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) Lucky seven: Crystals of heptacene, which consists of seven linearly fused benzene rings, remain stable for at least 21 days in mineral oil and 24 h in degassed solution when the oligoacene is functionalized with phenyl and triisopropylsilylethynyl groups (see scheme). The right combination of functionalities makes this seven-ring system the most stable functionalized heptacene synthesized to date. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:8380 / 8385
页数:6
相关论文
共 20 条
[1]  
[Anonymous], 1999, SAINT SOFTW US GUID
[2]  
[Anonymous], 1999, SMART SOFTW US GUID
[3]   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
[4]   A road map to stable, soluble, easily crystallized pentacene derivatives [J].
Anthony, JE ;
Eaton, DL ;
Parkin, SR .
ORGANIC LETTERS, 2002, 4 (01) :15-18
[5]   The larger acenes: Versatile organic semiconductors [J].
Anthony, John E. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (03) :452-483
[6]   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
[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]   Oligoacenes: Theoretical prediction of open-shell singlet diradical ground states (vol 126, pg 7416, 2004) [J].
Bendikov, M ;
Duong, HM ;
Starkey, K ;
Houk, KN ;
Carter, EA ;
Wudl, F .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (33) :10493-10493
[9]   The influence of side chains on the structures and properties of functionalized pentacenes [J].
Chen, Jihua ;
Subramanian, Sankar ;
Parkin, Sean R. ;
Siegler, Maxime ;
Gallup, Kaitlin ;
Haughn, Chelsea ;
Martin, David C. ;
Anthony, John E. .
JOURNAL OF MATERIALS CHEMISTRY, 2008, 18 (17) :1961-1969
[10]  
Faraday M, 1825, PHIL T, V115, P440