Syntheses of soluble, π-stacking tetracene derivatives

被引：145
作者：
Chen, ZH [1 ]
Muller, P [1 ]
Swager, TM [1 ]
机构：
[1] MIT, Dept Chem, Cambridge, MA 02139 USA
来源：
ORGANIC LETTERS | 2006年 / 8卷 / 02期
关键词：
D O I：
10.1021/ol0526468
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The syntheses of a series of fluorine- and alkyl/alkoxy-functionalized tetracenes are reported. These functional groups are found to improve the solubility in common organic solvents and tune molecular arrangement in solids. The crystal packing, electrochemical behavior, and UV-vis absorbance spectroscopy of these materials are discussed.
引用
收藏
页码：273 / 276
页数：4
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共 45 条
  • [1] Functionalized pentacene: Improved electronic properties from control of solid-state order
    Anthony, JE
    Brooks, JS
    Eaton, DL
    Parkin, SR
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (38) : 9482 - 9483
  • [2] A road map to stable, soluble, easily crystallized pentacene derivatives
    Anthony, JE
    Eaton, DL
    Parkin, SR
    [J]. ORGANIC LETTERS, 2002, 4 (01) : 15 - 18
  • [3] BABEL A, 1998, J AM CHEM SOC, V120, P664
  • [4] Tetrathiafulvalenes, oligoacenenes, and their buckminsterfullerene derivatives: The brick and mortar of organic electronics
    Bendikov, M
    Wudl, F
    Perepichka, DF
    [J]. CHEMICAL REVIEWS, 2004, 104 (11) : 4891 - 4945
  • [5] Using NBS as a mild bromination reagent for polyalkoxyaromatic systems
    Bloomer, JL
    Zheng, W
    [J]. SYNTHETIC COMMUNICATIONS, 1998, 28 (11) : 2087 - 2095
  • [6] Organic semiconductors:: A theoretical characterization of the basic parameters governing charge transport
    Brédas, JL
    Calbert, JP
    da Silva, DA
    Cornil, J
    [J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2002, 99 (09) : 5804 - 5809
  • [7] Charge-transfer and energy-transfer processes in π-conjugated oligomers and polymers:: A molecular picture
    Brédas, JL
    Beljonne, D
    Coropceanu, V
    Cornil, J
    [J]. CHEMICAL REVIEWS, 2004, 104 (11) : 4971 - 5003
  • [8] Synthesis and mesomorphic behavior of a donor-acceptor-type hexaazatriphenylene
    Chang, TH
    Wu, BR
    Chiang, MY
    Liao, SC
    Ong, CW
    Hsu, HF
    Lin, SY
    [J]. ORGANIC LETTERS, 2005, 7 (19) : 4075 - 4078
  • [9] High electron mobility and ambipolar transport in organic thin-film transistors based on a π-stacking quinoidal terthiophene
    Chesterfield, RJ
    Newman, CR
    Pappenfus, TM
    Ewbank, PC
    Haukaas, MH
    Mann, KR
    Miller, LL
    Frisbie, CD
    [J]. ADVANCED MATERIALS, 2003, 15 (15) : 1278 - +
  • [10] Partial fluorination overcomes herringbone crystal packing in small polycyclic aromatics
    Cho, DM
    Parkin, SR
    Watson, MD
    [J]. ORGANIC LETTERS, 2005, 7 (06) : 1067 - 1068
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