Indeno[2,1-c]fluorene: A New Electron-Accepting Scaffold for Organic Electronics

被引:120
作者
Fix, Aaron G.
Deal, Parker E.
Vonnegut, Chris L.
Rose, Bradley D.
Zakharov, Lev N.
Haley, Michael M. [1 ]
机构
[1] Univ Oregon, Dept Chem, Eugene, OR 97403 USA
基金
美国国家科学基金会;
关键词
CRYSTAL-STRUCTURES; DERIVATIVES; AMBIPOLAR;
D O I
10.1021/ol400318z
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new class of fully conjugated indenofluorenes has been synthesized and confirmed by solid-state structure analysis. These Indeno[2,1c]fluorene molecules, containing an antiaromatic as-indacene core (in red), possess high electron affinities and show a broad absorption that reaches into the near-IR region of the electromagnetic spectrum. All of the featured compounds reversibly accept up to two electrons. Their electronic properties make this class of compounds attractive for applications in organic electronic devices.
引用
收藏
页码:1362 / 1365
页数:4
相关论文
共 35 条
[1]   Small-Molecule, Nonfullerene Acceptors for Polymer Bulk Heterojunction Organic Photovoltaics [J].
Anthony, John E. .
CHEMISTRY OF MATERIALS, 2011, 23 (03) :583-590
[2]   n-Type Organic Semiconductors in Organic Electronics [J].
Anthony, John E. ;
Facchetti, Antonio ;
Heeney, Martin ;
Marder, Seth R. ;
Zhan, Xiaowei .
ADVANCED MATERIALS, 2010, 22 (34) :3876-3892
[3]   DENSITY-FUNCTIONAL THERMOCHEMISTRY .3. THE ROLE OF EXACT EXCHANGE [J].
BECKE, AD .
JOURNAL OF CHEMICAL PHYSICS, 1993, 98 (07) :5648-5652
[4]   6,12-Diarylindeno[1,2-b]fluorenes: Syntheses, Photophysics, and Ambipolar OFETs [J].
Chase, Daniel T. ;
Fix, Aaron G. ;
Kang, Seok Ju ;
Rose, Bradley D. ;
Weber, Christopher D. ;
Zhong, Yu ;
Zakharov, Lev N. ;
Lonergan, Mark C. ;
Nuckolls, Colin ;
Haley, Michael M. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (25) :10349-10352
[5]   Electron-Accepting 6,12-Diethynylindeno[1,2-b]fluorenes: Synthesis, Crystal Structures, and Photophysical Properties [J].
Chase, Daniel T. ;
Fix, Aaron G. ;
Rose, Bradley D. ;
Weber, Christopher D. ;
Nobusue, Shunpei ;
Stockwell, Chelsea E. ;
Zakharov, Lev N. ;
Lonergan, Mark C. ;
Haley, Michael M. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (47) :11103-11106
[6]   Indeno[1,2-b]fluorenes: Fully Conjugated Antiaromatic Analogues of Acenes [J].
Chase, Daniel T. ;
Rose, Bradley D. ;
McClintock, Sean P. ;
Zakharov, Lev N. ;
Haley, Michael M. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (05) :1127-1130
[7]   Chemical redox agents for organometallic chemistry [J].
Connelly, NG ;
Geiger, WE .
CHEMICAL REVIEWS, 1996, 96 (02) :877-910
[8]   Palladium-Catalyzed Pentannulation of Polycyclic Aromatic Hydrocarbons [J].
Eversloh, Christian Luetke ;
Avlasevich, Yuri ;
Li, Chen ;
Muellen, Klaus .
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (45) :12756-12762
[9]   Indenofluorenes and Derivatives: Syntheses and Emerging Materials Applications [J].
Fix, Aaron G. ;
Chase, Daniel T. ;
Haley, Michael M. .
POLYARENES I, 2014, 349 :159-195
[10]  
Frisch M.J., 2009, All calculations were performed with Gaussian 09