Electron-Accepting 6,12-Diethynylindeno[1,2-b]fluorenes: Synthesis, Crystal Structures, and Photophysical Properties

被引:144
作者
Chase, Daniel T. [1 ,2 ]
Fix, Aaron G. [1 ,2 ]
Rose, Bradley D. [1 ,2 ]
Weber, Christopher D. [1 ,2 ]
Nobusue, Shunpei [1 ,2 ]
Stockwell, Chelsea E. [1 ,2 ]
Zakharov, Lev N. [1 ,2 ]
Lonergan, Mark C. [1 ,2 ]
Haley, Michael M. [1 ,2 ]
机构
[1] Univ Oregon, Dept Chem, Eugene, OR 97403 USA
[2] Univ Oregon, Inst Mat Sci, Eugene, OR 97403 USA
基金
美国国家科学基金会;
关键词
aromaticity; electron acceptors; hydrocarbons; polycycles; THIN-FILM TRANSISTORS; HIGH-PERFORMANCE; ORGANIC SEMICONDUCTORS; DERIVATIVES; DENSITY; ABSORPTION; PENTACENE; SPECTRA; ACENES; STATE;
D O I
10.1002/anie.201104797
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Acceptance is good! 2,8-Disubstituted indeno[1,2-b]fluorenes (see structure; TIPS=triisopropylsilyl) were synthesized and characterized. Electrochemical, optical, and computational data indicate that these electron-accepting hydrocarbons possess low-lying HOMO and LUMO energies, and gap energies that are comparable to common organic n-type semiconducting materials. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:11103 / 11106
页数:4
相关论文
共 39 条
[31]   AB-INITIO CALCULATION OF VIBRATIONAL ABSORPTION AND CIRCULAR-DICHROISM SPECTRA USING DENSITY-FUNCTIONAL FORCE-FIELDS [J].
STEPHENS, PJ ;
DEVLIN, FJ ;
CHABALOWSKI, CF ;
FRISCH, MJ .
JOURNAL OF PHYSICAL CHEMISTRY, 1994, 98 (45) :11623-11627
[32]   Air-stable, solution-processable n-channel and ambipolar semiconductors for thin-film transistors based on the indenofluorenebis(dicyanovinylene) core [J].
Usta, Hakan ;
Facchetti, Antonio ;
Marks, Tobin J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (27) :8580-+
[33]   Design, Synthesis, and Characterization of Ladder-Type Molecules and Polymers. Air-Stable, Solution-Processable n-Channel and Ambipolar Semiconductors for Thin-Film Transistors via Experiment and Theory [J].
Usta, Hakan ;
Risko, Chad ;
Wang, Zhiming ;
Huang, Hui ;
Deliomeroglu, Murat K. ;
Zhukhovitskiy, Aleksandr ;
Facchetti, Antonio ;
Marks, Tobin J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (15) :5586-5608
[34]  
Zerubba U.L., 2009, J. Am. Chem. Soc, V131, P2796
[35]  
Zerubba U.L., 2010, J. Am. Chem. Soc, V132, P11012
[36]   Intramolecular Reductive Double Cyclization of o,o′-Bis(arylcarbonyl)-diphenylacetylenes: Synthesis of Ladder π-Conjugated Skeletons [J].
Zhang, Hongyu ;
Karasawa, Takashi ;
Yamada, Hiroshi ;
Wakamiya, Atsushi ;
Yamaguchi, Shigehiro .
ORGANIC LETTERS, 2009, 11 (14) :3076-3079
[37]   Indacenodithiophene Semiconducting Polymers for High-Performance, Air-Stable Transistors [J].
Zhang, Weimin ;
Smith, Jeremy ;
Watkins, Scott E. ;
Gysel, Roman ;
McGehee, Michael ;
Salleo, Alberto ;
Kirkpatrick, James ;
Ashraf, Shahid ;
Anthopoulos, Thomas ;
Heeney, Martin ;
McCulloch, Iain .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (33) :11437-11439
[38]   Systematic Improvement in Charge Carrier Mobility of Air Stable Triarylamine Copolymers [J].
Zhang, Weimin ;
Smith, Jeremy ;
Hamilton, Rick ;
Heeney, Martin ;
Kirkpatrick, James ;
Song, Kigook ;
Watkins, Scott E. ;
Anthopoulos, Thomas ;
McCulloch, Iain .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (31) :10814-+
[39]   SYNTHESIS OF DIACETYLENE MACROCYCLES DERIVED FROM 1,2-DIETHYNYLBENZENE DERIVATIVES - STRUCTURE AND REACTIVITY OF THE STRAINED CYCLIC DIMER [J].
ZHOU, Q ;
CARROLL, PJ ;
SWAGER, TM .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (06) :1294-1301