Synthesis, Reactivity, and Electronic Properties of 6,6-Dicyanofulvenes

被引:55
作者
Andrew, Trisha L. [1 ]
Cox, Jason R. [1 ]
Swager, Timothy M. [1 ]
机构
[1] MIT, Dept Chem, Cambridge, MA 02139 USA
基金
美国国家科学基金会;
关键词
FIELD-EFFECT TRANSISTORS; THIN-FILM TRANSISTORS; N-CHANNEL; HIGH-PERFORMANCE; BUILDING-BLOCKS; BAND-GAP; SEMICONDUCTORS; DESIGN; MICROSTRUCTURE; DERIVATIVES;
D O I
10.1021/ol102384k
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of 6,6-dicyanofulvene derivatives are synthesized starting from masked, dimeric, or monomeric cyclopentadienones. The reactivities of 6,6-dicyanofulvenes relative to their parent cyclopentadienones are discussed. 6,6-Dicyanofulvenes are capable of undergoing two consecutive, reversible, one-electron reductions and are presented as potential n-type small molecules.
引用
收藏
页码:5302 / 5305
页数:4
相关论文
共 41 条
[31]   A π-stacking terthiophene-based quinodimethane is an n-channel conductor in a thin film transistor [J].
Pappenfus, TM ;
Chesterfield, RJ ;
Frisbie, CD ;
Mann, KR ;
Casado, J ;
Raff, JD ;
Miller, LL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (16) :4184-4185
[32]   Organic field-effect transistors from solution-deposited functionalized acenes with mobilities as high as 1 cm2/V-s [J].
Payne, MM ;
Parkin, SR ;
Anthony, JE ;
Kuo, CC ;
Jackson, TN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (14) :4986-4987
[33]   Core-Fluorinated Perylene Bisimide Dyes: Air Stable n-Channel Organic Semiconductors for Thin Film Transistors with Exceptionally High On-to-Off Current Ratios [J].
Schmidt, Ruediger ;
Ling, Mang Mang ;
Oh, Joon Hak ;
Winkler, Michael ;
Koenemann, Martin ;
Bao, Zhenan ;
Wuerthner, Frank .
ADVANCED MATERIALS, 2007, 19 (21) :3692-3695
[34]   Charge carrier transporting molecular materials and their applications in devices [J].
Shirota, Yasuhiko ;
Kageyama, Hiroshi .
CHEMICAL REVIEWS, 2007, 107 (04) :953-1010
[35]   DESIGN AND APPLICATION OF ELECTRON-TRANSPORTING ORGANIC MATERIALS [J].
STRUKELJ, M ;
PAPADIMITRAKOPOULOS, F ;
MILLER, TM ;
ROTHBERG, LJ .
SCIENCE, 1995, 267 (5206) :1969-1972
[36]   Chromophore fluorination enhances crystallization and stability of soluble anthradithiophene semiconductors [J].
Subramanian, Sankar ;
Park, Sung Kyu ;
Parkin, Sean R. ;
Podzorov, Vitaly ;
Jackson, Thomas N. ;
Anthony, John E. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (09) :2706-+
[37]   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-+
[38]   Synthesis and characterization of electron-deficient and highly soluble (Bis)Indenofluorene building blocks for n-type semiconducting polymers [J].
Usta, Hakan ;
Facchetti, Antonio ;
Marks, Tobin J. .
ORGANIC LETTERS, 2008, 10 (07) :1385-1388
[39]   Visible and Near-infrared Absorbing, Low Band Gap Conjugated Oligomers Based on Cyclopentadieneones [J].
Walker, Wesley ;
Veldman, Brittnee ;
Chiechi, Ryan ;
Patil, Satish ;
Bendikov, Michael ;
Wudl, Fred .
MACROMOLECULES, 2008, 41 (20) :7278-7280
[40]   NOVEL QUINONE-TYPE ACCEPTORS FUSED WITH SULFUR HETEROCYCLES AND THEIR HIGHLY CONDUCTIVE COMPLEXES WITH ELECTRON-DONORS [J].
YAMASHITA, Y ;
SUZUKI, T ;
SAITO, G ;
MUKAI, T .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (19) :1489-1491