Low-LUMO Pyrene-Fused Azaacenes

被引:54
作者
More, Sandeep [1 ,3 ,4 ]
Bhosale, Rajesh [3 ,4 ]
Mateo-Alonso, Aurelio [1 ,2 ]
机构
[1] Univ Basque Country UPV EHU, POLYMAT, Donostia San Sebastian 20018, Spain
[2] Basque Fdn Sci, Ikerbasque, Bilbao 48011, Spain
[3] Univ Freiburg, Freiburg Inst Adv Studies FRIAS, Sch Soft Matter Res, D-79104 Freiburg, Germany
[4] Univ Freiburg, Inst Organ Chem & Biochem, D-79104 Freiburg, Germany
关键词
azaacenes; electronic materials; low LUMO; polycyclic aromatic hydrocarbons; pyrene; CHANNEL ORGANIC SEMICONDUCTORS; FIELD-EFFECT TRANSISTORS; THIN-FILM TRANSISTORS; ELECTRONIC-PROPERTIES; BISPHENAZINE DERIVATIVES; CARBON NANOTUBES; LADDER POLYMERS; N-HETEROACENES; MOLECULES; NITROGEN;
D O I
10.1002/chem.201304461
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A series of pyrene-fused azaacenes with four and six linearly fused rings that possess LUMO levels between -3.7 and -4.3 eV is reported. These LUMO values are remarkably lower than those typically observed for pyrene-fused azaacenes, even for systems with sixteen linearly fused rings, and are comparable to those observed for state-of-the-art n-azaacenes.
引用
收藏
页码:10626 / 10631
页数:6
相关论文
共 64 条
[1]  
[Anonymous], 2009, ANGEW CHEM, DOI DOI 10.1002/ANGE.200805152
[2]   Effects of electronegative substitution on the optical and electronic properties of acenes and diazaacenes [J].
Appleton, Anthony Lucas ;
Brombosz, Scott M. ;
Barlow, Stephen ;
Sears, John S. ;
Bredas, Jean-Luc ;
Marder, Seth R. ;
Bunz, Uwe H. F. .
NATURE COMMUNICATIONS, 2010, 1
[3]  
Arnold F. E., 1969, POLYM LETT, V7, P749
[4]   LADDER POLYMERS FROM TETRAAMINODIQUINOXALPYRENE [J].
ARNOLD, FE .
JOURNAL OF POLYMER SCIENCE PART A-1-POLYMER CHEMISTRY, 1970, 8 (08) :2079-&
[5]   Morphology and Photoelectrical Properties of Solution Processable Butylamine-Modified Graphene- and Pyrene-Based Organic Semiconductor [J].
Bon, Silvia Bittolo ;
Valentini, Luca ;
Moustafa, Rasha M. ;
Jradi, Fadi M. ;
Kaafarani, Bilal R. ;
Verdejo, Raquel ;
Lopez-Manchado, Miguel Angel ;
Kenny, Jose M. .
JOURNAL OF PHYSICAL CHEMISTRY C, 2010, 114 (25) :11252-11257
[6]   Controlling the electron-deficiency of self-assembling pyrazine-acenes: a collaborative experimental and theoretical investigation [J].
Brownell, Lacie V. ;
Jang, Kyoungmi ;
Robins, Kathleen A. ;
Tran, Ich C. ;
Heske, Clemens ;
Lee, Dong-Chan .
PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2013, 15 (16) :5967-5974
[7]  
Bunz U. H. F., 2013, ANGEW CHEM, V125, P3898
[8]   Large N-Heteroacenes: New Tricks for Very Old Dogs? [J].
Bunz, Uwe H. F. ;
Engelhart, Jens U. ;
Lindner, Benjamin D. ;
Schaffroth, Manuel .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (14) :3810-3821
[9]   N-Heteroacenes [J].
Bunz, Uwe H. F. .
CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (28) :6780-6789
[10]   Columnar Mesomorphism of Fluorescent Board-Shaped Quinoxalinophenanthrophenazine Derivatives with Donor-Acceptor Structure [J].
Chen, Shuai ;
Read, Farah S. ;
Ahmida, Mohamed ;
Kaafarani, Bilal R. ;
Eichhorn, S. Holger .
ORGANIC LETTERS, 2013, 15 (03) :558-561