Synthesis and cofacial π-stacked packing arrangement of 6,13-bis(alkylthio)pentacene

被引：86
作者：
Kobayashi, Kenji
Shimaoka, Reishi
Kawahata, Masatoshi
Yamanaka, Masamichi
Yamaguchi, Kentaro
机构：
[1] Shizuoka Univ, Fac Sci, Dept Chem, Suruga Ku, Shizuoka 4228529, Japan
[2] Tokushima Bunri Univ, Fac Pharmaceut Sci, Sanuki, Kagawa 7692193, Japan
来源：
ORGANIC LETTERS | 2006年 / 8卷 / 11期
关键词：
D O I：
10.1021/ol060679x
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
[graphics] 6,13-Bis(alkylthio)pentacenes directed toward organic field-effect transistors (OFETs) were synthesized by the ZnI2-mediated reaction of trans-6,13- dihydroxy-6,13-dihydropentacene with alkylthiols, followed by the dehydrogenative aromatization of the resulting trans-6,13-bis(alkylthio)6,13- dihydropentacenes with p-chloranil. The X-ray crystallographic analysis of 6,13-bis(methylthio)pentacene reveals that this compound is arranged as a result of cofacial pi-stacking with S-S and S-pi interactions.
引用
收藏
页码：2385 / 2388
页数：4
相关论文
共 52 条
[11]  
Facchetti A, 2000, ANGEW CHEM INT EDIT, V39, P4547, DOI 10.1002/1521-3773(20001215)39:24<4547::AID-ANIE4547>3.0.CO
[12]  
2-J
[13]   Structural characterization of a pentacene monolayer on an amorphous SiO2 substrate with grazing incidence X-ray diffraction [J].
Fritz, SE ;
Martin, SM ;
Frisbie, CD ;
Ward, MD ;
Toney, MF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (13) :4084-4085
[14]   Elastic cycles as flexible hosts: How tubes built by cyclic chalcogenaalkynes individually host their guests [J].
Gleiter, R ;
Werz, DB .
CHEMISTRY LETTERS, 2005, 34 (02) :126-131
[15]   DIRECT SYNTHESIS OF THIOETHERS FROM THIOLS AND ALCOHOLS [J].
GUINDON, Y ;
FRENETTE, R ;
FORTIN, R ;
ROKACH, J .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (08) :1357-1359
[16]  
Holmes D, 1999, CHEM-EUR J, V5, P3399, DOI 10.1002/(SICI)1521-3765(19991105)5:11<3399::AID-CHEM3399>3.0.CO
[17]  
2-V
[18]   Preparation and characterization of π-stacking quinodimethane oligothiophenes.: Predicting semiconductor behavior and bandwidths from crystal structures and molecular orbital calculations [J].
Janzen, DE ;
Burand, MW ;
Ewbank, PC ;
Pappenfus, TM ;
Higuchi, H ;
da Silva, DA ;
Young, VG ;
Brédas, JL ;
Mann, KR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (46) :15295-15308
[19]   Effect of impurities on the mobility of single crystal pentacene [J].
Jurchescu, OD ;
Baas, J ;
Palstra, TTM .
APPLIED PHYSICS LETTERS, 2004, 84 (16) :3061-3063
[20]   Synthetic chemistry for ultrapure, processable, and high-mobility organic transistor semiconductors [J].
Katz, HE ;
Bao, ZN ;
Gilat, SL .
ACCOUNTS OF CHEMICAL RESEARCH, 2001, 34 (05) :359-369
123456