2,1,3-Benzothiadiazole Dimers: Preparation, Structure, and Transannular Electronic Interactions of syn- and anti-[2.2](4,7)Benzothiadiazolophanes

被引：25
作者：
Watanabe, Motonori [1 ,2 ]
Goto, Kenta [1 ]
Fujitsuka, Mamoru [3 ]
Tojo, Sachiko [3 ]
Majima, Tetsuro [3 ]
Shinmyozu, Teruo [1 ]
机构：
[1] Kyushu Univ, Inst Mat Chem & Engn IMCE, Fukuoka 8128581, Japan
[2] Kyushu Univ, Grad Sch Sci, Dept Chem, Fukuoka 8128581, Japan
[3] Osaka Univ, Inst Sci & Ind Res SANKEN, Osaka 5670047, Japan
来源：
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN | 2010年 / 83卷 / 10期
关键词：
FIELD-EFFECT TRANSISTORS; CATION-RADICALS; THROUGH-SPACE; MACRO RINGS; ABSORPTION-SPECTRA; CRYSTAL-STRUCTURE; SELF-EXCHANGE; PI-COMPLEX; RESONANCE; ENERGY;
D O I：
10.1246/bcsj.20100085
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The cyclophanes comprised of two 2,1,3-benzothiadiazole (BTD) rings, anti- and syn-[2.2](4,7)benzothiadiazolophanes (anti-1 and syn-1), were prepared for the first time. The differences of the physical properties in the overlapping mode of the pi-systems are clearly observed, and syn-1 shows much more significant transannular pi-electronic interactions than anti-1 especially in the redox properties and the stability of the radical anion species.
引用
收藏
页码：1155 / 1161
页数：7
相关论文
共 53 条
  • [1] Synthesis, characterization and FET properties of novel dithiazolylbenzothiadiazole derivatives
    Akhtaruzzaman, M
    Kamata, N
    Nishida, J
    Ando, S
    Tada, H
    Tomura, M
    Yamashita, Y
    [J]. CHEMICAL COMMUNICATIONS, 2005, (25) : 3183 - 3185
  • [2] Synthesis and characterization of novel dipyridylbenzothiadiazole and bisbenzothiadiazole derivatives
    Akhtaruzzaman, M
    Tomura, M
    Nishida, J
    Yamashita, Y
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (09) : 2953 - 2958
  • [3] SIR97:: a new tool for crystal structure determination and refinement
    Altomare, A
    Burla, MC
    Camalli, M
    Cascarano, GL
    Giacovazzo, C
    Guagliardi, A
    Moliterni, AGG
    Polidori, G
    Spagna, R
    [J]. JOURNAL OF APPLIED CRYSTALLOGRAPHY, 1999, 32 : 115 - 119
  • [4] [Anonymous], 1985, TEXSAN CRYST STRUCT
  • [5] FORMATION OF DIMER CATIONS OF AROMATIC HYDROCARBONS
    BADGER, B
    BROCKLEH.B
    [J]. NATURE, 1968, 219 (5151) : 263 - &
  • [6] THE PI-COMPLEX BENZENE ETHYLENE CATION RADICAL
    BALLY, T
    ROTH, K
    STRAUB, R
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (05) : 1639 - 1641
  • [7] BAUERLE P, 1993, J AM CHEM SOC, V115, P10217
  • [8] BAUERLE P, 1993, ANGEW CHEM INT EDIT, V32, P76, DOI 10.1002/anie.199300761
  • [9] DENSITY-FUNCTIONAL THERMOCHEMISTRY .3. THE ROLE OF EXACT EXCHANGE
    BECKE, AD
    [J]. JOURNAL OF CHEMICAL PHYSICS, 1993, 98 (07) : 5648 - 5652
  • [10] LIN-POLY-PARA-XYLYLENE .2. THE CRYSTAL STRUCTURE OF DI-P-XYLYLENE
    BROWN, CJ
    [J]. JOURNAL OF THE CHEMICAL SOCIETY, 1953, (OCT): : 3265 - 3270
123456