Facile synthesis, structure, and properties of benzo[1,2-b:4,5-b′]dichalcogenophenes

被引：139
|
作者：
Takimiya, K [1 ]
Konda, Y [1 ]
Ebata, H [1 ]
Niihara, N [1 ]
Otsubo, T [1 ]
机构：
[1] Hiroshima Univ, Grad Sch Engn, Dept Appl Chem, Higashihiroshima 7398527, Japan
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 25期
关键词：
D O I：
10.1021/jo051812m
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A general and convenient synthesis of benzo[1,2-b:4,5-b']-dichalcogenophenes including the thiophene (BDT, 1), selenophene (BDS, 2), and tellurophene (BDTe, 3) homologues is developed. Thus synthesized heterocycles are structurally characterized by single-crystal X-ray analysis, and all three homologues are isostructural with one another. They all have completely planar molecular structures packed in a herringbone arrangement. Their physicochemical properties were also elucidated by means of cyclic voltammetry (CV) and LTV-vis spectra.
引用
收藏
页码：10569 / 10571
页数：3
相关论文
共 50 条
  • [21] Design and synthesis of novel heterocyclic building blocks based on benzo[1,2-b:4,5-b′]chalcogenophenes
    Brown, Amy
    Jeffries-El, Malika
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2018, 256
  • [22] Research Progress of Benzo[1,2-b:4,5-b′]difuran Organic Photovoltaic Materials
    Pan, Xuexue
    Huo, Lijun
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2016, 36 (04) : 687 - 699
  • [23] meso-Substituted Porphyrin with Benzo[1,2-b:4,5-b′]dithiophene Moieties
    Urbani, Maxence
    Torres, Tomas
    MACROHETEROCYCLES, 2014, 7 (02): : 133 - 138
  • [24] Metal-free polymerization: synthesis and properties of fused benzo[1,2-b:4,5-b′]bis[b]benzothiophene (BBBT) polymers
    Yao, Liping
    Liao, Hailiang
    Ravva, Mahesh Kumar
    Guo, Yanjun
    Duan, Jiayao
    Wang, Yazhou
    Yu, Yaping
    Li, Zhengke
    McCulloch, Iain
    Yue, Wan
    POLYMER CHEMISTRY, 2020, 11 (22) : 3695 - 3700
  • [25] Selenium-Substituted β-Methylthiobenzo[1,2-b:4,5-b′]dithiophenes: Synthesis, Packing Structure, and Transport Properties
    Takenaka, Hiroyuki
    Ogaki, Takuya
    Wang, Chengyuan
    Kawabata, Kohsuke
    Takimiya, Kazuo
    CHEMISTRY OF MATERIALS, 2019, 31 (17) : 6696 - 6705
  • [26] Synthesis and Photovoltaic Properties of Copolymers Based on Benzo[1,2-b:4,5-b′]dithiophene and Thiophene with Different Conjugated Side Groups
    Gu, Zhaojie
    Tang, Peng
    Zhao, Bin
    Luo, Hao
    Guo, Xia
    Chen, Huajie
    Yu, Gui
    Liu, Xinping
    Shen, Ping
    Tan, Songting
    MACROMOLECULES, 2012, 45 (05) : 2359 - 2366
  • [27] Synthesis and photovoltaic properties of benzo[1,2-b:4,5-b′]dithiophene derivative-based polymers with deep HOMO levels
    Kim, Heung Gyu
    Jo, Sae Byeok
    Shim, Chiyeoung
    Lee, Jaewon
    Shin, Jisoo
    Cho, Eun Chul
    Ihn, Soo-Ghang
    Choi, Yeong Suk
    Kim, Yungi
    Cho, Kilwon
    JOURNAL OF MATERIALS CHEMISTRY, 2012, 22 (34) : 17709 - 17717
  • [28] Synthesis and photovoltaic properties of copolymers based on benzo[1,2-b:4,5-b′]dithiophene and thiazole with different conjugated side groups
    Liu, Xunshan
    Huang, Yuanshuai
    Cao, Zhencai
    Weng, Chao
    Chen, Huajie
    Tan, Songting
    POLYMER CHEMISTRY, 2013, 4 (17) : 4737 - 4745
  • [29] Thiacycle-fused benzo[1,2-b:4,5-b′]dithiophenes (BDTs): synthesis, packing, molecular orientation and semiconducting properties
    Wang, Chengyuan
    Nakamura, Hiroshi
    Sugino, Hiroyoshi
    Takimiya, Kazuo
    JOURNAL OF MATERIALS CHEMISTRY C, 2018, 6 (14) : 3604 - 3612
  • [30] Correlation of structure and photovoltaic performance of benzo[1,2-b:4,5-b′]dithiophene copolymers alternating with different acceptors
    Yu, Jiangsheng
    Zhao, Baofeng
    Nie, Xuemei
    Zhou, Baojin
    Li, Yang
    Hai, Jiefeng
    Zhu, Enwei
    Bian, Linyi
    Wu, Hongbin
    Tang, Weihua
    NEW JOURNAL OF CHEMISTRY, 2015, 39 (03) : 2248 - 2255
12345