Planar β-linked oligothiophenes based on thieno[3,2-b]thiophene and dithieno[3,2-b:2′,3′-d]thiophene fused units

被引：29
|
作者：
San Miguel, Lidaris
Porter, William W., III
Matzger, Adam J.
机构：
[1] Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA
[2] Univ Michigan, Macromol Sci & Engn Program, Ann Arbor, MI 48109 USA
来源：
ORGANIC LETTERS | 2007年 / 9卷 / 06期
关键词：
D O I：
10.1021/ol0630393
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A series of planar beta-linked oligothiophenes based on thieno [3,2-b]thiophene and dithieno[3,2-b:'2,3'-d]thiophene fused units were synthesized. The optical data indicate a blue shift of the absorption maximum in comparison to the alpha-linked analogues due to cross-conjugation between fused rings. The crystal structures of 3,3'-bi(thieno[3,2-b]thiophene) and 3,3'; 6', 3"-ter(thieno-[3,2-b]thiophene) reveal edge-to-face pi-stacked dimer motifs, whereas the crystal structure of 3,3'-bis(dithieno[3,2- b:2',3'-d] thiophene) consists of face-to-face pi-stacked molecules.
引用
收藏
页码：1005 / 1008
页数：4
相关论文
共 50 条
  • [1] Planar β-linked oligothiophenes based on thieno[3,2-b]thiophene and dithieno[3,2-b,2′,3′-d]thiophene fused units
    San Miguel, Lidaris
    Matzger, Adam J.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 233
  • [2] SYNTHESIS OF DITHIENO[3,2-b:2 ',3 '-d]THIOPHENE
    Frey, Joseph
    Proemmel, Steffen
    Armitage, Michael A.
    Holmes, Andrew B.
    ORGANIC SYNTHESES, 2006, 83 : 209 - +
  • [3] AN EFFICIENT SYNTHESIS OF QUINONE DERIVATIVES OF THIENO[3,2-B]THIOPHENE AND THIENO[3,2-B]THIENO[2',3'-D]THIOPHENE AND THEIR SPECTRAL PROPERTIES
    MAZAKI, Y
    TAKIGUCHI, N
    KOBAYASHI, K
    CHEMISTRY LETTERS, 1991, (07) : 1117 - 1120
  • [4] Novel ferroelectric liquid crystals based on fused thieno[3,2-b]furan and thieno[3,2-b]thiophene cores
    Cernovska, Katerina
    Kosata, Bedrich
    Svoboda, Jiri
    Novotna, Vladimira
    Glogarova, Milada
    LIQUID CRYSTALS, 2006, 33 (09) : 987 - 996
  • [5] Efficient Methods for the Synthesis of Thieno[3,2-b]thiophene and Thieno[3,2-b]furan Derivatives
    Shirinian, Valerii Z.
    Shimkin, Alexey A.
    Tipikin, Stepan N.
    Krayushkin, Mikhail M.
    SYNTHESIS-STUTTGART, 2009, (22): : 3803 - 3806
  • [6] Facile and Scalable Synthesis of the Fused-Ring Heterocycles Thieno[3,2-b]-thiophene and Thieno[3,2-b]furan
    Henssler, John T.
    Matzger, Adam J.
    ORGANIC LETTERS, 2009, 11 (14) : 3144 - 3147
  • [7] Novel soluble thieno[3,2-b] thiophene fused porphyrazine
    Casey, Abby
    Han, Yang
    Wyatt, Mark F.
    Anthopoulos, Thomas D.
    Heeney, Martin
    RSC Advances, 2015, 5 (110): : 90645 - 90650
  • [8] A convenient and improved synthesis of dithieno[3,2-b:2′,3′-d]thiophene
    Allared, F
    Hellberg, J
    Remonen, T
    TETRAHEDRON LETTERS, 2002, 43 (08) : 1553 - 1554
  • [9] Photochromism of diarylethenes containing dithieno[3,2-b:2′,3′-d]thiophene
    Wang, Hongke
    Xu, Wei
    Zhu, Daoben
    DYES AND PIGMENTS, 2013, 97 (02) : 303 - 310
  • [10] Synthesis and characterization of 3-(4-fluorophenyl)thieno[3,2-b]thiophene and 3,3′-(4-fluorophenyl)dithieno[3,2-b;2′,3′-d]thiophene molecules
    Topal, Sema
    Topal, Sebahat
    Ulukan, Pelin
    Ustamehmetoglu, Belkis
    Ozturk, Turan
    Sezer, Esma
    ELECTROCHIMICA ACTA, 2021, 390
12345