Bidirectional iterative synthesis of alternating benzene-furan oligomers towards molecular wires

被引:37
|
作者
Lee, CF
Liu, CY
Song, HC
Luo, SJ
Tseng, JC
Tso, HH
Luh, TY [1 ]
机构
[1] Acad Sinica, Inst Chem, Taipei 115, Taiwan
[2] Natl Taiwan Univ, Dept Chem, Taipei 106, Taiwan
关键词
D O I
10.1039/b207881c
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Reaction of propargylic dithioacetal 2a with BuLi gives the sulfur-substituted allenyllithium 3a which is allowed to react with a dialdehyde to yield the corresponding alternating benzene-furan oligoaryls 6. Functional group transformation converts the ester groups in 6 to dialdehyde 8 which can be used for the synthesis of higher homologues towards molecular wires. A combination of this furan annulation, Heck reaction and Sonogashira coupling leads to a variety of benzene-furan-alkene/alkyne conjugated oligomers of precise length.
引用
收藏
页码:2824 / 2825
页数:2
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    Mai, Yuliang
    Wen, Wu
    [J]. SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 2017, 170 : 157 - 166
  • [2] Sequential electrochemical oxidation of alternating benzene-furan oligomers
    Lin, Cheng-Lan
    Wu, Yi-Lin
    Chen, Chang-Li
    Chou, Chih-Ming
    Luh, Tien-Yau
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (22): : 8531 - 8534
  • [3] Convergent/divergent synthesis and photophysical studies of alternating benzene-furan oligoaryls from substituted propargylic dithioacetals
    Chou, Chih-Ming
    Chen, Wei-Qiang
    Chen, Jia-Hong
    Lin, Cheng-Lan
    Tseng, Jui-Chang
    Lee, Chin-Fa
    Luh, Tien-Yau
    [J]. CHEMISTRY-AN ASIAN JOURNAL, 2006, 1 (1-2) : 46 - 55
  • [4] Facile Synthesis of Alternating Benzene-Pyrrole Oligomers by Cyclization of Propargylic Dithioacetals and Imines and Their Fluorescent Properties
    Huang, Tong-Hui
    Zhu, Xiao-Lei
    Zhang, Ai-Dong
    Tu, Hai-Yang
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (24) : 4588 - 4594
  • [5] ITERATIVE DIVERGENT CONVERGENT APPROACH TO CONJUGATED OLIGOMERS BY A DOUBLING OF MOLECULAR LENGTH AT EACH ITERATION - A RAPID ROUTE TO POTENTIAL MOLECULAR WIRES
    PEARSON, DL
    SCHUMM, JS
    TOUR, JM
    [J]. MACROMOLECULES, 1994, 27 (08) : 2348 - 2350
  • [7] Synthesis, Optical, and Electronic Properties of Soluble Poly-p-phenylene Oligomers as Models for Molecular Wires
    Banerjee, Moloy
    Shukla, Ruchi
    Rathore, Rajendra
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (05) : 1780 - 1786
  • [8] Synthesis, optical, and electronic properties of soluble poly-p-phenylene oligomers as models for molecular wires
    Banerjee, Moloy
    Shukla, Ruchi
    Rathore, Rajendra
    [J]. Journal of the American Chemical Society, 2009, 131 (05): : 1780 - 1786
  • [9] Convergent synthesis of 10 nm aryleneethynylene molecular wires by an iterative regioselective deprotection/sonogashira coupling protocol
    Wang, CS
    Batsanov, AS
    Bryce, MR
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (01): : 108 - 116
  • [10] Synthesis of building blocks for an iterative approach towards oligomers of the Streptococcus pneumoniae type 1 zwitterionic capsular polysaccharide repeating unit
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    Oscarson, Stefan
    [J]. CANADIAN JOURNAL OF CHEMISTRY, 2016, 94 (11) : 940 - 960