A versatile scaffold for facile synthesis of fluorescent cyano-substituted stilbenes

被引:10
作者
Hayashi, Shotaro [1 ]
Sakamoto, Minami [2 ]
Ishiwari, Fumitaka [2 ]
Fukushima, Takanori [2 ]
Yamamoto, Shin-ichi [1 ]
Koizumi, Toshio [1 ]
机构
[1] Natl Def Acad, Dept Appl Chem, 1-10-20 Hashirimizu, Yokosuka, Kanagawa 2398686, Japan
[2] Tokyo Inst Technol, Inst Innovat Res, Lab Chem & Life Sci, Midori Ku, 4259 Nagatsuta, Yokohama, Kanagawa 2268503, Japan
基金
日本学术振兴会;
关键词
pi-Conjugated molecule; Fluorescence; Scaffold; WITTIG OLEFINATION REACTION; CONJUGATED POLYMER-FILMS; CROSS-COUPLING REACTIONS; CARBON BOND FORMATION; ENHANCED EMISSION; PALLADIUM; DERIVATIVES; ARYLATION; CATALYSIS; CRYSTALS;
D O I
10.1016/j.tet.2019.01.012
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Here we report the facile derivatization of a cyano-substituted stilbene into higher pi-extended analogues. The cyano-substituted stilbene, which serves as a synthetic scaffold, has a bromo group and a formyl group on its 4- and 4'-position of the phenylene rings and thus readily undergoes selective transformation into other functional groups using various simple organic reactions. The resultant pi-conjugated molecules that contain a cyano-substituted stilbene skeleton exhibit fluorescence in solution and in the solid state. (C) 2019 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1079 / 1084
页数:6
相关论文
共 63 条
  • [1] Enhanced emission and its switching in fluorescent organic nanoparticles
    An, BK
    Kwon, SK
    Jung, SD
    Park, SY
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (48) : 14410 - 14415
  • [2] π-Conjugated Cyanostilbene Derivatives: A Unique Self-Assembly Motif for Molecular Nanostructures with Enhanced Emission and Transport
    An, Byeong-Kwan
    Gierschner, Johannes
    Park, Soo Young
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2012, 45 (04) : 544 - 554
  • [3] [Anonymous], ANGEW CHEM INT ED EN
  • [4] Diversity-Oriented Synthesis of Polycyclic Scaffolds by Modification of an Anodic Product Derived from 2,4-Dimethylphenol
    Barjau, Joaquin
    Schnakenburg, Gregor
    Waldvogel, Siegfried R.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (06) : 1415 - 1419
  • [5] CYCLOALKENES BY INTRAMOLECULAR WITTIG REACTION
    BECKER, KB
    [J]. TETRAHEDRON, 1980, 36 (12) : 1717 - 1745
  • [6] Controlled/living radical polymerization: Features, developments, and perspectives
    Braunecker, Wade A.
    Matyjaszewski, Krzysztof
    [J]. PROGRESS IN POLYMER SCIENCE, 2007, 32 (01) : 93 - 146
  • [7] Recent advances in organic mechanofluorochromic materials
    Chi, Zhenguo
    Zhang, Xiqi
    Xu, Bingjia
    Zhou, Xie
    Ma, Chunping
    Zhang, Yi
    Liu, Siwei
    Xu, Jiarui
    [J]. CHEMICAL SOCIETY REVIEWS, 2012, 41 (10) : 3878 - 3896
  • [8] Chain-growth control in free radical polymerization
    Colombani, D
    [J]. PROGRESS IN POLYMER SCIENCE, 1997, 22 (08) : 1649 - 1720
  • [9] Effect of AIE Substituents on the Fluorescence of Tetraphenylethene-Containing BODIPY Derivatives
    Gomez-Duran, Cesar F. Azael
    Hu, Rongrong
    Feng, Guangxue
    Li, Tingzhong
    Bu, Fan
    Arseneault, Mathieu
    Liu, Bin
    Pena-Cabrera, Eduardo
    Tang, Ben Zhong
    [J]. ACS APPLIED MATERIALS & INTERFACES, 2015, 7 (28) : 15168 - 15176
  • [10] Creating Elastic Organic Crystals of π-Conjugated Molecules with Bending Mechanofluorochromism and Flexible Optical Waveguide
    Hayashi, Shotaro
    Yamamoto, Shun-ya
    Takeuchi, Daisuke
    Ie, Yutaka
    Takagi, Koji
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (52) : 17002 - 17008