BODIPY-bridged push-pull chromophores: optical and electrochemical properties

被引：45
作者：
Niu, Songlin [1 ]
Ulrich, Gilles [1 ]
Retailleau, Pascal [2 ]
Ziessel, Raymond [1 ]
机构：
[1] ECPM, LCOSA, UMR7515, F-67087 Strasbourg 02, France
[2] ICSN CNRS, Lab Cristallochim, F-91198 Gif Sur Yvette, France
来源：
TETRAHEDRON LETTERS | 2011年 / 52卷 / 38期
关键词：
BODIPY; Push-pull; Cycloaddition; Tetracyano; Fluorescence; Electrochemistry; INTRAMOLECULAR CHARGE-TRANSFER; DYES; FLUORESCENCE; DERIVATIVES; CYCLOADDITION; CHEMISTRY; DESIGN;
D O I：
10.1016/j.tetlet.2011.07.028
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A series of BODIPY bridged push-pull chromophores were prepared by a sequence of reactions involving: i) cross-coupling reactions promoted by palladium complexes; ii) Knoevenagel condensation leading to dicyano derivatives; iii) [2+2] cycloaddition. The last reaction is regioselective, providing mono-derivatives with anisole substituents. With dimethylaminophenyl donor groups, double addition is feasible, providing highly colored dyes displaying remarkable electrochemical properties. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码：4848 / 4853
页数：6
相关论文
共 50 条
  • [21] 4-substituted push-pull quinazoline chromophores with extended π-conjugated linker
    Bonnaud, Thibault
    Scaviner, Mathieu
    Robin-le Guen, Francoise
    Achelle, Sylvain
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2024, 61 (02) : 358 - 364
  • [22] Nonplanar Push-Pull Chromophores for Opto-Electronic Applications
    Breiten, Benjamin
    Biaggio, Ivan
    Diederich, Francois
    CHIMIA, 2010, 64 (06) : 409 - 413
  • [23] Charge-Recombination Fluorescence from Push-Pull Electronic Systems Constructed around Amino-Substituted Styryl-BODIPY Dyes
    Nano, Adela
    Ziessel, Raymond
    Stachelek, Patrycya
    Harriman, Anthony
    CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (40) : 13528 - 13537
  • [24] New 8-substituted BODIPY-based chromophores: synthesis, optical and electrochemical properties
    Vologdin, Nikolay
    Achelle, Sylvain
    Gauthier, Sebastien
    Caro, Bertrand
    Guen, Francoise Robin-le
    HETEROCYCLIC COMMUNICATIONS, 2016, 22 (06) : 339 - 345
  • [25] Push-pull biphenyl and tolane derivatives as novel luminescent liquid crystals: synthesis and properties
    Iida, Yuuto
    Shimomura, Yoshimichi
    Tokita, Masatoshi
    Konishi, Gen-ichi
    LIQUID CRYSTALS, 2024, : 2032 - 2045
  • [26] Polyaromatic hydrocarbon antennas as tools for tuning properties of push-pull difluoroborates
    Glodek, Marta
    Petrusevich, Elizaveta F.
    Plazuk, Damian
    Jacquemin, Denis
    Osmialowski, Borys
    DYES AND PIGMENTS, 2023, 212
  • [27] Acetylene-Derived Strong Organic Acceptors for Planar and Nonplanar Push-Pull Chromophores
    Kivala, Milan
    Diederich, Francois
    ACCOUNTS OF CHEMICAL RESEARCH, 2009, 42 (02) : 235 - 248
  • [28] Synthesis and optical properties of push-pull type tetrapyrazinoporphyrazines
    Lee, BH
    Jaung, JY
    Jang, SC
    Yi, SC
    DYES AND PIGMENTS, 2005, 65 (02) : 159 - 167
  • [29] Push-Pull Azo-Chromophores Containing Two Fused Pentatomic Heterocycles and Their Nonlinear Optical Properties
    Centore, Roberto
    Fusco, Sandra
    Peluso, Andrea
    Capobianco, Amedeo
    Stolte, Matthias
    Archetti, Graziano
    Kuball, Hans-Georg
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (21) : 3535 - 3543
  • [30] The effects of molecular aggregation and isomerization on the fluorescence of "push-pull" hyperpolarizable chromophores
    Smith, GJ
    Dunford, CL
    Kay, AJ
    Woolhouse, AD
    JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 2006, 179 (03) : 237 - 242
12345