Vinyl-diazine triphenylamines and their N-methylated derivatives: Synthesis, photophysical properties and application for staining DNA

被引：42
作者：
Aranda, Ana I. [1 ,2 ]
Achelle, Sylvain [1 ,2 ]
Hammerer, Fabien [1 ,2 ]
Mahuteau-Betzer, Florence [1 ,2 ]
Teulade-Fichou, Marie-Paule [1 ,2 ]
机构：
[1] Univ Paris 11, Ctr Univ Orsay, CNRS, UMR 176,Inst Curie, F-91405 Orsay, France
[2] Univ Paris 11, Ctr Univ Orsay, Sect Rech, Inst Curie, F-91405 Orsay, France
来源：
DYES AND PIGMENTS | 2012年 / 95卷 / 02期
关键词：
Diazines; Pyrimidine; Pyrazine; Triphenylamine; Fluorescence; DNA strainers; LIGHT-EMITTING PROPERTIES; 2-PHOTON ABSORPTION; FLUORESCENT PROPERTIES; OPTICAL-PROPERTIES; FACILE SYNTHESIS; PYRIMIDINE-CORE; BUILDING-BLOCK; RED EMITTERS; CHROMOPHORES; OLIGOMERS;
D O I：
10.1016/j.dyepig.2012.04.009
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
In this paper we describe the synthesis of vinyl-diazine triphenylamines. These compounds exhibit strong green-yellow fluorescence in dichloromethane solution, important emission solvatochromism and acidochromism. Regioselective N-alkylation of these dyes provides cationic compounds that exhibit affinity for double-stranded DNA. Binding to the biopolymer results in a strong bathochromic shift and increase of the emission intensity. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码：400 / 407
页数：8
相关论文
共 58 条
  • [1] Star- and banana-shaped oligomers with a pyrimidine core:: Synthesis and light-emitting properties
    Achelle, Sylvain
    Ramondenc, Yvan
    Marsais, Francis
    Ple, Nelly
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (18) : 3129 - 3140
  • [2] Bis- and tris(arylethynyl)pyrimidine oligomers:: synthesis and light-emitting properties
    Achelle, Sylvain
    Ramondenc, Yvan
    Dupas, Georges
    Ple, Nelly
    [J]. TETRAHEDRON, 2008, 64 (12) : 2783 - 2791
  • [3] Pyrimidine Ring as Building Block for the Synthesis of Functionalized II-Conjugated Materials
    Achelle, Sylvain
    Ple, Nelly
    [J]. CURRENT ORGANIC SYNTHESIS, 2012, 9 (02) : 163 - 187
  • [4] Bisporphyrin connected by pyrimidine: synthesis and photophysical properties
    Achelle, Sylvain
    Saettel, Nicolas
    Baldeck, Patrice
    Teulade Fichou, Marie-Paule
    Maillard, Philippe
    [J]. JOURNAL OF PORPHYRINS AND PHTHALOCYANINES, 2010, 14 (10) : 877 - 884
  • [5] V-Shaped 4,6-Bis(arylvinyl)pyrimidine Oligomers: Synthesis and Optical Properties
    Achelle, Sylvain
    Nouira, Ines
    Pfaffinger, Bernd
    Ramondenc, Yvan
    Ple, Nelly
    Rodriguez-Lopez, Julian
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (10) : 3711 - 3717
  • [6] A new class of bipyrimidine-based octupolar chromophores: synthesis, fluorescent and quadratic nonlinear optical properties
    Akdas-Kilig, Huriye
    Roisnel, Thierry
    Ledoux, Isabelle
    Le Bozec, Hubert
    [J]. NEW JOURNAL OF CHEMISTRY, 2009, 33 (07) : 1470 - 1473
  • [7] Vinyl-pyridinium triphenylamines: Novel far-red emitters with high photostability and two-photon absorption properties for staining DNA
    Allain, Clemence
    Schmidt, Falk
    Lartia, Remy
    Bordeau, Guillaume
    Fiorini-Debuisschert, Celine
    Charra, Fabrice
    Tauc, Patrick
    Teulade-Fichou, Marie-Paule
    [J]. CHEMBIOCHEM, 2007, 8 (04) : 424 - 433
  • [8] [Anonymous], 2001, SYNTH COMMUN, DOI DOI 10.1081/SCC-100105893
  • [9] meta-Substituted triphenylamines as new dyes displaying exceptionally large Stokes shifts
    Bordeau, Guillaume
    Lartia, Remy
    Teulade-Fichou, Marie-Paule
    [J]. TETRAHEDRON LETTERS, 2010, 51 (33) : 4429 - 4432
  • [10] Trinaphthylamines as Robust Organic Materials for Two-Photon-Induced Fluorescence
    Bordeau, Guillaume
    Lartia, Remy
    Metge, Germain
    Fiorini-Debuisschert, Celine
    Charra, Fabrice
    Teulade-Fichou, Marie-Paule
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (50) : 16836 - +
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