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 [J].
Achelle, Sylvain ;
Ramondenc, Yvan ;
Marsais, Francis ;
Ple, Nelly .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (18) :3129-3140
[2]   Bis- and tris(arylethynyl)pyrimidine oligomers:: synthesis and light-emitting properties [J].
Achelle, Sylvain ;
Ramondenc, Yvan ;
Dupas, Georges ;
Ple, Nelly .
TETRAHEDRON, 2008, 64 (12) :2783-2791
[3]   Pyrimidine Ring as Building Block for the Synthesis of Functionalized II-Conjugated Materials [J].
Achelle, Sylvain ;
Ple, Nelly .
CURRENT ORGANIC SYNTHESIS, 2012, 9 (02) :163-187
[4]   Bisporphyrin connected by pyrimidine: synthesis and photophysical properties [J].
Achelle, Sylvain ;
Saettel, Nicolas ;
Baldeck, Patrice ;
Teulade Fichou, Marie-Paule ;
Maillard, Philippe .
JOURNAL OF PORPHYRINS AND PHTHALOCYANINES, 2010, 14 (10) :877-884
[5]   V-Shaped 4,6-Bis(arylvinyl)pyrimidine Oligomers: Synthesis and Optical Properties [J].
Achelle, Sylvain ;
Nouira, Ines ;
Pfaffinger, Bernd ;
Ramondenc, Yvan ;
Ple, Nelly ;
Rodriguez-Lopez, Julian .
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 [J].
Akdas-Kilig, Huriye ;
Roisnel, Thierry ;
Ledoux, Isabelle ;
Le Bozec, Hubert .
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 [J].
Allain, Clemence ;
Schmidt, Falk ;
Lartia, Remy ;
Bordeau, Guillaume ;
Fiorini-Debuisschert, Celine ;
Charra, Fabrice ;
Tauc, Patrick ;
Teulade-Fichou, Marie-Paule .
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 [J].
Bordeau, Guillaume ;
Lartia, Remy ;
Teulade-Fichou, Marie-Paule .
TETRAHEDRON LETTERS, 2010, 51 (33) :4429-4432
[10]   Trinaphthylamines as Robust Organic Materials for Two-Photon-Induced Fluorescence [J].
Bordeau, Guillaume ;
Lartia, Remy ;
Metge, Germain ;
Fiorini-Debuisschert, Celine ;
Charra, Fabrice ;
Teulade-Fichou, Marie-Paule .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (50) :16836-+
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