Synthesis and characterization of new fluorinated tetrazines displaying a high fluorescence yield

被引：7

作者：

Ben Chaabane, Radhia ^{[1
]}

Guermazi, Refka ^{[1
]}

Clavier, Gilles ^{[2
]}

Audebert, Pierre ^{[2
]}

Hedhli, Ahmed ^{[1
]}

机构：

[1] Ecole Super Sci & Tech Tunis, Lab Chim Mol Organ, Tunis 1089, Tunisia

[2] UniverSud, CNRS, ENS Cachan, PPSM, F-94230 Cachan, France

来源：

DYES AND PIGMENTS | 2014年 / 108卷

关键词：

Tetrazine; Nitrogen; Fluorine; Fluorescence; Perfluorinated chains; Electrochemistry; MEDICINAL CHEMISTRY; S-TETRAZINES; ANTITUMOR-ACTIVITY; ELECTRONIC STATES; HETEROATOMS; DERIVATIVES; MOLECULES;

D O I：

10.1016/j.dyepig.2014.03.031

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

New tetrazines substituted with perfluorinated alkyl chains have been synthesized and their electrochemical and photophysical properties investigated under various conditions. Their fluorescence quantum yields in dichloromethane appear to be interestingly slightly higher than with classical tetrazines, placing these new derivatives among the most fluorescent tetrazines characterized to date. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：64 / 69

页数：6

共 26 条

[1]

[Anonymous], 2000, HDB HETEROCYCLIC CHE

[2] Synthesis and properties of new tetrazines substituted by heteroatoms:: Towards the world's smallest organic fluorophores [J].

Audebert, P ;

Miomandre, F ;

Clavier, G ;

Vernières, MC ;

Badré, S ;

Méallet-Renault, R .

CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (19) :5667-5673

[3] Fluorine in medicinal chemistry [J].

Böhm, HJ ;

Banner, D ;

Bendels, S ;

Kansy, M ;

Kuhn, B ;

Müller, K ;

Obst-Sander, U ;

Stahl, M .

CHEMBIOCHEM, 2004, 5 (05) :637-643

[4] s-Tetrazines as Building Blocks for New Functional Molecules and Molecular Materials [J].

Clavier, Gilles ;

Audebert, Pierre .

CHEMICAL REVIEWS, 2010, 110 (06) :3299-3314

[5] SPIN-ORBIT COUPLING AND RADIATIONLESS PROCESSES IN NITROGEN HETEROCYCLICS [J].

ELSAYED, MA .

JOURNAL OF CHEMICAL PHYSICS, 1963, 38 (12) :2834-&

[6]

Frisch JM, 2004, GAUSSIAN 03 REVISION

[7] PE SPECTRA OF DISUBSTITUTED 1,2,4,5-TETRAZINES [J].

GLEITER, R ;

SCHEHLMANN, V ;

LARSEN, JS ;

FISCHER, H ;

NEUGEBAUER, FA .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (24) :5756-5762

[8] New tetrazines substituted by heteroatoms including the first tetrazine based cyclophane:: Synthesis and electrochemical properties [J].

Gong, Yong-Hua ;

Audebert, Pierre ;

Tang, Jie ;

Miomandre, Fabien ;

Clavier, Gilles ;

Badre, Sophie ;

Meallet-Renault, Rachel ;

Marrot, Jerome .

JOURNAL OF ELECTROANALYTICAL CHEMISTRY, 2006, 592 (02) :147-152

[9] Synthesis and Physical Chemistry of s-Tetrazines: Which Ones are Fluorescent and Why? [J].

Gong, Yong-Hua ;

Miomandre, Fabien ;

Meallet-Renault, Rachel ;

Badre, Sophie ;

Galmiche, Laurent ;

Tang, Jie ;

Audebert, Pierre ;

Clavier, Gilles .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (35) :6121-6128

[10] Synthesis and antitumor activity of s-tetrazine derivatives [J].

Hu, WX ;

Rao, GW ;

Sun, YQ .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (05) :1177-1181

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