Design and synthesis of sulfobetainic diketopyrrolopyrrole (DPP) laser dyes

被引：25

作者：

Mula, Soumyaditya ^{[1
]}

Hablot, Delphine ^{[2
]}

Jagtap, Krishna K. ^{[3
,4
]}

Heyer, Elodie ^{[2
]}

Ziessel, Raymond ^{[2
]}

机构：

[1] Bhabha Atom Res Ctr, Div Bioorgan, Bombay 400085, Maharashtra, India

[2] Ecole Europeenne Chim Polymeres & Mat, Lab Chim Mol & Spectroscopies Avancees LGOSA, UMR CNRS 7515, F-67087 Strasbourg 02, France

[3] Bhabha Atom Res Ctr, Div Laser & Plasma Technol, Bombay 400085, Maharashtra, India

[4] Univ Poona, Dept Chem, Pune 411007, Maharashtra, India

来源：

NEW JOURNAL OF CHEMISTRY | 2013年 / 37卷 / 02期

关键词：

FIELD-EFFECT TRANSISTORS; POLYMER SOLAR-CELLS; BODIPY DERIVATIVES; ORGANIC PIGMENTS; FLUORESCENCE; CHROMOPHORES; EFFICIENCY; BANDGAP;

D O I：

10.1039/c2nj40569e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We have devised new diketopyrrolopyrrole dyes soluble in polar solvents. The colors of the dyes have been changed by substituting the 3,6-phenyl residues for thiophene groups. The solubility in polar solvents has been improved by alkylation of a dimethylaminopropyne fragment with a 1,3-sultone giving rise to sulfobetaine moieties. These dyes exhibit strong and broad absorption in the visible range (488 nm for the phenyl-DPP and 578 nm for the thiophene-DPP) and intense fluorescence at, respectively, 554 nm (Phi(F) 0.36) and 609 nm (Phi(F) 0.19). The phenyl-DPP dye exhibits a maximum broad band lasing efficiency of 14.6% and a maximum narrow band lasing efficiency of 9.5% with a wide tunable range (554 nm to 616 nm) on excitation with a second harmonic of a Q-switched Nd:YAG (532 nm) laser in MeOH/H2O. The lasing efficiency remains unaffected for hours. The thiophene-DPP dye does not show any lasing action.

引用

页码：303 / 308

页数：6

共 43 条

[1] Efficient Solar Cells Based on an Easily Accessible Diketopyrrolopyrrole Polymer [J].

Bijleveld, Johan C. ;

Gevaerts, Veronique S. ;

Di Nuzzo, Daniele ;

Turbiez, Mathieu ;

Mathijssen, Simon G. J. ;

de Leeuw, Dago M. ;

Wienk, Martijn M. ;

Janssen, Rene A. J. .

ADVANCED MATERIALS, 2010, 22 (35) :E242-+

[2] Unusually large stokes shifts and fluorescence decay times of the charge transfer fluorescence of electron-donor-acceptor-ion pairs - (Configuration transformation in the excited state) [J].

Brlegleb, G. ;

Trencseni, J. ;

Herre, W. .

CHEMICAL PHYSICS LETTERS, 1969, 3 (03) :146-150

[3] Synthesis and Characterization of Optical and Redox Properties of Bithiophene-Functionalized Diketopyrrolopyrrole Chromophores [J].

Buerckstuemmer, Hannah ;

Weissenstein, Annike ;

Bialas, David ;

Wuerthner, Frank .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (08) :2426-2432

[4] High-mobility ambipolar near-infrared light-emitting polymer field-effect transistors [J].

Buergi, Lukas ;

Turbiez, Mathieu ;

Pfeiffer, Reto ;

Bienewald, Frank ;

Kirner, Hans-Joerg ;

Winnewisser, Carsten .

ADVANCED MATERIALS, 2008, 20 (11) :2217-2224

[5] Water-Soluble Phosphonate-Substituted BODIPY Derivatives with Tunable Emission Channels [J].

Bura, Thomas ;

Ziessel, Raymond .

ORGANIC LETTERS, 2011, 13 (12) :3072-3075

[6] Diketopyrrolopyrrole-containing polyfluorenes: Facile method to tune emission color and improve electron affinity [J].

Cao, Derong ;

Liu, Qilin ;

Zeng, Wenjing ;

Han, Shaohu ;

Peng, Junbiao ;

Liu, Shouping .

MACROMOLECULES, 2006, 39 (24) :8347-8355

[7]

Duarte F. J., 2003, Tunable Laser Optics

[8]

FARNUM DG, 1974, TETRAHEDRON LETT, P2549

[9] Evaluation of new organic pigments as laser-active media for a solid-state dye laser [J].

Fukuda, M ;

Kodama, K ;

Yamamoto, H ;

Mito, K .

DYES AND PIGMENTS, 2004, 63 (02) :115-125

[10] Solid-state laser with newly synthesized pigment [J].

Fukuda, M ;

Kodama, K ;

Yamamoto, H ;

Mito, K .

DYES AND PIGMENTS, 2002, 53 (01) :67-72

← 1 2 3 4 5 →