Absorption and fluorescence of soluble polar diketo-pyrrolo-pyrroles

Dyes and Pigments

Volumn 91, Issue 3, 2011, Pages 269-278

  Luňák Jr , Stanislav ^a   Vala, Martin ^b   Vyňuchal, Jan ^a,c,d   Ouzzane, Imad ^b   Horáková, Petra ^a   Možíšková, Petra ^b   Eliáš, Zdeněk ^a   Weiter, Martin ^b  

^a UNIVERSITY OF PARDUBICE   (Czech Republic)

^b BRNO UNIVERSITY OF TECHNOLOGY   (Czech Republic)

^c Vyzkumny ustav organickych syntez as   (Czech Republic)

^d SYNTHESIA A S   (Czech Republic)

Author keywords

Diketo pyrrolo pyrrole; Fluorescence; Organic electronics; Solid state fluorescence; Solvatochromism; Twisted intramolecular charge transfer

Indexed keywords

DIKETOPYRROLOPYRROLES; ORGANIC ELECTRONICS; SOLID-STATE FLUORESCENCE; SOLVATOCHROMISMS; TWISTED INTRA-MOLECULAR CHARGE TRANSFERS;

ABSORPTION; CHARGE TRANSFER; EXCITED STATES; ION EXCHANGE; NITROGEN COMPOUNDS; POLYCRYSTALS; POTASSIUM COMPOUNDS; QUANTUM THEORY; QUANTUM YIELD;

FLUORESCENCE;

EID: 79958862840     PISSN: 01437208     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dyepig.2011.05.004     Document Type: Article

References (43)

1. A. Iqbal, M. Jost, R. Kirchmayer, J. Pfenninger, A.C. Rochat, and O. Wallquist Synthesis and properties of 1,4-diketopyrrolo[3,4-c]pyrroles Bulletin des Societes Chimiques Belges 97 8-9 1988 615 643
2. O. Wallquist Diketopyrrolopyrrole (DPP) pigments H.M. Smith, High performance pigments 2002 Wiley-VCH Weinheim 159 184
3. M. Herbst, and K. Hunger Industrial organic pigments 2004 Wiley-VCH Weinheim pp. 487-494
4. R.B. Aïch, Y. Zou, M. Leclerc, and Y. Tao Solvent effect and device optimization of diketopyrrolopyrrole and carbazole copolymer based solar cells Org Electron 11 6 2010 1053 1058
5. L. Bürgi, M. Turbiez, R. Pfeiffer, F. Bienewald, H.J. Kirner, and C. Winnewisser High-mobility ambipolar near-infrared light-emitting polymer field-effect transistors Adv Mater 20 11 2008 2217 2224
6. J.C. Bijleveld, A.P. Zoombelt, S.G.J. Mathijssen, M.M. Wienk, M. Turbiez, and D.M. De Leeuw Poly(diketopyrrolopyrroleterthiophene) for ambipolar logic and photovoltaics J Am Chem Soc 131 46 2009 16616 16617
7. B. Walker, A.B. Tamayo, X.D. Dang, P. Zalar, J.H. Seo, and A. Garcia Nanoscale phase separation and high photovoltaic efficiency in solution-processed, small-molecule bulk heterojunction solar cells Adv Funct Mater 19 19 2009 3063 3069
8. S. Qu, W. Wu, J. Hua, C. Kong, Y. Long, and H. Tian New diketopyrrolopyrrole (DPP) dyes for efficient dye-sensitized solar cells J Phys Chem C 114 2 2010 1343 1349
9. A.B. Tamayo, B. Walker, and T.Q. Nguyen A low band gap, solution processable oligothiophene with a diketopyrrolopyrrole core for use in organic solar cells J Phys Chem C 112 30 2008 11545 11551
10. S. Luňák Jr., J. Vyňuchal, M. Vala, L. Havel, and R. Hrdina The synthesis, absorption and fluorescence of polar diketo-pyrrolo- pyroles Dyes Pigm 82 2 2009 102 108
11. M. Vala, M. Weiter, J. Vyňuchal, P. Toman, and S. Luňák Jr. Comparative studies of diphenyl-diketo-pyrrolopyrrole derivatives for electroluminescence applications J Fluoresc 18 6 2008 1181 1186
12. M. Vala, J. Vyňuchal, P. Toman, M. Weiter, and S. Luňák Jr. Novel, soluble diphenyl-diketo-pyrrolopyrroles: experimental and theoretical study Dyes Pigm 84 2 2010 176 182
13. G. Colonna, T. Pilati, F. Rusconi, and G. Zecchi Synthesis and properties of some new N, N′-disubstituted 2,5-dihydro-1,4-dioxo-3,6- diphenylpyrrolo[3,4-c]pyrroles Dyes Pigm 75 1 2007 125 129 (Pubitemid 46555008)
14. D. Thetford, J. Cherryman, A.P. Chorlton, and R. Docherty Theoretical molecular modelling calculations on the solid state structure of some organic pigments Dyes Pigm 63 3 2004 259 276 (Pubitemid 38889321)
15. T. Potrawa, and H. Langhals Fluorescent dyes with large stokes shifts-soluble dihydropyrrolopyrrolediones Chem Ber 120 7 1987 1075 1078
16. G.M. Fischer, A.P. Ehlers, A. Zumbusch, and E. Daltrozzo Near-infrared dyes and fluorophores based on diketopyrrolopyrroles Angew Chem Int Ed 46 4 2007 3750 3753 (Pubitemid 46981266)
17. T. Imoda, and J. Mizuguchi Strikingly different luminescent properties arising from single crystals grown from solution or from the vapor phase in a diketo-pyrrolo-pyrrole analog J Appl Phys 102 7 2007 073529(1) 073529(7)
18. S.Y. Park, Y. Kubota, K. Funabiki, M. Shiro, and M. Matsui Near-infrared solid-state fluorescent naphtooxazine dyes attached with bulky dibutylamino and perfluoroalkenyloxy groups at 6- and 9-positions Tetrahedron Lett 50 10 2009 1131 1135
19. M. Matsui, R. Ikeda, Y. Kubota, and K. Funabiki Red solid-state fluorescent aminoperfluorophenazines Tetrahedron Lett 50 35 2009 5047 5049
20. S.Y. Park, M. Ebihara, Y. Kubota, K. Funabiki, and M. Matsui The relationship between solid-state fluorescence intensity and molecular packing of coumarin dyes Dyes Pigm 82 3 2009 258 267
21. H. Langhals, T. Potrawa, H. Nöth, and G. Linti The influence of packing effects on the solid-state fluorescence of diketopyrrolopyrroles Angew Chem Int Ed 28 4 1989 478 480
22. A.B. Tamayo, M. Tantiwiwat, B. Walker, and T.Q. Nguyen Design, syntheses, and self-assembly of oligothiophene derivatives with a diketopyrrolopyrrole core J Phys Chem C 112 39 2008 15543 15552
23. J. Kuwabara, T. Yamagata, and T. Kanbara Solid-state structure and optical properties of highly fluorescent diketopyrrolopyrrole derivatives synthesized by cross-coupling reaction Tetrahedron 66 21 2010 3736 3741
24. A.T.R. Williams, S.A. Winfield, and J.N. Miller Relative fluorescence quantum yields using a computer-controlled luminescence spectrometer Analyst (Cambridge, United Kingdom) 108 1290 1983 1067 1071
25. K.G. Casey, and E.L. Quitevis Effect of solvent polarity on nonradiative processes in xanthene dyes: rhodamine B in normal alcohols J Phys Chem 92 23 1988 6590 6594
26. D. Magde, R. Wong, and P.G. Seybold Fluorescence quantum yields and their relation to lifetimes of rhodamine 6G and fluorescein in nine solvents: improved absolute standards for quantum yields Photochem Photobiol 75 4 2002 327 334
27. G.A. Reynolds, and K.H. Drexhage New coumarin dyes with rigidized structure for flashlamp-pumped dye lasers Opt Commun 13 1975 222 225
28. Gaussian 09, Revision A.1, Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, et al., 2009.
29. S. Stas, S. Sergeyev, and Y. Geerts Synthesis of diketopyrrolopyrrole (DPP) derivatives compridsing bithiophene moieties Tetrahedron 66 10 2010 1837 1845
30. Y. Qu, J. Hua, and H. Tian Colorimetric and ratiometric red fluorescent chemosensor for fluoride ion based on diketopyrrolopyrrole Org Lett 12 15 2010 3320 3323
31. S. Luňák Jr., J. Vyňuchal, and R. Hrdina Geometry and absorption of diketo-pyrrolo-pyrrole isomers and their π-isoelectronic furo-furanone analogues J Mol Struct 919 1-3 2009 239 245
32. J. Mizuguchi, A. Grubenmann, G. Wooden, and G. Rihs Structures of 3,6-diphenylpyrrolo[3,4-c]pyrrole-1,4-dione and 2,5-dimethyl-3,6- diphenylpyrrolo[3,4-c]pyrrole-1,4-dione Acta Crystallogr B 48 5 1992 696 700 (The value in the text was taken from file KUHKUT in CSD)
33. I.J. Bruno, J.C. Cole, P.R. Edgington, M. Kessler, C.F. Macrae, and P. McCabe New software for searching the Cambridge Structural Database and visualizing crystal structures Acta Crystallogr B 58 3-1 2002 389 397 (Pubitemid 135702675)
34. File KAKMAL cited in CSD as: Poppe M, Gompper R, Polborn K. 2005, Private Communication.
35. Files XATKIN, NAWREJ, XATKEJ and XATJAE cited in CSD as: Ostermann D, Gompper R, Polborn K. 2005, Private Communication.
36. W. Qin, T. Rohand, M. Baruah, A. Stefan, M. Van der Auweraer, and W. Dehaen Solvent-dependent photophysical properties of borondipyrromethene dyes in solution Chem Phys Lett 420 4-6 2006 562 568 (Pubitemid 43332888)
37. P.D. Zoon, and A.M. Brouwer A push-pull aromatic chromophore with a touch of merocyanine Photochem Photobiol Sci 8 3 2009 345 353
38. H. El-Gezawy, W. Rettig, and R. Lapouyade Solvatochromic behaviour of donor-acceptor-polyenes: dimethylamino-cyano-diphenylbutadiene J Phys Chem A 110 1 2006 67 75
39. F. Terenziani, A. Painelli, C. Katan, M. Charlot, and M. Blanchard-Desce Charge instability in quadrupolar chromophores: symmetry breaking and solvatochromism J Am Chem Soc 128 49 2006 15742 15755 (Pubitemid 44894115)
40. E.Q. Guo, P.H. Ren, Y.L. Zhang, H.C. Zhang, and W.J. Yang Diphenylamine end-capped 1,4-diketo-3,6-diphenylpyrrolo[3,4-c]pyrrole (DPP) derivatives with large two-photon absorption cross-sections and strong two-photon excitation red fluorescence Chem Commun 39 2009 5859 5861
41. Z.R. Grabowski, K. Rotkiewicz, and W. Rettig Structural changes accompanying intramolecular electron transfer: focus on twisted intramolecular charge-transfer states and structures Chem. Rev. 103 10 2003 3899 4031
42. Y. Sonoda, M. Goto, S. Tsuzuki, and N. Tamaoki Fluorescence spectroscopic properties and crystal structure of a series of donor-acceptor diphenylpolyenes J Phys Chem A 110 50 2006 13379 13387 (Pubitemid 46196873)
43. J. Plötner, and A. Dreuw Solid state fluorescence of pigment yellow 101 and derivatives: a conserved property of the individual molecules Phys Chem Chem Phys 8 10 2006 1197 1204