The geometry and absorption of diketo-pyrrolo-pyrroles substituted with various aryls

Dyes and Pigments

Volumn 85, Issue 1-2, 2010, Pages 27-36

  Luňák Jr , Stanislav ^a   Havel, Lukáš ^a   Vyňuchal, Jan ^b,c   Horáková, Petra ^a   Kučerík, Jiří ^d   Weiter, Martin ^d   Hrdina, Radim ^a  

^a UNIVERSITY OF PARDUBICE   (Czech Republic)

^b Vyzkumny ustav organickych syntez as   (Czech Republic)

^c SYNTHESIA A S   (Czech Republic)

^d BRNO UNIVERSITY OF TECHNOLOGY   (Czech Republic)

Author keywords

Absorption; Diketo pyrrolo pyrroles (DPP); Fluorescence; Time dependent density functional theory (TD DFT)

Indexed keywords

BATHOCHROMIC SHIFT; DIHEDRAL ANGLES; EXPERIMENTAL DATA; FLUORESCENCE EXCITATION; HYPERCHROMIC SHIFT; LOW TEMPERATURES; OUT-OF-PLANE; SUB-BANDS; THEORETICAL CALCULATIONS; TIME DEPENDENT DENSITY FUNCTIONAL THEORY; UNSYMMETRICAL; VIBRATIONAL STRUCTURES; VIBRONIC BANDS;

ABSORPTION; FLUORESCENCE; OPTICAL FILTERS; ORGANIC POLYMERS; ORGANIC SOLVENTS; POTASSIUM COMPOUNDS; PROBABILITY DENSITY FUNCTION; STEEL BEAMS AND GIRDERS;

DENSITY FUNCTIONAL THEORY;

ABSORPTION; CHEMICAL COMPOUND; FLUORESCENCE; ORGANIC COMPOUND; QUALITATIVE ANALYSIS; SOLVENT; SYNTHESIS;

EID: 70449705825     PISSN: 01437208     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dyepig.2009.09.014     Document Type: Article

References (22)

1. Luňák Jr. S., Vyňuchal J., Vala M., Havel L., and Hrdina R. The syntheses, absorption and fluorescence of polar diketo-pyrrolo-pyrroles. Dyes Pigments 82 (2009) 102-108
2. Iqbal A, Cassar L. EP 98808 (Ciba-Geigy, 1982).
3. Herbst M., and Hunger K. Industrial organic pigments (1993), VCH, Weinheim
4. Mizuguchi J., and Rihs G. Electronic-spectra of 1,4-diketo-3,6-diphenyl-pyrrolo-[3,4-c]-pyrrole in the solid-state. Ber Bunsenges Phys Chem 96 4 (1992) 597-606
5. 2. Z Krystallogr - New Cryst Struct 217 (2002) 43-44
6. Morton C.J.H., Gilmour R., Smith D.M., Lightfoot P., Slawin A.M.Z., and MacLean E.J. Synthetic studies related to diketopyrrolopyrrole (DPP) pigments. Part 1: the search for alkenyl DPPs. Unsaturated nitriles in standard DPP syntheses: a novel cyclopenta[c]pyrrolone chromophore. Tetrahedron 58 (2002) 5547-5565
7. Iqbal A., Kirchmayr R., Pfenninger J., Rochat A.C., and Wallquist O. The synthesis and properties of 1,4-diketo-pyrrolo[3,4-c]pyrroles. Bull Soc Chimi Belges 97 8-9 (1988) 615-643
8. Adachi A., and Nakamura S. Absorption spectrum shift in the solid state. A MO study of pyrrolopyrrole pigment. J Phys Chem 98 (1994) 1796-1801
9. Wallquist O. In: Smith H.M. (Ed). High performance pigments (2002), Wiley-VCH, Weinheim 159-184
10. Vala M., Weiter M., Vyňuchal J., Toman P., and Luňák Jr. S. Comparative studies of diphenyl-diketo-pyrrolopyrrole derivatives for electroluminescence applications. J Fluoresc 18 6 (2008) 1181-1186
11. Vyňuchal J., Luňák Jr. S., Hatlapatková A., Hrdina R., Lyčka A., Havel L., et al. The synthesis, absorption, fluorescence and photoisomerisation of 2-aryl-4-arylmethylidene-pyrroline-5-ones. Dyes Pigments 77 2 (2008) 266-276
12. Wang L., Li H., and Li P. Task-specific ionic liquid as base, ligand and reaction medium for the palladium-catalyzed Heck reaction. Tetrahedron 65 1 (2009) 364-368
13. Becke A.D. Density-functional thermochemistry. III. The role of exact exchange. J Chem Phys 98 (1993) 5648-5652
14. Jacquemin D., Perpète E.A., Ciofini I., and Adamo C. Accurate simulation of optical properties in dyes. Acc Chem Res 42 (2009) 326-334
15. Tomasi J., Mennucci B., and Cammi R. Quantum mechanical continuum solvation models. Chem Rev 105 (2005) 2999-3094
16. Gaussian 03 W., Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Montgomery Jr. J.A., Vreven T., Kudin K.N., Burant J.C., Millam J.M., Iyengar S.S., Tomasi J., Barone V., Mennucci B., Cossi M., Scalmani G., Rega N., Petersson G.A., Nakatsuji H., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Klene M., Li X., Knox J.E., Hratchian H.P., Cross J.B., Bakken V., Adamo C., Jaramillo J., Gomperts R., Stratmann R.E., Yazyev O., Austin A.J., Cammi R., Pomelli C., Ochterski J.W., Ayala P.Y., Morokuma K., Voth G.A., Salvador P., Dannenberg J.J., Zakrzewski V.G., Dapprich S., Daniels A.D., Strain M.C., Farkas O., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Ortiz J.V., Cui Q., Baboul A.G., Clifford S., Cioslowski J., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Challacombe M., Gill P.M.W., Johnson B., Chen W., Wong M.W., Gonzalez C., and Pople J.A. (2004), Gaussian, Inc., Wallingford, CT
17. Zoon P.D., and Brouwer A.M. A push-pull aromatic chromophore with a touch of merocyanine. Photochem Photobiol Sci 8 (2009) 345-353
18. Castel N, Fischer E, Bartocci G, Masetti F, Mazzucato U. Viscosity-induced emission anomalies in 1,2-diarylethylenes and distyryl-benzenes and -naphthalenes. J Chem Soc Perkin Trans II 1985, 1969-1975.
19. 12. Acta Crystallogr C 40 (1984) 428-431
20. Watanabe H., Okamoto Y., Furuya K., Sakamoto A., and Tasumi M. Vibrational analysis of trans-stilbenes in the ground and excited singlet electronic states revisited. J Phys Chem A 106 (2002) 3318-3324
21. Catalán J. On the nonplanarity of trans-stilbene. Chem Phys Lett 421 (2006) 134-137
22. Dreuw A., and Head-Gordon M. Single-reference ab initio methods for the calculation of excited states of large molecules. Chem Rev 102 11 (2005) 4009-4037