Absorption and fluorescence of arylmethylidenoxindoles and isoindigo

Dyes and Pigments

Volumn 85, Issue 3, 2010, Pages 171-176

  Luňák Jr , Stanislav ^a   Horáková, Petra ^a   Lyčka, Antonín ^b,c  

^a UNIVERSITY OF PARDUBICE   (Czech Republic)

^b Vyzkumny ustav organickych syntez as   (Czech Republic)

^c UNIVERSITY OF HRADEC KRALOVE   (Czech Republic)

Author keywords

Absorption; Arylmethylidenoxindole; Density functional theory; Fluorescence; Isoindigo

Indexed keywords

ABSORPTION MAXIMA; ARYLMETHYLIDENOXINDOLE; DEACTIVATION CHANNEL; E-ISOMERS; ISOINDIGO; LOW TEMPERATURES; LOW-TEMPERATURE ABSORPTION; ON TIME; SPECTRAL FEATURE; TRANS-STILBENE; VIBRONIC BANDS;

ABSORPTION; ABSORPTION SPECTROSCOPY; ALDEHYDES; CHROMATOGRAPHIC ANALYSIS; COLUMN CHROMATOGRAPHY; ELECTRON TRANSITIONS; FLUORESCENCE; GLASS; ISOMERIZATION; ISOMERS;

DENSITY FUNCTIONAL THEORY;

ABSORPTION; CATALYST; CONDENSATION; FLUORESCENCE; SOLVENT; SYNTHESIS; TEMPERATURE;

EID: 72149086391     PISSN: 01437208     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dyepig.2009.11.001     Document Type: Article

References (22)

1. Venkateswarlu S., Panchagnula G.K., Guraiah M.B., and Subbaraju G.V. Isoaurones: synthesis and stereochemical assignments of geometrical isomers. Tetrahedron 62 (2006) 9855-9860
2. Ruveda E.A., and Gonzalez H.A. Geometric isomerism in benzylidenoxindoles. Spectrochim Acta A 26 (1970) 1275-1277
3. Coda A.C., Invernizzi A.G., Righetti P.P., Tacconi G., and Gatti G. (Z)- and (E)-Arylidene-1,3-dihydroindol-2-ones: configuration, conformation, and infrared carbonyl stretching frequencies. J Chem Soc Perkin Trans (1984) 615-619
4. Milanesio M., Viterbo D., Albini A., Fasani E., Bianchi R., and Barzaghi M. Structural study of the solid-state photoaddition reaction of arylideneoxindoles. J Org Chem 65 (2000) 3416-3425
5. 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 Pigm 77 2 (2008) 266-276
6. Vala M., Weiter M., Vyňuchal J., Toman P., and Luňák Jr. S. Comparative studies of Diphenyl-Diketo-Pyrrolopyrroles for electroluminescent applications. J Fluorescence 18 (2008) 1181-1186
7. Perpète E.A., Preat J., André J.M., and Jaquemin D. An ab initio study of the absorption spectra of indirubin, isoindigo, and related derivatives. J Phys Chem A 110 (2006) 5629-5635
8. Luňák Jr. S., Vyňuchal J., Vala M., Havel L., and Hrdina R. The syntheses, absorption and fluorescence of polar diketo-pyrrolo-pyrroles. Dyes Pigm 82 (2009) 102-108
9. Roschger P. Massenfarben von Kunststoffen, EP 632102 (Bayer AG, 1994).
10. Luňák Jr. S., Frumarová B., and Horáková P. Geometry and Raman spectrum of isoindigo. Chem Phys Lett 477 (2009) 116-121
11. Cho H., Iwashita T., Hamaguchi M., and Oyama Y. Stereochemistry of Knoevenagel condensation products from cyanoacetates and aromatic aldehydes. Chem Pharm Bull 39 (1991) 3341-3342
12. 12. Acta Crystallogr C 40 (1984) 428-431
13. Yuan M.S., Fang Q., Ji L., and Yu W.T. 1,1′-Dibutyl-3,3′-biindolinylidene-2,2′-dione. Acta Crystallogr E 63 (2007) 342
14. Krasovitskii B.M., and Bolotin B.M. Organic luminophors (1984), Khimia, Leningrad
15. Itoh T. Franck-Condon analysis of the absorption and fluorescence spectra of all trans α,ω-diphenylpolyenes with one to seven polyene double bonds. J Chem Phys 123 (2005) 064302 (1-6)
16. Zoon P.D., and Brouwer A.M. A push-pull aromatic chromophore with a touch of merocyanine. Photochem Photobiol Sci 8 (2009) 345-353
17. Plötner J., and Dreuw A. Solid state fluorescence of Pigment Yellow 101 and derivatives: a conserved property of the individual molecules. Phys Chem Chem Phys 8 (2006) 1197-1204
18. Langhals H., Potrawa T., Nöth H., and Linti G. The influence of packing effect on the solid-state fluorescence of diketopyrrolopyrroles. Angew Chem Int Ed 28 (1989) 478-480
19. Imoda T., and Mizuguchi J. 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 (2007) 102 073529 (1-7)
20. Catalán J. On the nonplanarity of trans-stilbene. Chem Phys Lett 421 (2006) 134-137
21. Dähne S., and Leupold D. Coupling principles in organic dyes. Angew Chem Int Ed 5 12 (1966) 984-993
22. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, et al., Gaussian, Inc., Wallingford, CT, 2004.