Synthesis, photophysical study and BSA association of water-insoluble squaraine dyes

Journal of Photochemistry and Photobiology A: Chemistry

Volumn 252, Issue , 2013, Pages 77-83

  Pisoni, Diego Dos Santos ^a   De Abreu, Marluza Pereira ^a   Petzhold, Cesar Liberato ^a   Rodembusch, Fabiano Severo ^a   Campo, Leandra Franciscato ^a  

^a FEDERAL UNIVERSITY OF RIO GRANDE DO SUL   (Brazil)

Author keywords

BSA association; Photophysical characterisation; Squaraine dyes

Indexed keywords

EID: 84871376109     PISSN: 10106030     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jphotochem.2012.11.013     Document Type: Article

References (41)

1. S.Y. Park, K. Jun, and S.W. Oh The novel functional chromophores based on squarylium dyes Bulletin of the Korean Chemical Society 26 2005 428 432 (Pubitemid 40477336)
2. K.-Y. Law Organic photoconductive materials: recent trends and developments Chemical Reviews 93 1993 449 486
3. S.H. Kim, J.H. Kim, J.Z. Cui, Y.S. Gal, S.H. Jin, and K. Koh Absorption spectra, aggregation and photofading behaviour of near-infrared absorbing squarylium dyes containing pyrimidine moiety Dyes and Pigments 55 2002 1 7 (Pubitemid 38423063)
4. Y. Hyodo, H. Nakazumi, and S. Yagi Synthesis and light absorption/emission properties of novel squarylium dimers bearing a ferrocene spacer Dyes and Pigments 54 2002 163 171 (Pubitemid 35003334)
5. L. Beverina, and P. Salice Squaraine compounds: tailored design and synthesis towards a variety of material science applications European Journal of Organic Chemistry 7 2010 1207 1225
6. K.Y. Law, and F.C. Bailey Squaraine chemistry. Synthesis, characterization, and optical properties of a class of novel unsymmetrical squaraines: [4-(dimethylamino)phenyl](4′-methoxyphenyl)squaraine and its derivatives Journal of Organic Chemistry 57 1992 3278 3286
7. 2: enhanced efficiency of unsymmetrical versus symmetrical squaraine dyes Journal of Photochemistry and Photobiology A: Chemistry 172 2005 63 71 (Pubitemid 40549554)
8. 2 films by an unsymmetrical squaraine dye Journal of the American Chemical Society 129 2007 10320 10321 (Pubitemid 47330234)
9. E.C.P. Smits, S. Setayesh, T.D. Anthopoulos, M. Buechel, W. Nijssen, R. Coehoorn, P.W.M. Blom, B. de Boer, and D.M. de Leeuw Near-infrared light-emitting ambipolar organic field-effect transistors Advanced Materials 19 2007 734 738 (Pubitemid 46932843)
10. L. Beverina, R. Ruffo, G. Patriarca, F.D. Angelis, D. Roberto, S. Righetto, R. Ugo, and G.A. Pagani Second harmonic generation in nonsymmetrical squaraines: tuning of the directional charge transfer character in highly delocalized dyes Journal of Materials Chemistry 19 2009 8190 8197
11. L.-H. Liu, K. Nakatani, R. Pansu, J.-J. Vachon, P. Tauc, and E. Ishow Fluorescence patterning through photoinduced migration of squaraine- functionalized azo derivatives Advanced Materials 19 2007 433 436 (Pubitemid 46925438)
12. B. Oswald, F. Lehmann, L. Simon, E. Terpetschnig, and O.S. Wolfbeis Red laser-induced fluorescence energy transfer in a immunosystem Analytical Biochemistry 280 2000 272 277 (Pubitemid 30308082)
13. Z. Xiang, E.E. Nesterov, J. Skoch, T. Lin, B.T. Hyman, T.M. Swager, B.J. Bacskai, and S.A. Reeves Detection of myelination using a novel histological probe Journal of Histochemistry and Cytochemistry 53 2005 1511 1516 (Pubitemid 41720690)
14. A.L. Tatarets, I.A. Fedyunyayeva, T.S. Dyubko, Y.A. Povrozin, A.O. Doroshenko, E.A. Terpetschnig, and L.D. Patsenker Synthesis of water-soluble, ring-substituted squaraine dyes and their evaluation as fluorescent probes and labels Analytica Chimica Acta 570 2006 214 223 (Pubitemid 43865947)
15. S. Yagi, S. Murayama, Y. Hyodo, Y. Fujie, M. Hirose, and H. Nakazumi Synthesis and light absorption/emission properties of novel bis-squaraine dyes with extensively conjugated π-electron systems Journal of the Chemical Society, Perkin Transactions 1 1 2002 1417 1419 (Pubitemid 34777442)
16. H. Nakazumi, T. Ohta, H. Etoh, T. Uno, C.L. Colyer, Y. Hyodo, and S. Yagi Near-infrared luminescent bis-squaraine dyes linked by a thiophene or pyrene spacer for noncovalent protein labeling Synthetic Metals 73 2005 33 36 (Pubitemid 41277968)
17. E. Terpetschnig, H. Szmacinski, A. Ozinskas, and J.R. Lakowicz Synthesis of squaraine-N-hydroxysuccinimide esters and their biological application as long-wavelength fluorescent labels Analytical Biochemistry 217 1994 197 204 (Pubitemid 24080751)
18. F. Welder, B. Paul, H. Nakazumi, S. Yagi, and C.L. Colyer Symmetric and asymmetric squarylium dyes as noncovalent protein labels: a study by fluorimetry and capillary electrophoresis Journal of Chromatography B 793 2003 93 105 (Pubitemid 36859916)
19. F. Meadows, N. Narayanan, and G. Patonay Determination of protein-dye association by near infrared fluorescence-detected circular dichroism Talanta 50 2000 1149 1155
20. K.D. Volkova, V.B. Kovalska, M.Y. Losytskyy, L.V. Reis, P.F. Santos, P. Almeida, D.E. Lynch, and S.M. Yarmoluk Aza-substituted squaraines for the fluorescent detection of albumins Dyes and Pigments 90 2011 41 47
21. V.S. Jisha, K.T. Arun, M. Hariharan, and D. Ramaiah Site-selective binding and dual mode recognition of serum albumin by a squaraine dye Journal of the American Chemical Society 128 2006 6024 6025
22. G. Patonay, J. Salon, J. Sowell, and L. Strekowski Noncovalent labeling of biomolecules with red and near-infrared dyes Molecules 9 2004 40 49 (Pubitemid 38982439)
23. N. Nizomov, Z.F. Ismailov, S.N. Nizamova, M.K. Salakhitdinova, A.L. Tatarets, L.D. Patsenker, and G. Khodjayev Spectral-luminescent study of interaction of squaraine dyes with biological substances Journal of Molecular Structure 788 2006 36 42 (Pubitemid 43792361)
24. K. Bayo, M. Bayo-Bangoura, M. Mossoyan-Deneux, D. Lexa, and G.V. Ouedraogo Étude des interactions intramoléculaires dans les bimétallophtalocyanines par électrochimie et par spectroélectrochimie Comptes Rendus Chimie 10 2007 482 488
25. J. Savolainen, D. van der Linden, N. Dijkhuizen, and J.L. Herek Characterizing the functional dynamics of zinc phthalocyanine from femtoseconds to nanoseconds Journal of Photochemistry and Photobiology A: Chemistry 196 2008 99 105
26. S. Rudrawar, A. Kondaskar, and A.K. Chakraborti One-pot synthesis of benzothiazoles from carboxylic acids Synthesis 15 2005 2521 2526
27. D.S. Pisoni, C.L. Petzhold, M.P. de Abreu, F.S. Rodembusch, and L.F. Campo Synthesis, spectroscopic characterization and photophysical study of dicyanomethylene-substituted squaraine dyes Comptes Rendus Chimie 15 2012 454 462
28. B.L. Renard, Y. Aubert, and U. Asseline Fluorinated squaraine as near-IR label with improved properties for the labeling of oligonucleotides Tetrahedron Letters 50 2009 1897 1901
29. V.E. Oliveira, G.S. Carvalho, M.I. Yoshida, C.L. Donnici, N.L. Speziali, R. Diniz, and L.F.C. Oliveira Bis(dicyanomethylene)squarate squaraines in their 1,2- and 1,3-forms: synthesis, crystal structure and spectroscopic study of compounds containing alkali metals and tetrabutylammonium ions Journal of Molecular Structure 936 2009 239 249
30. R. Lartia, and U. Asseline New cyanine-oligonucleotide conjugates: relationships between chemical structures and properties Chemistry: A European Journal 12 2006 2270 2281 (Pubitemid 43344546)
31. A.C. Pardal, S.S. Ramos, P.F. Santos, L.V. Reis, and P. Almeida Synthesis and spectroscopic characterisation of n-alkyl quaternary ammonium salts typical precursors of cyanines Molecules 7 2002 320 330 (Pubitemid 38990340)
32. K.D. Volkova, V.B. Kovalska, A.L. Tatarets, L.D. Patsenker, D.V. Kryvorotenko, and S.M. Yarmoluk Spectroscopic study of squaraines as protein-sensitive fluorescent dyes Dyes and Pigments 72 2007 285 292 (Pubitemid 43842968)
33. T. Inoue, S.S. Pandey, N. Fujikawa, Y. Yamaguchi, and S. Hayase Synthesis and characterization of squaric acid based NIR dyes for their application towards dye-sensitized solar cells Journal of Photochemistry and Photobiology A: Chemistry 213 2010 23 29
34. B. Wang, J. Fan, S. Sun, L. Wang, B. Song, and X. Peng 1-(Carbamoylmethyl)-3H-indolium squaraine dyes: synthesis, spectra, photo-stability and association with BSA Dyes and Pigments 85 2010 43 50
35. J.R. Lakowicz Principles of Fluorescence Spectroscopy third ed. 2006 Springer New York pp. 207-214
36. K.-Y. Law, and C.C. Chen Squaraine chemistry effect of orientation on the aggregation of surfactant squaraines in Langmuir-Blodgett films Journal of Physical Chemistry 93 1989 2533 2538
37. 2 electrodes Journal of Physical Chemistry 98 1994 984 988
38. O.P. Dimitriev, A.P. Dimitriyeva, A.I. Tolmachev, and V.V. Kurdyukov Solvent-induced organization of squaraine dyes in solution capillary layers and adsorbed films Journal of Physical Chemistry B 109 2005 4561 4567 (Pubitemid 40429316)
39. Y. Xu, Z. Li, A. Malkovskiy, S. Sun, and Y. Pang Aggregation control of squaraines and their use as near-infrared fluorescent sensors for protein Journal of Physical Chemistry B 114 2010 8574 8580
40. V.S. Jisha, K.T. Arun, M. Hariharan, and D. Ramaiah Site-selective interactions: squaraine dye-serum albumin complexes with enhanced fluorescence and triplet yields Journal of Physical Chemistry B 114 2010 5912 5919
41. A. Mishra, R.K. Behera, P.K. Behera, B.K. Mishra, and G.B. Behera Cyanines during the 1990: a review Chemical Reviews 100 2000 1973 2011