Benzodipyrrolenine-based biscyanine dyes: Synthesis, molecular structure and spectroscopic characterization

Dyes and Pigments

Volumn 85, Issue 1-2, 2010, Pages 7-15

  Klochko, Oleksiy P ^a   Fedyunyayeva, Iryna A ^a   Khabuseva, Sania U ^a   Semenova, Olga M ^a   Terpetschnig, Ewald A ^b   Patsenker, Leonid D ^a,b  

^a INSTITUTE FOR SINGLE CRYSTALS   (Ukraine)

^b SETA BioMedicals   (United States)

Author keywords

Benzodipyrrolenine; Biscyanine dyes; Fluorescence; Spectral properties; Synthesis

Indexed keywords

ACIDIC COMPOUNDS; BENZODIPYRROLENINE; BENZOTHIAZOLES; BENZOXAZOLE; BISCYANINE DYES; EMISSION MAXIMA; END-GROUPS; HIGH EXTINCTION COEFFICIENTS; INDOLENINE; LONG WAVELENGTH; LUMINESCENT PROPERTY; NOVEL METHODS; POLYMETHINE SYSTEMS; RED SHIFT; RED-SHIFTED; SPECTRAL PROPERTIES; SPECTROSCOPIC CHARACTERIZATION; SYNTHESIS;

ABSORPTION; ALDEHYDES; DYES; FLUORESCENCE;

SYNTHESIS (CHEMICAL);

ABSORPTION; CONDENSATION; DYE; FLUORESCENCE; LUMINESCENCE; MOLECULAR STRUCTURE; SYNTHESIS;

EID: 70449518185     PISSN: 01437208     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dyepig.2009.09.007     Document Type: Article

References (38)

1. Hossain M.Z., Ernst L.A., and Nagy J.L. Utility of intensely fluorescent cyanine dyes (CY3) for assay of gap junctional communication by dye-transfer. Neurosci Lett 184 1 (1995) 71-74
2. Lewis J.S., Achilefu S., Garbow J.R., Laforest R., and Welch M.J. Small animal imaging: current technology and perspectives for oncological imaging. Eur J Cancer 38 16 (2002) 2173-2188
3. Weissleder R., and Ntziachristos V. Shedding light onto live molecular targets. Nat Med 9 1 (2003) 123-128
4. Haugland R. Handbook of fluorescent probes and research products. 9th ed. (2002), Mo-lecular Probes, USA
5. Berneth Horst, Bruder Friedrich-Karl. Optical data carrier comprising a cyanine dye as light-absorbent compound in the information layer. US 2005042407 (B2); 2005.
6. Metz Hans-Joachim, Mura Jean-Luc. Lightfast cyanine dye compositions for optical data recording. WO2005023939; 2005.
7. Wurthner F., Wortmann R., Matschiner R., Lukaszuk K., Meerholz K., Denardin Y., et al. Merocyanine dyes in the cyanine limit: a new class of chromophores for photorefractive materials. Angew Chem Int Ed 36 24 (1997) 2765-2768
8. West W., and Gilman P.B. In: James T.J. (Ed). The theory of the photographic process (1977), Macmillian, New York
9. Araki T., Ito E., Oichi K., Mitsumoto R., Sei M., Oji H., et al. NEXAFS Spectroscopic study of organic photographic dyes and their adsorbed states on AgCl and AgBr. J Phys Chem B 101 49 (1997) 10378-10385
10. Sibbett W., and Taylor J.R. Passive mode locking in the near infrared. IEEE J Quantum Electr 20 2 (1984) 108-110
11. Schäfer F.P. Dye lasers. 3rd ed. (1990), Springer-Verlag, Berlin
12. Kiprianov A.I. Absorption spectra of organic dyes containing two chromophores. Russ Chem Rev 40 7 (1971) 594-607
13. Borisevich Yu.E., Kuz'min V.A., and Renge I.V. Effect of π-electron conjugation of the chromophores on the reactivity of the triplet states of dyes with two chromophores in electron-transfer reactions. Russ Chem Bull 30 8 (1981) 1465-1470
14. Ibrayev N.K., Ishchenko A.A., Karamysheva R.K., and Mushkalo I.L. Influence of interaction of chromophores, linked by the unconjugated chain, on the luminescence properties of biscyanine dyes. J Luminescence 90 3 (2000) 81-88
15. Mihailenko F.A., and Boguslavskaya A.N. Cyanine dyes with two conjugated chromophores. X. Ukr Khim Zhurn 35 9 (1969) 943 [in Russian]
16. Kiprianov A.I., Mushkalo I.L., and Mihailenko F.A. Cyanine dyes with two conjugated chromophores. IV. Zh Org Khim 3 11 (1967) 2041-2047 [In Russian]
17. Kiprianov A.I., and Fridman S.G. Cyanine dyes with two conjugated chromophores. VI. Zh Org Khim 4 4 (1968) 696-703 [In Russian]
18. Mihailenko F.A., Boguslavskaya A.N., and Kiprianov A.I. Biscyanines from isomeric benzodipyrrolenines. Chem Heter Comp 7 5 (1971) 578-580
19. Parker C.A. Photoluminescence of solutions (1968), Elsevier, Amsterdam
20. Mujumdar R.B., Ernst L.A., Mujumdar S.R., Lewis C.J., and Waggoner A.S. Cyanine dye labeling reagents: sulfoindocyanine succinimidyl esters. Bioconjug Chem 4 2 (1993) 105-111
21. Stewart J.J.P. Optimization of parameters for semiempirical methods I. Method J Comput Chem 10 2 (1989) 209-220
22. Stewart J.J.P. Optimization of parameters for semiempirical methods II. applications. J Comput Chem 10 2 (1989) 221-232
23. Pariser R., and Parr R.G. A semi-empirical theory of the electronic spectra and electronic structure of complex unsaturated molecules. J Chem Phys 21 3 (1953) 466-471
24. Pople G.A. Electron interaction in unsaturated hydrocarbons. Trans Faraday Soc 49 12 (1953) 1375-1385
25. Fabian J., and Zahradnic R. PPP-Berechnung zum vinylenschift symmetrischer farbstoff. Wiss Z Thechn Univ (Dresden) 26 2 (1977) 315-323
26. Mihailenko F.A., and Boguslavskaya A.N. Synthesis of isomeric benzodipyrrolenines and their derivatives. Chem Heter Comp 7 5 (1971) 574-577
27. Fri H. Über α,β-ungesättigte β-Anilino-carbonyl-Verbindungen als Modellsubstanzen für den Chromophor von C-Curarin-III (C-Fluorocurarin). Chem Ber 92 8 (1959) 1809-1817
28. Patent Application US 2007/0281363 A1.
29. Brooker L.G. Absorption and resonance in dyes. Rev Mod Phys 14 2 (1942) 275-293
30. 1 Interpretation of absorptions of dyes containing heterocyclic nuclei of different basicities. J Am Chem Soc 67 11 (1945) 1875-1889
31. 2. J Am Chem Soc 73 11 (1951) 5332-5350
32. Ishchenko A.A. Structure and spectral-luminescent properties of polymethine dyes. Kiev Naukova Dumka (1994) [in Russian]
33. Richard C.B., and Henry A.K. Absorption and fluorescence properties of cyanine dyes. J Chem Eng Data 22 4 (1977) 69-75
34. Permogorov V.I., Dyadyusha G.G., Mihailenko F.A., and Kiprianov A.I. Electronic spectra of biscyanine dyes. Doklady AN SSSR 188 5 (1969) 1098-1101 [in Russian]
35. Ishchenko A.A., Derevyanko N.A., Kudinova M.A., Dyadyusha G.G., and Tolmachev A.I. Chemical structure and shape of the absorption bands of pyrylocyanine dyes. Theoret Exper Chem 13 6 (1978) 628-631
36. Ishchenko A.A., Zubarovskii V.M., Gromova G.A., and Derevyanko N.A. Influence of polymetine chain length on absorption spectra of unsymmetric cyanine dyes. Zh Org Khim 23 3 (1987) 628-630 [in Russian]
37. Kiprianov A.I. Colour and structure of organic dyes. Ukr Khim Zhurn 33 11 (1967) 1169 [in Russian]
38. Ishchenko A.A., Derevyanko N.A., and Svidro V.A. Constitution and fluorescence spectra of an-symmetryc polymethine dye. Dyes Pigments 19 3 (1992) 169-177