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Properties of singlet- and triplet-excited states of hemicyanine dyes

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Abstract

The fluorescence emission spectra and fluorescence quantum yields of hemicyanine dyes LDS 698, LDS 722, and LDS 730 were measured in different media. No transient species was detected in the laser flash-photolysis experiments performed with Ar-saturated solutions of the dyes in methanol. However, in the presence of 0.08 M potassium iodide, the absorption of the triplet states was clearly observed. Oxygen consumption measurements in the absence and presence of a chemical trap (furfuryl alcohol) in MeOH: H2O (φ r = 1: 1) solutions of the dyes containing KI confirmed the generation of singlet molecular oxygen.

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References

  • Ashwell, G. J., Tyrrell, W. D., & Whittam, A. J. (2004). Molecular rectification: Self-assembled monolayers in which donor-(π-bridge)-acceptor moieties are centrally located and symmetrically coupled to both gold electrodes. Journal of the American Chemical Society, 126, 7102–7110. DOI: 10.1021/ja049633u.

    Article  CAS  Google Scholar 

  • Cao, X., Tolbert, R. W., McHale, J. L., & Edwards, W. D. (1998). Theoretical study of solvent effects on the intramolecular charge transfer of a hemicyanine dye. The Journal of Physical Chemistry A, 102, 2739–2748. DOI: 10.1021/jp972190e.

    Article  CAS  Google Scholar 

  • Cerdán, L., Costela, A., García-Moreno, I., Bañuelos, J., & López-Arbeloa, I. (2012). Singular laser behavior of hemicyanine dyes: unsurpassed efficiency and finely structured spectrum in the near-IR region. Laser Physics Letters, 9, 426–433. DOI: 10.7452/lapl.201210019.

    Article  CAS  Google Scholar 

  • Chmyrov, A., Sandén, T., & Widengren, J. (2010). Iodide as a fluorescence quencher and promoters: Mechanisms and possible implications. The Journal of Physical Chemistry B, 114, 11282–11291. DOI: 10.1021/jp103837f.

    Article  CAS  Google Scholar 

  • Criado, S., Bertolotti, S. G., Soltermann, A. T., & García, N. A. (1997). Kinetics studies on the photosensitized oxidation (O2(1Δg)-mediated) of tryptophan-alkyl esters in Triton X-100 micellar solutions. Journal of Photochemistry and Photobiology B: Biology, 38, 107–113. DOI: 10.1016/s1011-1344(96)07447-7.

    Article  CAS  Google Scholar 

  • Fromherz, P., & Heilemann, A. (1992). Twisted internal charge transfer in (aminophenyl)pyridinium. The Journal of Physical Chemistry, 96, 6864–6866. DOI: 10.1021/j100196a004.

    Article  CAS  Google Scholar 

  • García-Moreno, I., Costela, A., Martin, V., Pintado-Sierra, M., & Sastre, R. (2009). Materials for a reliable solid-state dye laser at the red spectral edge. Advanced Functional Materials, 19, 2547–2552. DOI: 10.1002/adfm.200900112.

    Article  CAS  Google Scholar 

  • Görner, H., & Gruen, H. (1985). Photophysical properties of quaternary salts of 4-dialkylamino-4′-azastilbenes and their quinolinium analogues in solution: IX. Journal of Photochemistry, 28, 329–350. DOI: 10.1016/0047-2670(85)85036-x.

    Article  Google Scholar 

  • Kim, J. H., & Lee, M. Y. (1999). Excited-state photophysics and dynamics of a hemicyanine dye in AOT reverse micelles. The Journal of Physical Chemistry A, 103, 3378–3382. DOI: 10.1021/jp984167e.

    Article  CAS  Google Scholar 

  • Mishra, A., & Haram, N. S. (2004). New push-pull type dendritic stilbazolium dyes: synthesis, photophysical and electrochemical investigation. Dyes and Pigments, 63, 191–202. DOI: 10.1016/j.dyepig.2004.02.011.

    Article  CAS  Google Scholar 

  • Qin, C. X., Tang, R. C., Chen, B., Chen, D. W., Wang, X. M., & Chen, G. Q. (2010). Study on the dyeing properties of hemicyanine dyes. I. Acrylic fabrics. Fibers and Polymers, 11, 193–198. DOI: 10.1007/s12221-010-0193-7.

    Article  CAS  Google Scholar 

  • Sczepan, M., Rettig, W., Tolmachev, A. I., & Kurdyukov, V. V. (2001). The role of internal twisting in the photophysics of stilbazolium dyes. Physical Chemistry Chemical Physics, 3, 3555–3561. DOI: 10.1039/b102779b.

    Article  CAS  Google Scholar 

  • Shim, T. K., Kim, D. S., Lee, M. H., Rhee, B. K., Cheong, H. M., Kim, H. S., & Yoon, K. B. (2006). Determination of the hyperpolarizability components of hemicyanine dyes by measuring the anisotropic fluorescence and second harmonic of the dyes uniformly aligned within zeolite channels. The Journal of Physical Chemistry B, 110, 16874–16878. DOI: 10.1021/jp062859u.

    Article  CAS  Google Scholar 

  • Strehmel, B., Seifert, H., & Rettig, W. (1997). Photophysical properties of fluorescence probes. 2. A model of multiple fluorescence for stilbazolium dyes studied by global analysis and quantum chemical calculations. The Journal of Physical Chemistry, 101, 2232–2243. DOI: 10.1021/jp962835v.

    Article  CAS  Google Scholar 

  • Valeur, B. (2002). Molecular fluorescence: Principles and applications. Weinheim, Germany: Wiley-VCH.

    Google Scholar 

  • Wilkinson, F., Helman, W. P., & Ross, A. B. (1993). Quantum yields for the photosensitized formation of the lowest electronically excited singlet state of molecular oxygen in solution. Journal of Physical and Chemical Reference Data, 22, 113–262. DOI: 10.1063/1.555934.

    Article  CAS  Google Scholar 

  • Wilkinson, F., Helman, W. P., & Ross, A. B. (1995). Rate constants for the decay and reactions of the lowest electronically excited singlet state of molecular oxygen in solution. An expanded and revised compilation. Journal of Physical and Chemical Reference Data, 24, 663–1021. DOI: 10.1063/1.555965.

    CAS  Google Scholar 

  • Yamaguchi, A., Nakano, M., Nochi, K., Yamashita, T., Morita, K., & Teramae, N. (2006). Longitudinal diffusion behavior of hemicyanine dyes across phospholipid vesicle membranes as studied by second-harmonic generation and fluorescence spectroscopies. Analytical and Bioanalytical Chemistry, 386, 627–632. DOI: 10.1007/s00216-006-0470-x.

    Article  CAS  Google Scholar 

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Correspondence to Daniel O. Mártire or Norman A. García.

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Mártire, D.O., Massad, W., Montejano, H. et al. Properties of singlet- and triplet-excited states of hemicyanine dyes. Chem. Pap. 68, 1137–1140 (2014). https://doi.org/10.2478/s11696-014-0547-5

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  • DOI: https://doi.org/10.2478/s11696-014-0547-5

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