Skip to main content

Advertisement

Log in

Photochemical upconversion and triplet annihilation limit from a boron dipyrromethene emitter

Photochemical & Photobiological Sciences Aims and scope Submit manuscript

Abstract

Non-coherent sensitized red-to-green upconversion has been achieved utilizing platinum(II) tetraphenyltetrabenzoporphyrin (PtTPTBP) as the triplet sensitizer and a nearly quantitatively fluorescent meso-(2,6-dichloropyridyl)-substituted boron dipyrromethene (Cl2PyBODIPY) chromophore (Φ = 0.99 in toluene) as the energy acceptor/annihilator in deoxygenated toluene. Dynamic Stern–Volmer analysis revealed that PtTPTBP phosphorescence as quenched by Cl2PyBODIPY occurs with a KSV of 108 000 M−1, yielding a triplet–triplet energy transfer rate constant of 2.3 × 109 M−1 s−1. Using a non-coherent red light-emitting diode excitation source centered at 626 nm, the incident power dependence responsible for generating singlet BODIPY fluorescence in the green was shown to traverse quadratic to linear regimes, the latter being achieved near 60 mW cm−2. These data were consistent with a photochemical upconversion mechanism being responsible for generating singlet fluorescence from the Cl2PyBODIPY chromophores through sensitized triplet–triplet annihilation (TTA). Integrated delayed fluorescence transients were utilized to reveal the TTA efficiency for the Cl2PyBODIPY chromophore and saturated near 46%, representing the lower limit for the TTA process. Kinetic modelling of the delayed fluorescence transient produced from 1.5 mJ laser pulses (λex = 615 nm) revealed a maximum limiting TTA efficiency of 64% for this upconverting composition, implying that this is indeed an extremely relevant acceptor/annihilator composition for photochemical upconversion.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

Notes and references

  1. T. N. Singh-Rachford, F. N. Castellano, Coord. Chem. Rev., 2010, 254, 2560–2573.

    Article  CAS  Google Scholar 

  2. A. Monguzzi, R. Tubino, S. Hoseinkhani, M. Campione, F. Meinardi, Phys. Chem. Chem. Phys., 2012, 14, 4322–4332.

    Article  CAS  PubMed  Google Scholar 

  3. R. B. Piper, M. Yoshida, D. J. Farrell, T. Khoury, M. J. Crossley, T. W. Schmidt, S. A. Haque, N. J. Ekins-Daukes, RSC Adv., 2014, 4, 8059–8063.

    Article  CAS  Google Scholar 

  4. T. F. Schulze, T. W. Schmidt, Energy Environ. Sci., 2015, 8, 103–125.

    Article  CAS  Google Scholar 

  5. R. W. MacQueen, Y. Y. Cheng, A. N. Danos, K. Lips, T. W. Schmidt, RSC Adv., 2014, 4, 52749–52756.

    Article  CAS  Google Scholar 

  6. M. J. Y. Tayebjee, A. A. Gray-Weale, T. W. Schmidt, J. Phys. Chem. Lett., 2012, 3, 2749–2754.

    Article  CAS  Google Scholar 

  7. T. F. Schulze, J. Czolk, Y.-Y. Cheng, B. Fuckel, R. W. MacQueen, T. Khoury, M. J. Crossley, B. Stannowski, K. Lips, U. Lemmer, A. Colsmann, T. W. Schmidt, J. Phys. Chem. C, 2012, 116, 22794–22801.

    Article  CAS  Google Scholar 

  8. T. F. Schulze, Y. Y. Cheng, B. Fueckel, R. W. MacQueen, A. Danos, N. J. L. K. Davis, M. J. Y. Tayebjee, T. Khoury, R. G. C. R. Clady, N. J. Ekins-Daukes, M. J. Crossley, B. Stannowski, K. Lips, T. W. Schmidt, Aust. J. Chem., 2012, 65, 480–485.

    Article  CAS  Google Scholar 

  9. Y. Y. Cheng, B. Fuckel, R. W. MacQueen, T. Khoury, R. G. C. R. Clady, T. F. Schulze, N. J. Ekins-Daukes, M. J. Crossley, B. Stannowski, K. Lips, T. W. Schmidt, Energy Environ. Sci., 2012, 5, 6953–6959.

    Article  CAS  Google Scholar 

  10. R. S. Khnayzer, J. Blumhoff, J. A. Harrington, A. Haefele, F. Deng, F. N. Castellano, Chem. Commun., 2012, 48, 209–211.

    Article  CAS  Google Scholar 

  11. R. R. Islangulov, F. N. Castellano, Angew. Chem., Int. Ed., 2006, 45, 5957–5959.

    Article  CAS  Google Scholar 

  12. Q. Liu, T. Yang, W. Feng, F. Li, J. Am. Chem. Soc., 2012, 134, 5390–5397.

    Article  CAS  PubMed  Google Scholar 

  13. J.-H. Kim, J.-H. Kim, J. Am. Chem. Soc., 2012, 134, 17478–17481.

    Article  CAS  PubMed  Google Scholar 

  14. T. N. Singh-Rachford, F. N. Castellano, Inorg. Chem., 2009, 48, 2541–2548.

    Article  CAS  PubMed  Google Scholar 

  15. T. N. Singh-Rachford, R. R. Islangulov, F. N. Castellano, J. Phys. Chem. A, 2008, 112, 3906–3910.

    Article  CAS  PubMed  Google Scholar 

  16. T. N. Singh-Rachford, A. Haefele, R. Ziessel, F. N. Castellano, J. Am. Chem. Soc., 2008, 130, 16164–16165.

    Article  CAS  PubMed  Google Scholar 

  17. T. N. Singh-Rachford, F. N. Castellano, J. Phys. Chem. A, 2008, 112, 3550–3556.

    Article  CAS  PubMed  Google Scholar 

  18. T. N. Singh-Rachford, A. Nayak, M. L. Muro-Small, S. Goeb, M. J. Therien, F. N. Castellano, J. Am. Chem. Soc., 2010, 132, 14203–14211.

    Article  CAS  PubMed  Google Scholar 

  19. T. N. Singh-Rachford, F. N. Castellano, J. Phys. Chem. Lett., 2010, 1, 195–200.

    Article  CAS  Google Scholar 

  20. S. Baluschev, T. Miteva, V. Yakutkin, G. Nelles, A. Yasuda, G. Wegner, Phys. Rev. Lett., 2006, 97, 143903.

    Article  CAS  PubMed  Google Scholar 

  21. S. Baluschev, V. Yakutkin, T. Miteva, Y. Avlasevich, S. Chernov, S. Aleshchenkov, G. Nelles, A. Cheprakov, A. Yasuda, K. Muellen, G. Wegner, Angew. Chem., Int. Ed., 2007, 46, 7693–7696.

    Article  CAS  Google Scholar 

  22. A. Turshatov, D. Busko, Y. Avlasevich, T. Miteva, K. Landfester, S. Baluschev, ChemPhysChem, 2012, 13, 3112–3115.

    Article  CAS  PubMed  Google Scholar 

  23. S. Ji, W. Wu, W. Wu, H. Guo, J. Zhao, Angew. Chem., Int. Ed., 2011, 50, 1626–1629.

    Article  CAS  Google Scholar 

  24. J. Sun, F. Zhong, X. Yi, J. Zhao, Inorg. Chem., 2013, 52, 6299–6310.

    Article  CAS  PubMed  Google Scholar 

  25. S. K. Sugunan, U. Tripathy, S. M. K. Brunet, M. F. Paige, R. P. Steer, J. Phys. Chem. A, 2009, 113, 8548–8556.

    Article  CAS  Google Scholar 

  26. F. Deng, J. R. Sommer, M. Myahkostupov, K. S. Schanze, F. N. Castellano, Chem. Commun., 2013, 49, 7406–7408.

    Article  CAS  Google Scholar 

  27. C. E. McCusker, F. N. Castellano, Chem. Commun., 2013, 49, 3537–3539.

    Article  CAS  Google Scholar 

  28. F. Deng, W. Sun, F. N. Castellano, Photochem. Photobiol. Sci., 2014, 13, 813–819.

    Article  CAS  PubMed  Google Scholar 

  29. R. R. Islangulov, D. V. Kozlov, F. N. Castellano, Chem. Commun., 2005, 3776–3778.

    Google Scholar 

  30. D. V. Kozlov, F. N. Castellano, Chem. Commun., 2004, 2860–2861.

    Google Scholar 

  31. W. Zhao, F. N. Castellano, J. Phys. Chem. A, 2006, 110, 11440–11445.

    Article  CAS  PubMed  Google Scholar 

  32. X. Cao, B. Hu, P. Zhang, J. Phys. Chem. Lett., 2013, 4, 2334–2338.

    Article  CAS  Google Scholar 

  33. P. Duan, N. Yanai, N. Kimizuka, Chem. Commun., 2014, 50, 13111–13113.

    Article  CAS  Google Scholar 

  34. A. Monguzzi, J. Mezyk, F. Scotognella, R. Tubino, F. Meinardi, Phys. Rev. B: Condens. Matter, 2008, 78, 195112.

    Article  CAS  Google Scholar 

  35. Y. Y. Cheng, T. Khoury, R. G. C. R. Clady, M. J. Y. Tayebjee, N. J. Ekins-Daukes, M. J. Crossley, T. W. Schmidt, Phys. Chem. Chem. Phys., 2010, 12, 66–71.

    Article  CAS  PubMed  Google Scholar 

  36. Y. Y. Cheng, B. Fueckel, T. Khoury, R. G. C. R. Clady, M. J. Y. Tayebjee, N. J. Ekins-Daukes, M. J. Crossley, T. W. Schmidt, J. Phys. Chem. Lett., 2010, 1, 1795–1799.

    Article  CAS  Google Scholar 

  37. A. Haefele, J. Blumhoff, R. S. Khnayzer, F. N. Castellano, J. Phys. Chem. Lett., 2012, 3, 299–303.

    Article  CAS  Google Scholar 

  38. F. Deng, J. Blumhoff, F. N. Castellano, J. Phys. Chem. A, 2013, 117, 4412–4419.

    Article  CAS  PubMed  Google Scholar 

  39. R. R. Islangulov, J. Lott, C. Weder, F. N. Castellano, J. Am. Chem. Soc., 2007, 129, 12652–12653.

    Article  CAS  PubMed  Google Scholar 

  40. T. N. Singh-Rachford, J. Lott, C. Weder, F. N. Castellano, J. Am. Chem. Soc., 2009, 131, 12007–12014.

    Article  CAS  PubMed  Google Scholar 

  41. Y. C. Simon, C. Weder, J. Mater. Chem., 2012, 22, 20817–20830.

    Article  CAS  Google Scholar 

  42. A. Monguzzi, M. Frigoli, C. Larpent, R. Tubino, F. Meinardi, Adv. Funct. Mater., 2012, 22, 139–143.

    Article  CAS  Google Scholar 

  43. A. Monguzzi, R. Tubino, F. Meinardi, J. Phys. Chem. A, 2009, 113, 1171–1174.

    Article  CAS  PubMed  Google Scholar 

  44. J.-H. Kim, F. Deng, F. N. Castellano, J.-H. Kim, Chem. Mater., 2012, 24, 2250–2252.

    Article  CAS  Google Scholar 

  45. J.-H. Kim, F. Deng, F. N. Castellano, J.-H. Kim, ACS Photonics, 2014, 1, 382–388.

    Article  CAS  Google Scholar 

  46. P. E. Keivanidis, S. Baluschev, T. Miteva, G. Nelles, U. Scherf, A. Yasuda, G. Wegner, Adv. Mater., 2003, 15, 2095–2098.

    Article  CAS  Google Scholar 

  47. S. Baluschev, J. Jacob, Y. S. Avlasevich, P. E. Keivanidis, T. Miteva, A. Yasuda, G. Nelles, A. C. Grimsdale, K. Muellen, G. Wegner, ChemPhysChem, 2005, 6, 1250–1253.

    Article  CAS  PubMed  Google Scholar 

  48. S. Baluschev, P. E. Keivanidis, G. Wegner, J. Jacob, A. C. Grimsdale, K. Muellen, T. Miteva, A. Yasuda, G. Nelles, Appl. Phys. Lett., 2005, 86, 061904.

    Article  CAS  Google Scholar 

  49. A. J. Svagan, D. Busko, Y. Avlasevich, G. Glasser, S. Baluschev, K. Landfester, ACS Nano, 2014, 8, 8198–8207.

    Article  CAS  PubMed  Google Scholar 

  50. F. Marsico, A. Turshatov, R. Pekoez, Y. Avlasevich, M. Wagner, K. Weber, D. Donadio, K. Landfester, S. Baluschev, F. R. Wurm, J. Am. Chem. Soc., 2014, 136, 11057–11064.

    Article  CAS  PubMed  Google Scholar 

  51. C. Wohnhaas, K. Friedemann, D. Busko, K. Landfester, S. Baluschev, D. Crespy, A. Turshatov, ACS Macro Lett., 2013, 2, 446–450.

    Article  CAS  Google Scholar 

  52. P. E. Keivanidis, F. Laquai, J. W. F. Robertson, S. Baluschev, J. Jacob, K. Mullen, G. Wegner, J. Phys. Chem. Lett., 2011, 2, 1893–1899.

    Article  CAS  Google Scholar 

  53. C. Zhang, J. Y. Zheng, Y. S. Zhao, J. Yao, Chem. Commun., 2010, 46, 4959–4961.

    Article  CAS  Google Scholar 

  54. V. Jankus, E. W. Snedden, D. W. Bright, V. L. Whittle, J. A. G. Williams, A. Monkman, Adv. Funct. Mater., 2013, 23, 384–393.

    Article  CAS  Google Scholar 

  55. X. Yu, X. Cao, X. Chen, N. Ayres, P. Zhang, Chem. Commun., 2015, 51, 588–591.

    Article  CAS  Google Scholar 

  56. P. Duan, N. Yanai, H. Nagatomi, N. Kimizuka, J. Am. Chem. Soc., 2015, 137, 1887–1894.

    Article  CAS  PubMed  Google Scholar 

  57. P. Duan, N. Yanai, N. Kimizuka, J. Am. Chem. Soc., 2013, 135, 19056–19059.

    Article  CAS  PubMed  Google Scholar 

  58. T. W. Schmidt, F. N. Castellano, J. Phys. Chem. Lett., 2014, 5, 4062–4072.

    Article  CAS  PubMed  Google Scholar 

  59. W. Wu, X. Cui, J. Zhao, Chem. Commun., 2013, 49, 9009–9011.

    Article  CAS  Google Scholar 

  60. C. A. Parker, C. G. Hatchard, Proc. Chem. Soc., London, 1962, 386–387.

    Google Scholar 

  61. T. N. Singh-Rachford, F. N. Castellano, J. Phys. Chem. A, 2009, 113, 5912–5917.

    Article  CAS  PubMed  Google Scholar 

  62. S. Guo, W. Wu, H. Guo, J. Zhao, J. Org. Chem., 2012, 77, 3933–3943.

    Article  CAS  PubMed  Google Scholar 

  63. D. Huang, J. Sun, L. Ma, C. Zhang, J. Zhao, Photochem. Photobiol. Sci., 2013, 12, 872–882.

    Article  CAS  PubMed  Google Scholar 

  64. X. Cui, J. Zhao, Y. Zhou, J. Ma, Y. Zhao, J. Am. Chem. Soc., 2014, 136, 9256–9259.

    Article  CAS  PubMed  Google Scholar 

  65. J. Bartelmess, W. W. Weare, N. Latortue, C. Duong, D. S. Jones, New J. Chem., 2013, 37, 2663–2668.

    Article  CAS  Google Scholar 

  66. K. G. Casey, E. L. Quitevis, J. Phys. Chem., 1988, 92, 6590–6594.

    Article  CAS  Google Scholar 

  67. S. L. Murov, I. Carmichael and G. L. Hug, Handbook of Photochemistry, Marcel Dekker, Inc., 2nd edn, 1993.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to F. N. Castellano.

Additional information

Electronic supplementary information (ESI) available. See DOI: 10.1039/c5pp00106d

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Deng, F., Francis, A.J., Weare, W.W. et al. Photochemical upconversion and triplet annihilation limit from a boron dipyrromethene emitter. Photochem Photobiol Sci 14, 1265–1270 (2015). https://doi.org/10.1039/c5pp00106d

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1039/c5pp00106d

Navigation