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Femtosecond excited state dynamics of stilbene–viologen complexes with a weakly pronounced charge transfer

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Abstract

The femtosecond dynamics of photoinduced electron transfers in supramolecular donor-acceptor complexes between (E)-bis(18-crown-6)stilbene (D) and tetraperchlorates of 2,7-di(2-ammonioethyl)(2,7-dia-zapyrenium) (A1), 3,3’-(E)-ethene–1,2-diylbis[1-(3-ammoniopropyl)pyridinium] (A2) and 4,4’-ethane-1,2-diylbis[1-(3-ammoniopropyl)pyridinium] (A3) was studied. The acceptors A2 and A3 are weak electron acceptors whose first reduction potentials are equal to –1.0 and –1.2 V. (Ag), respectively, while A1 is a strong acceptor with a reduction potential of –0.42 V. It was shown that the back electron transfer time in CT-states of the complexes D A2 and D A3 is 30–40 ps, which is approximately 50 times greater than the analogous time for the charge transfer complexes studied earlier. The complex D A1 is characterized by ultrafast back electron transfer (770 fs). The relaxation pathway of excited states of D A1 depends on the wavelength of the excitation light. When excited at 356 nm, the accumulation of a transient locally excited (LE) state with a 250 fs lifetime was observed. But when excited at 425 nm, the formation of the LE-state was not observed.

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References

  1. T. L. Mako, J. M. Racicot and M. Levine, Supramolecular luminescent sensors, Chem. Rev., 2019, 119, 322–477.

    Article  CAS  PubMed  Google Scholar 

  2. A. S. Lukas and M. R. Wasielewski, Approaches to a molecular switch using photoinduced electron and energy transfer, in Molecular Switches, ed. B. L. Feringa, Wiley-VCH Verlag, GmbH, 2001, pp. 1–36.

  3. T. Nabeshima and D. Nishida, Control of binding affinity to paraquat by novel macrocyclic systems responding to redox reactions, Tetrahedron Lett., 2002, 43, 5719–5722.

    Article  CAS  Google Scholar 

  4. J.-Y. Li, M.-L. Peng, L.-P. Zhang, L.-Zh. Wu, B.-J. Wang and Ch.-H. Tung, Long-lived photoinduced charge separation in carbazole–pyrene–viologen system incorporated in Langmuir-Blodgett films of substituted diazacrown ethers, J. Photochem. Photobiol., A, 2002, 150, 101–108.

    Article  CAS  Google Scholar 

  5. N. A. Romero and D. A. Nicewicz, Organic photoredox catalysis, Chem. Rev., 2016, 116, 10075–10166.

    Article  CAS  PubMed  Google Scholar 

  6. A. C. Benniston and A. Harriman, Artificial photosynthesis, Mater. Today, 2008, 11, 26–34.

    Article  CAS  Google Scholar 

  7. M. D. Karkas, E. V. Johnston, O. Verho and B. Åkermark, Artificial photosynthesis: from nanosecond electron transfer to catalytic water oxidation, Acc. Chem. Res., 2014, 47, 100–111.

    Article  PubMed  CAS  Google Scholar 

  8. L. Antusch, N. Gaß and H.-A. Wagenknecht, Elucidation of the Dexter-type energy transfer in DNA by thymine–thymine dimer formation using photosensitizers as artificial nucleosides, Angew. Chem., Int. Ed., 2016, 55, 1–6.

    Article  CAS  Google Scholar 

  9. J. C. Genereux and J. K. Barton, Mechanisms for DNA charge transport, Chem. Rev., 2010, 110, 1642–1662.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  10. M. K. Brennaman, C. N. Fleming, Ch. A. Slate, S. A. Serron, S. E. Bettis, B. W. Erickson, J. M. Papanikolas and Th. J. Meyer, Distance dependence of intrahelix RuII* to OsII polypyridyl excited-state energy transfer in oligoproline assemblies, J. Phys. Chem. B, 2013, 117, 6352–6363.

    Article  CAS  Google Scholar 

  11. J. Chen, M. Kuss-Petermann and O. S. Wenger, Distance dependence of bidirectional concerted proton-electron transfer in phenol-Ru(2,2′-bipyridine)32+ dyads, Chem. –Eur. J., 2014, 20, 4098–4104.

    Article  CAS  PubMed  Google Scholar 

  12. A. Nielsen, G. Kuzmanich and M. A. Garcia-Garibay, Solid state and their distance-dependence in solution reveal a Dexter S2–S2 energy-transfer mechanism, J. Phys. Chem. A, 2014, 118, 1858–1863.

    Article  CAS  Google Scholar 

  13. F. D’Souza, E. Maligaspe, A. S. D. Sandanayaka, N. K. Subbaiyan, P. A. Karr, T. Hasobe and O. Ito, Photochemical charge separation in supramolecular phthalocyanine-multifullerene conjugates assembled by crown ether-alkyl ammonium cation interactions, J. Phys. Chem. A, 2010, 114, 10951–10959.

    Article  CAS  Google Scholar 

  14. J.-F. Xu, Y.-Zh. Chen, L.-Zh. Wu, Ch.-H. Tung and Q.-Z. Yang, Synthesis of a photoresponsive cryptand and its complexations with paraquat and 2,7-diazapyrenium, Org. Lett., 2014, 16, 684–687.

    Article  CAS  PubMed  Google Scholar 

  15. P. L. Anelli, N. Spencer and J. F. Stoddart, Diazadibenzo-30-crown-10 derivatives as receptors for diquat, Tetrahedron Lett., 1988, 29, 1569–1572.

    Article  CAS  Google Scholar 

  16. F. Huang, L. N. Zakharov, A. L. Rheingold, M. Ashraf-Khorassani and H. W. Gibson, Synthesis of a symmetric cylindrical bis(crown ether) host and its complexation with paraquat, J. Org. Chem., 2005, 70, 809–813.

    Article  CAS  Google Scholar 

  17. F. Huang, P. Gantzel, D. S. Nagvekar, A. L. Rheingold and H. W. Gibson, Taco grande: a dumbbell bis(crown ether)/paraquat [3](taco complex), Tetrahedron Lett., 2006, 47, 7841–7844.

    Article  CAS  Google Scholar 

  18. M. Zhang, K. Zhu and F. Huang, Improved complexation of paraquat derivatives by the formation of crown ether-based cryptands, Chem. Commun., 2010, 46, 8131–8141.

    Article  CAS  Google Scholar 

  19. R. S. Forgan, Ch. Wang, D. C. Friedman, J. M. Spruell, Ch. L. Stern, A. A. Sarjeant, D. Cao and J. F. Stoddart, Donor–acceptor ring-in-ring complexes, Chem. –Eur. J., 2012, 18, 202–212.

    Article  CAS  PubMed  Google Scholar 

  20. T. Kuwabara, M. Sugiyama, K. Takeuchi and H. Sakane, Catenane and inclusion complex as photochromic compounds involving viologen units, J. Photochem. Photobiol., A, 2013, 269, 59–64.

    Article  CAS  Google Scholar 

  21. A. M. Brun and A. Harriman, Dynamics of electron transfer between intercalated polycyclic molecules: effect of interspersed bases, J. Am. Chem. Soc., 1992, 114, 3656–3660.

    Article  CAS  Google Scholar 

  22. T. Fiebig, Ch. Wan, Sh. O. Kelley, J. K. Barton and A. H. Zewail, Femtosecond dynamics of the DNA intercalator ethidium and electron transfer with mononucleotides in water, Proc. Natl. Acad. Sci. U. S. A., 1999, 96, 1187–1192.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  23. A. I. Kononov, E. B. Moroshkina, N. V. Tkachenko and H. Lemmetyinen, Photophysical processes in the complexes of DNA with ethidium bromide and acridine orange: a femtosecond study, J. Phys. Chem. B, 2001, 105, 535–541.

    Article  CAS  Google Scholar 

  24. M. V. Fomina, A. S. Nikiforov, A. I. Vedernikov, N. A. Kurchavov and S. P. Gromov, Self-assembly of supra-molecular complexes of cyanine dyes containing terminal ammonium groups with bis(18-crown-6)stiIbene, Mendeleev Commun., 2014, 24, 295–297.

    Article  CAS  Google Scholar 

  25. E. N. Ushakov, T. P. Martyanov, A. I. Vedernikov, S. K. Sazonov, I. G. Strelnikov, L. S. Klimenko, M. V. Alfimov and S. P. Gromov, Stereospecific [2 + 2]-cross-photocycloaddition in a supramolecular donor-acceptor complex, Tetrahedron Lett., 2019, 60, 150–153.

    Article  CAS  Google Scholar 

  26. E. V. Lukovskaya, A. A. Kosmacheva, O. A. Fedorova, A. A. Bobyleva, A. V. Dolganov, N. E. Shepel’, Yu. V. Fedorov, V. V. Novikov and A. V. Anisimov, Synthesis of chromophoric crown-containing styryl derivative of terthiophene and its complexation with octane-1,8-diaminium diperchlorate, Russ. J. Org. Chem., 2014, 50, 552–558.

    Article  CAS  Google Scholar 

  27. M. Sisido, S. Hoshino, H. Kusano, M. Kuragaki, M. Makino, H. Sasaki, T. A. Smith and K. P. Ghiggino, Distance dependence of photoinduced electron transfer along α-helical polypeptides, J. Phys. Chem. B, 2001, 105, 10407–10415.

    Article  CAS  Google Scholar 

  28. E. N. Ushakov, S. P. Gromov, A. I. Vedernikov, E. V. Malysheva, A. A. Botsmanova, M. V. Alfimov, B. Eliasson, U. G. Edlund, J. K. Whitesell and M. A. Fox, Self-organization of highly stable electron donor-acceptor complexes via host-guest Interactions, J. Phys. Chem. A, 2002, 106, 2020–2023.

    Article  CAS  Google Scholar 

  29. S. P. Gromov, E. N. Ushakov, A. I. Vedernikov, N. A. Lobova, M. V. Alfimov, Yu. A. Strelenko, J. K. Whitesell and M. A. Fox, A novel optical sensor for metal ions based on ground-state intermolecular charge-transfer complexation, Org. Lett., 1999, 1, 1697–1699.

    Article  CAS  Google Scholar 

  30. K. P. Butin, A. A. Moiseeva, S. P. Gromov, A. I. Vedernikov, A. A. Botsmanova, E. N. Ushakov and M. V. Alfimov, Prospects of electroanalytical investigations of supramolecular complexes of a bis-crown stilbene with viologen-like compounds bearing two ammonioalkyl groups, J. Electroanal. Chem., 2003, 547, 93–102.

    Article  CAS  Google Scholar 

  31. I. S. Alaverdian, A. V. Feofanov, S. P. Gromov, A. I. Vedernikov, N. A. Lobova and M. V. Alfimov, Structure of charge-transfer complexes formed by bis-crown stilbene and dipyridylethylene derivatives as probed by surface-enhanced Raman scattering spectroscopy, J. Phys. Chem. A, 2003, 107, 9542–9546.

    Article  CAS  Google Scholar 

  32. E. N. Ushakov, V. A. Nadtochenko, S. P. Gromov, A. I. Vedernikov, N. A. Lobova, M. V. Alfimov, F. E. Gostev, A. N. Petrukhin and O. M. Sarkisov, Ultrafast excited state dynamics of the bi- and termolecular stilbene-viologen charge-transfer complexes assembled via host–guest interactions, Chem. Phys., 2004, 298, 251–261.

    Article  CAS  Google Scholar 

  33. Yu. S. Alaverdyan, A. V. Feofanov, S. P. Gromov, A. I. Vedernikov, N. A. Lobova and M. V. Alfimov, Spectroscopy of surface-enhanced Raman scattering of a complex with charge transfer between a bis-crown-containing stilbene and a bis-ammonium-alkyl derivative of dipyridylethylene, Opt. Spectrosc, 2004, 97, 560–566.

    Article  CAS  Google Scholar 

  34. S. P. Gromov, A. I. Vedernikov, E. N. Ushakov, N. A. Lobova, A. A. Botsmanova, L. G. Kuz’mina, A. V. Churakov, Yu. A. Strelenko, M. V. Alfimov, J. A. K. Howard, D. Johnels and U. G. Edlund, Novel supramolecular charge-transfer systems based on bis(18-crown-6)stilbene and viologen analogues bearing two ammonioalkyl groups, New J. Chem., 2005, 29, 881–894.

    Article  CAS  Google Scholar 

  35. A. I. Vedernikov, L. G. Kuz’mina, N. A. Lobova, E. N. Ushakov, J. A. K. Howard, M. V. Alfimov and S. P. Gromov, Unusual three-decker structure of a D–A–D complex between bis(crown)stilbene and a di(quinolyl) ethylene derivative, Mendeleev Commun., 2007, 17, 151–153.

    Article  CAS  Google Scholar 

  36. S. P. Gromov, A. I. Vedernikov, E. N. Ushakov and M. V. Alfimov, Unusual supramolecular donor-acceptor complexes of bis(crown)stiIbenes and bis(crown)azo-benzene with viologen analogs, Russ. Chem. Bull, 2008, 57, 793–801.

    Article  CAS  Google Scholar 

  37. A. I. Vedernikov, E. N. Ushakov, A. A. Efremova, L. G. Kuz’mina, A. A. Moiseeva, N. A. Lobova, A. V. Churakov, Yu. A. Strelenko, M. V. Alfimov, J. A. K. Howard and S. P. Gromov, Synthesis, structure, and properties of supramolecular charge-transfer complexes between bis(18-crown-6)stilbene and ammonioalkyl derivatives of 4,4′-bipyridine and 2,7-diazapyrene, J. Org. Chem., 2011, 76, 6768–6779.

    Article  CAS  Google Scholar 

  38. V. V. Volchkov, M. N. Khimich, M. V. Rusalov, F. E. Gostev, I. V. Shelaev, V. A. Nadtochenko, A. I. Vedernikov, S. P. Gromov, A. Ya. Freidzon, M. V. Alfimov and M. Ya. Melnikov, Formation of supramolecular charge-transfer complex. Ultrafast excited state dynamics and quantum-chemical calculations, Photochem. Photobiol. Sci., 2019, 18, 232–241.

    Article  CAS  PubMed  Google Scholar 

  39. M. V. Rusalov, V. V. Volchkov, V. L. Ivanov, M. Ya. Melnikov, F. E. Gostev, V. A. Nadtochenko, A. I. Vedernikov, S. P. Gromov and M. V. Alfimov, Ultrafast excited state dynamics of a stilbene–viologen charge transfer complex and its interaction with alkanediammonium salts, J. Photochem. Photobiol., A, 2019, 372, 89–98.

    Article  CAS  Google Scholar 

  40. M. V. Rusalov, V. V. Volchkov, V. L. Ivanov, M. Ya. Melnikov, I. V. Shelaev, F. E. Gostev, V. A. Nadtochenko, A. I. Vedernikov, S. P. Gromov and M. V. Alfimov, Femtosecond excited state dynamics of a stilbene-viologene charge transfer complex assembled via host-guest interactions, Photochem. Photobiol. Sci., 2017, 16, 1800–1811.

    Article  Google Scholar 

  41. V. V. Volchkov, M. V. Rusalov, F. E. Gostev, I. V. Shelaev, V. A. Nadtochenko, A. I. Vedernikov, A. A. Efremova, L. G. Kuz’mina, S. P. Gromov, M. V. Alfimov and M. Ya. Melnikov, Complexation of bis-crown stilbene with alkali and alkaline-earth metal cations. Ultrafast excited state dynamics of the stilbene-viologen analogue charge transfer complex, J. Phys. Org. Chem., 2018, 31, e3759.

  42. R. Masrat, M. Maswal and A. A. Dar, Competitive solubilization of naphthalene and pyrene in various micellar systems, J. Hazard. Mater., 2013, 244–245, 662–670.

  43. M. D’Abramo, M. Aschi and A. Amadei, Theoretical calculation of the pyrene emission properties in different solvents, Chem. Phys. Lett., 2015, 639, 17–22.

    Article  CAS  Google Scholar 

  44. W. Wei, C. Xu, J. Ren, B. Xu and X. Qu, Sensing metal ions with ion selectivity of a crown ether and fluorescence resonance energy transfer between carbon dots and graphene, Chem. Commun., 2012, 48, 1284–1286.

    Article  CAS  Google Scholar 

  45. J. S. Baskin, H.-Zh. Yu and A. H. Zewail, Ultrafast dynamics of porphyrins in the condensed phase: I. Free base tetra-phenylporphyrin, J. Phys. Chem. A, 2002, 106, 9837–9844.

    Article  CAS  Google Scholar 

  46. N. V. Bashmakova, Ye. O. Shaydyuk, S. M. Levchenko, A. E. Masunov, O. V. Przhonska, J. L. Bricks, O. D. Kachkovsky, Yu. L. Slominsky, Yu. P. Piryatinski, K. D. Belfield and M. V. Bondar, Design and electronic structure of new styryl dye bases: steady-state and time-resolved spectroscopic studies, J. Phys. Chem. A, 2014, 118, 4502–4509.

    Article  CAS  Google Scholar 

  47. O. A. Khakhel, Absorption spectra of pyrene aggregates in saturated solutions, J. Appl. Spectrosc, 2001, 68, 280–286.

    Article  CAS  Google Scholar 

  48. D. A. Van Dyke, B. A. Pryor, Ph. G. Smith and M. R. Topp, Nanosecond time-resolved fluorescence spectroscopy in the physical chemistry laboratory: formation of the pyrene excimer in solution, J. Chem. Educ., 1998, 75, 615–620.

    Article  Google Scholar 

  49. H. Miyasaka, H. Masuhara and N. Mataga, Picosecond absorption spectra and relaxation processes of the excited singlet state of pyrene in solution, Laser Chem., 1983, 1, 357–386.

    Article  CAS  Google Scholar 

  50. K. Yoshihara, T. Kasuya, A. Inoue and S. Nagakura, Time resolved spectra of pyrene excimer and pyrene-dimethyl-aniline exciplex, Chem. Phys. Lett., 1971, 9, 469–472.

    Article  CAS  Google Scholar 

  51. B. S. Brunschwig and N. Sutin, Rate-constant expressions for nonadiabatic electron-transfer reactions, Comment. Inorg. Chem., 1987, 6, 209–235.

    Article  CAS  Google Scholar 

  52. H. Sumi and R. A. Marcus, Dynamical effects in electron transfer reactions, J. Chem. Phys., 1986, 84, 4894–4914.

    CAS  Google Scholar 

  53. P. F. Barbara, T. J. Meyer and M. A. Ratner, Contemporary issues in electron transfer research, J. Phys. Chem., 1996, 100, 13148–13168.

    Article  CAS  Google Scholar 

  54. A. I. Vedernikov, L. G. Kuz’mina, A. A. Botsmanova, Y. A. Strelenko, J. A. K. Howard, M. V. Alfimov and S. P. Gromov, Stacking structures of complexes between bis (crown)azobenzene and a dipyridylethylene derivative in a crystal and in solution, Mendeleev Commun., 2007, 17, 148–150.

    Article  CAS  Google Scholar 

  55. E. N. Ushakov, T. P. Martyanov, A. I. Vedernikov, S. K. Sazonov, I. G. Strelnikov, L. S. Klimenko, M. V. Alfimov and S. P. Gromov, Stereospecific [2 + 2]-cross-photocycloaddition in a supramolecular donor-acceptor complex, Tetrahedron Lett., 2019, 60, 150–153.

    Article  CAS  Google Scholar 

  56. A. I. Vedernikov, S. S. Basok, S. P. Gromov, L. G. Kuz’mina, V. G. Avakyan, N. A. Lobova, E. Yu. Kulygina, T. V. Titkov, Yu. A. Strelenko, E. I. Ivanov, J. A. K. Howard and M. V. Alfimov, Synthesis and structure of bis-crown-containing stilbenes, Russ. J. Org. Chem., 2005, 41, 843–854.

    Article  CAS  Google Scholar 

  57. S. P. Gromov, A. I. Vedernikov, L. G. Kuz’mina, N. A. Lobova, S. S. Basok, Yu. A. Strelenko and M. V. Alfimov, Stereoselective [2 + 2] photocycloaddition in bispseudosandwich complexes of bis(18-crown-6) stilbene with alkanediammonium ions, Russ. Chem. Bull, 2009, 58, 108–114.

    Article  CAS  Google Scholar 

  58. W. H. Melhuish, Quantum efficiencies of fluorescence of organic substances - effect of solvent and concentration of fluorescence solute, J. Phys. Chem., 1961, 65, 229–235.

    Article  CAS  Google Scholar 

  59. M. V. Rusalov, Numerical simulation of chemical equilibria and photostationary states using spectrophotometric and spectrofluorometric data, Russ. J. Gen. Chem., 2005, 75, 351–358.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Chemistry Department, M. V. Lomonosov Moscow State University, Leninskie Gory 1-3, 119991, Moscow, Russian Federation

    Mikhail V. Rusalov, Valery V. Volchkov, Vladimir L. Ivanov, Mikhail Ya. Melnikov, Victor A. Nadtochenko & Sergey P. Gromov

  2. N. N. Semenov Institute of Chemical Physics, Russian Academy of Sciences, Kosygina str. 4, 119991, Moscow, Russian Federation

    Fedor E. Gostev, Ivan V. Shelaev & Victor A. Nadtochenko

  3. Photochemistry Center, Federal Scientific Research Center “Crystallography and Photonics”, Russian Academy of Sciences, Novatorov str. 7A-1, 119421, Moscow, Russian Federation

    Artem I. Vedernikov, Sergey P. Gromov & Michael V. Alfimov

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  1. Mikhail V. Rusalov
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  2. Valery V. Volchkov
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Electronic supplementary information (ESI) available: Transient absorption spectra of D, A1, A2, A3, D•A1•D and D•A3. See DOI: 10.1039/D0PP00034E

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Rusalov, M.V., Volchkov, V.V., Ivanov, V.L. et al. Femtosecond excited state dynamics of stilbene–viologen complexes with a weakly pronounced charge transfer. Photochem Photobiol Sci 19, 1189–1200 (2020). https://doi.org/10.1039/d0pp00034e

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