Skip to main content
SpringerLink
Log in

Effects of π-conjugation on the solid-state photoresponsive coloring behavior of bipyridine-boronium complexes

  • Communication
  • Published:
Photochemical & Photobiological Sciences Aims and scope Submit manuscript

Abstract

Solid-state photoinduced coloring of boronium complexes consisting of 9-borabicyclononane and 2,2′-bipyridine with π-conjugated substituents at the 4,4′- or 5,5′-positions was investigated. The substitution position affected the highest occupied molecular orbital distribution and determined the coloring capability. The 4,4′-substituted complexes exhibited coloration upon irradiation, whereas most of the 5,5′-substituted complexes did not.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Notes and references

  1. H. Bouas-Laurent and H. Dürr Pure Appl. Chem. 2001 73 639

    Article  CAS  Google Scholar 

  2. V. I. Minkin Chem. Rev. 2004 104 2751

    Article  CAS  PubMed  Google Scholar 

  3. E. Hadjoudis and I. M. Mavridis Chem. Soc. Rev. 2004 33 579

    CAS  PubMed  Google Scholar 

  4. F. M. Raymo and M. Tomasulo Chem. Soc. Rev. 2005 34 327

    Article  CAS  PubMed  Google Scholar 

  5. R. Pardo, M. Zayat and D. Levy Chem. Soc. Rev. 2011 40 672

    Article  CAS  PubMed  Google Scholar 

  6. M. Natali and S. Giordani Chem. Soc. Rev. 2012 41 4010

    Article  CAS  PubMed  Google Scholar 

  7. F. Pina, M. J. Melo, C. A. T. Laia, A. J. Parola and J. C. Lima Chem. Soc. Rev. 2012 41 869

    Article  CAS  PubMed  Google Scholar 

  8. A. W. King, L. Wang and J. J. Rack Acc. Chem. Res. 2015 48 1115

    Article  CAS  PubMed  Google Scholar 

  9. C.-C. Ko and V. W.-W. Yam Acc. Chem. Res. 2018 51 149

    Article  CAS  PubMed  Google Scholar 

  10. H. Kamogawa and M. Nanasawa Chem. Lett. 1988 17 373

    Article  Google Scholar 

  11. M. Nanasawa and M. Kaneko, H. Kamogawa Bull. Chem. Soc. Jpn. 1993 66 1764

    Article  CAS  Google Scholar 

  12. T. Nagamura Pure Appl. Chem. 1996 68 1449

    Article  CAS  Google Scholar 

  13. R. J. Mortimer Chem. Soc. Rev. 1997 26 147

    Article  CAS  Google Scholar 

  14. J. Wu, C. Tao, Y. Li, J. Li and J. Yu Chem. Sci. 2015 6 2922

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  15. C. Chen, J.-K. Sun, Y.-J. Zhang and X.-D. Yang, J. Zhang Angew. Chem., Int. Ed. 2017 56 14458

    Article  CAS  Google Scholar 

  16. N.-N. Yang, J.-J. Fang, Q. Sui and E.-Q. Gao ACS Appl. Mater. Interfaces 2018 10 2735

    Article  CAS  PubMed  Google Scholar 

  17. P.-Y. Guo, C. Sun, N.-N. Zhang, L.-Z. Cai, M.-S. Wang and G.-C. Guo Chem. Commun. 2018 54 4525

    Article  CAS  Google Scholar 

  18. C. Sun, X.-Q. Yu, M.-S. Wang and G.-C. Guo Angew. Chem., Int. Ed. 2019 58 9475

    Article  CAS  Google Scholar 

  19. S.-L. Li, M. Han, Y. Zhang, G.-P. Li, M. Li, G. He and X.-M. Zhang J. Am. Chem. Soc. 2019 141 12663

    Article  CAS  PubMed  Google Scholar 

  20. W. Dilthey, F. Eduardoff and F. J. Schumacher Justus Liebigs Ann. Chem. 1906 344 300

    Article  CAS  Google Scholar 

  21. O. P. Shitov, S. L. Ioffe, V. A. Tartakovskii and S. S. Novikov Russ. Chem. Rev. 1970 39 905

    Article  Google Scholar 

  22. W. E. Piers, S. C. Bourke and K. D. Conroy Angew. Chem., Int. Ed. 2005 44 5016

    Article  CAS  Google Scholar 

  23. J. M. Lowe, Y. Seo and M. R. Gagné ACS Catal. 2018 8 8192

    Article  CAS  Google Scholar 

  24. B. Rao, C. C. Chong and R. Kinjo J. Am. Chem. Soc. 2018 140 652

    Article  CAS  PubMed  Google Scholar 

  25. Q. Yin, H. F. T. Klare and M. Oestreich Angew. Chem., Int. Ed. 2017 56 3712

    Article  CAS  Google Scholar 

  26. S. J. Geier, C. M. Vogels, N. R. Mellonie, E. N. Daley, A. Decken, S. Doherty and S. A. Westcott Chem. - Eur. J. 2017 23 14485

    Article  CAS  PubMed  Google Scholar 

  27. X. Fan, J. Zheng, Z. H. Li and H. Wang J. Am. Chem. Soc. 2015 137 4916

    Article  CAS  PubMed  Google Scholar 

  28. M. Toure, L. Charles, C. Chendo, S. Viel, O. Chuzel and J.-L. Parrain Chem. - Eur. J. 2016 22 8937

    Article  CAS  PubMed  Google Scholar 

  29. K. Wang, Y. Zhang, D. Chand, D. A. Parrish and J. M. Shreeve Chem. - Eur. J. 2012 18 16931

    Article  CAS  PubMed  Google Scholar 

  30. C. Cui, J. Heilmann-Brohl, A. S. Perucha, M. D. Thomson, H. G. Roskos, M. Wagner and F. Jäkle Macromolecules 2010 43 5256

    Article  CAS  Google Scholar 

  31. M. C. Haberecht, M. Bolte, H.-W. Lerner and M. Wagner Eur. J. Inorg. Chem. 2005 4309

    Google Scholar 

  32. M. D. Thomson, M. Novosel, H. G. Roskos, T. Müller, M. Scheibitz, M. Wagner, F. F. de Biani and P. Zanello J. Phys. Chem. A 2004 108 3281

    Article  CAS  Google Scholar 

  33. L. Ding, K. Ma, G. Dürner, M. Bolte, F. F. de Biani, P. Zanello and M. Wagner J. Chem. Soc., Dalton Trans. 2002 1566

    Google Scholar 

  34. S. Hünig and I. Wehner Heterocycles 1989 28 359

    Article  Google Scholar 

  35. J. Hurmalainen, A. Mansikkamäki, I. S. Morgan, A. Peuronen and H. M. Tuononen Dalton Trans. 2017 46 1377

    Article  CAS  PubMed  Google Scholar 

  36. S. M. Mansell, C. J. Adams, G. Bramham, M. F. Haddow, W. Kaim, N. C. Norman, J. E. McGrady, C. A. Russell and S. J. Udeen Chem. Commun. 2010 46 5070

    Article  CAS  Google Scholar 

  37. T. K. Wood, W. E. Piers, B. A. Keay and M. Parvez Chem. Commun. 2009 5147

    Google Scholar 

  38. W. Kaim Chem. Ber. 1981 114 3789

    Article  CAS  Google Scholar 

  39. J. Yoshino, T. Sekikawa, N. Hatta, N. Hayashi and H. Higuchi Tetrahedron Lett. 2016 57 5489

    Article  CAS  Google Scholar 

  40. N. F. Phelan and M. Orchin J. Chem. Educ. 1968 45 633

    Article  CAS  Google Scholar 

  41. B. E. Tebikachew, F. Edhborg, N. Kann, B. Albinsson and K. Moth-Poulsen Phys. Chem. Chem. Phys. 2018 20 23195

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  42. A. U. Petersen, S. L. Broman, S. T. Olsen and A. S. Hansen, L. Du, A. Kadziola, T. Hansen, H. G. Kjaergaard, K. V. Mikkelsen and M. B. Nielsen Chem. - Eur. J. 2015 21 3968

    Article  CAS  PubMed  Google Scholar 

  43. The oxidation of the counteranion by the S1 state of the cation moiety shown in Scheme S2 † is suggested as a hypothetical reaction in the latter phase in Scheme S1. †

  44. A. Hiltner, R. Y. F. Liu, Y. S. Hu and E. Baer J. Polym. Sci., Part B: Polym. Phys. 2005 43 1047

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Faculty of Science, University of Toyama, 3190 Gofuku, Toyama, Toyama, 930-8555, Japan

    Junro Yoshino & Naoto Hayashi

  2. Department of Chemistry Graduate School of Science and Engineering, University of Toyama, 3190 Gofuku, Toyama, Toyama, 930-8555, Japan

    Junro Yoshino, Yoshito Hirono, Ryota Akahane, Hiroyuki Higuchi & Naoto Hayashi

Authors
  1. Junro Yoshino
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Yoshito Hirono
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Ryota Akahane
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Hiroyuki Higuchi
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Naoto Hayashi
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Junro Yoshino.

Electronic supplementary material

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Yoshino, J., Hirono, Y., Akahane, R. et al. Effects of π-conjugation on the solid-state photoresponsive coloring behavior of bipyridine-boronium complexes. Photochem Photobiol Sci 19, 1517–1521 (2020). https://doi.org/10.1039/d0pp00296h

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1039/d0pp00296h

Search

Navigation