Skip to main content
Log in

Structure and electronics in dimeric boron π expanded azine and salphen complexes

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

Abstract

Although boron-based fluorophores incorporating nitrogenous chelating ligands have received much attention, there has been little work on examples of boron-salphen and azine derivatives. In this report, we present several it expanded boron salphen type complexes, incorporating both bis(2-hydroxy-naphthaldehyde)azine as well as ortho, meta and para variants of the analogous 2-hydroxynaphthalde-hyde salphen compounds. For the azine, we observed only the formation of a single BF2 adduct, while for the naphth-phen compounds dimeric BF2 binding was observed. All new compounds were fully characterized via X-ray diffraction, and both DFT. and TDDFT. studies were carried out to probe the electronic structures of these fluorophores

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.

Similar content being viewed by others

References

  1. M. S. T. Goncalves, Chem. Rev., 2009, 109, 190–212.

    Article  CAS  PubMed  Google Scholar 

  2. M. Vendrell, D. Zhai, J. C. Er and Y. Chang, Chem. Rev., 2012, 112, 439–4420.

    Article  CAS  Google Scholar 

  3. Y. Jeong and J. Yoon, Inorg. Chim. Acta, 2012, 381, 2–14.

    Article  CAS  Google Scholar 

  4. A. Hagfeldt, G. Boschloo, L. Sun, L. Kloo and H. Pettersson, Chem. Rev., 2010, 110, 6595–6663.

    Article  CAS  PubMed  Google Scholar 

  5. H. Zheng, Z.-Q. Zhan, Q.-N. Bian and X.-J. Zhang, Chem. Commun., 2013, 49, 429–447.

    Article  CAS  Google Scholar 

  6. J. Han and K. Burgess, Chem. Rev., 2010, 110, 2709–2728.

    Article  CAS  PubMed  Google Scholar 

  7. L. D. Lavis and R. T. Raines, ACS. Chem. Biol, 2008, 3, 142–155.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  8. A. Mishra, M. K. R. Fischer and R. Bauerle, Angew. Chem., Int. Ed., 2009, 48, 2474–2499.

    Article  CAS  Google Scholar 

  9. A. Loudet and K. Burgess, Chem. Rev., 2007, 107, 4891–4932.

    Article  CAS  PubMed  Google Scholar 

  10. R. Ziessel, G. Ulrich and A. Harriman, New J. Chem., 2007, 31, 496–501.

    Article  CAS  Google Scholar 

  11. G. Ulrich, R. Ziessel and A. Harriman, Angew. Chem., Int. Ed., 2008, 47, 1184–1201.

    Article  CAS  Google Scholar 

  12. N. Boens, V. Leen and W. Dehaen, Chem. Soc. Rev., 2012, 41, 1130.

    Article  CAS  PubMed  Google Scholar 

  13. A. Y. Bochkov, I. O. Akchurin, O. A. Dyachenko and V. F. Traven, Chem. Commun., 2013, 49, 11653–11655.

    Article  CAS  Google Scholar 

  14. H. Lu, J. Mack, Y. Yang and Z. Shen, Chem. Soc. Rev., 2014, 43, 4778–4823.

    Article  CAS  PubMed  Google Scholar 

  15. S. M. Barbon, J. T. Price, U. Yogarajah and J. B. Gilroy, RSC. Adv., 2015, 5, 56316–56324.

    Article  CAS  Google Scholar 

  16. M. Nakamura, H. Tahara, K. Takahashi, T. Nagata, H. Uoyama, D. Kuzuhara, S. Mori, T. Okujima, H. Yamada and H. Uno, Org. Biomol. Chem., 2012, 10, 6840–8649.

    Article  CAS  PubMed  Google Scholar 

  17. M. T. Whited, N. M. Patel, S. T. Roberts, K. Allen, P. I. Djurovich, S. E. Bradforth and M. E. Thompson, Chem. Commun., 2012, 48, 284–286.

    Article  CAS  Google Scholar 

  18. L. Wang, I.-S. Tamgho, L. Crandall, J. Rack and C. Ziegler, Phys. Chem. Chem. Phys., 2014, 4–6.

    Google Scholar 

  19. C. Yu, L. Jiao, P. Zhang, Z. Feng, C. Cheng, Y. Wei, X. Mu and E. Hao, Org. Lett, 2014, 16, 3048–3051.

    Article  CAS  PubMed  Google Scholar 

  20. H. M. Rhoda, K. Chanawanno, A. J. King, Y. V. Zatsikha, C. J. Ziegler and V. N. Nemykin, Chem. - Eur. J., 2015, 21, 18043–18046.

    Article  CAS  PubMed  Google Scholar 

  21. J. Wang, Q. Wu, C. Yu, Y. Wei, X. Mu, E. Hao and L. Jiao, J. Org. Chem., 2016, 81, 11316–11323.

    Article  CAS  PubMed  Google Scholar 

  22. L. Zhou, D. Xu, H. Gao, C. Zhang, F. Ni, W. Zhao, D. Cheng, X. Liu and A. Han,J. Org. Chem., 2016, 81, 7439–7447.

    Article  CAS  PubMed  Google Scholar 

  23. I. S. Tamgho, A. Hasheminasab, J. T. Engle, V. N. Nemykin and C. J. Ziegler, J. Am. Chem. Soc, 2014, 136, 5623–5626.

    Article  CAS  PubMed  Google Scholar 

  24. H.-J. Li, W.-F. Fu, L. Li, X. Gan, W.-H. Mu, W. Chen, X.-M. Duan and H.-B. Song, Org. Lett, 2010, 12, 2924–2927.

    Article  CAS  PubMed  Google Scholar 

  25. G. Nawn, S. R. Oakley, M. B. Majewski, R. McDonald, B. O. Patrick and R. G. Hicks, Chem. Sci., 2013, 4, 612–621.

    Article  CAS  Google Scholar 

  26. A. Combes, C. R. Acad. Fr., 1889, 108, 1252.

    Google Scholar 

  27. L. Canali and D. C. Sherrington, Chem. Soc. Rev., 1999, 28, 85–93.

    Article  CAS  Google Scholar 

  28. P. G. Cozzi, Chem. Soc. Rev., 2004, 33, 410–421.

    Article  CAS  PubMed  Google Scholar 

  29. C. J. Whiteoak, G. Salassa and A. Kleij, Chem. Soc. Rev., 2012, 41, 622–631.

    Article  CAS  PubMed  Google Scholar 

  30. R. M. Clarke and T. Storr, Dalton Trans., 2014, 43, 9380–9391.

    Article  CAS  PubMed  Google Scholar 

  31. S. J. Wezenberg and A. W. Kleij, Angew. Chem., Int. Ed., 2008, 47, 2354–2364.

    Article  CAS  Google Scholar 

  32. H. Kunkely and A. Vogler, Inorg. Chim. Acta, 2001, 321, 171–174.

    Article  CAS  Google Scholar 

  33. S. Dagorne and D. A. Atwood, Chem. Rev., 2008, 108, 4037–4071.

    Article  CAS  PubMed  Google Scholar 

  34. P. Wei and D. A. Atwood, Inorg. Chem., 1997, 36, 4060–4065.

    Article  CAS  Google Scholar 

  35. F. Umland, E. Hohaus and K. Brodte, Chem. Ber., 1973, 106, 2427–2437.

    Article  CAS  Google Scholar 

  36. P. Gong, H. Yang, J. Sun, Z. Zhang, J. Sun, P. Xue and R. Lu, J. Mater. Chem. C, 2015, 3, 10302–10308.

    Article  CAS  Google Scholar 

  37. Q. Hou, L. Zhao, H. Zhang, Y. Wang and S. Jiang,J. Lumin., 2007, 126, 447–451.

    Article  CAS  Google Scholar 

  38. D. Frath, S. Azizi, G. Ulrich and R. Ziessel, Org. Lett, 2012, 14, 4774–4777.

    Article  CAS  PubMed  Google Scholar 

  39. X. Ma, J. Cheng, J. Liu, X. Zhou and H. Xiang, New J. Chem., 2014, 39, 492–500.

    Article  CAS  Google Scholar 

  40. D. A. Saffln, K. Robeyns and Y. Garcia, RSC. Adv., 2012, 2, 11379–11388.

    Article  CAS  Google Scholar 

  41. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, 6. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski and D. J. Fox, Gaussian 09, Revision B.0.1, Gaussian, Inc., Wallingford CT, 2009.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Christopher J. Ziegler.

Additional information

Electronic supplementary information (ESI) available: Spectroscopic, and crystallographic data for compounds. CCDC 1523987-1523991 for 1-5. For ESI and crystallographic data in CIF. or other electronic format see DOI: 10.1039/C6pp00479b

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Crandall, L.A., Dawadi, M.B., Burrell, T. et al. Structure and electronics in dimeric boron π expanded azine and salphen complexes. Photochem Photobiol Sci 16, 627–632 (2017). https://doi.org/10.1039/c6pp00479b

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1039/c6pp00479b

Navigation