Skip to main content
Log in

Method of preparation of alkylated 1,3-diphenylpropan-2-ones, the components for assembly of graphene nanostructures

  • Brief Communication
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

Long-chain alkylated 1,3-diphenyl-2-propanones are used in the synthesis of graphene nanostructures (graphene nanoribbons and quantum dots). A reliable procedure to obtain mono- or dialkylated diphenyl-2-propanones in 26 and 38% yields has been proposed. The method includes the dioxolane protection of the keto group in 1,3-di-(4-bromophenyl)-2-propanone, then a palladium-catalyzed cross-coupling reaction of the obtained dioxolane with one-and-a-half- or four-fold excess of dodecyl magnesium bromide that leads to a predominant formation of mono- or dialkylation products respectively, followed by hydrolysis of dioxolanes at the last stage to form the desired diphenyl-2-propanones.

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

References

  1. A. Narita, X. -Y. Wang, X. Feng, K. Müllen, Chem. Soc. Rev., 2015, 44, 6616.

    Article  CAS  Google Scholar 

  2. P. Rufeux, S. Wang, B. Yang, C. Sánchez-Sanchez, J. Liu, T. Dienel, L. Talirz, P. Shinde, C. A. Pignedoli, D. Passerone, T. Dumslaf, X. Feng, K. Müllen, R. Fasel, Nature, 2016, 531, 489.

    Article  Google Scholar 

  3. J. Gao, F. J. Uribe-Romo, J. D. Saathof, H. Arslan, C. R. Crick, S. J. Hein, B. Itin, P. Clancy, W. R. Dichtel, Y.-L. Loo, ACS Nano, 2016, 10, 4847.

    Article  CAS  Google Scholar 

  4. R. S. Jordan, Y. Wang, R. D. McCurdy, M. T. Yeung, K. L. Marsh, S. I. Khan, R. B. Kaner, Y. Rubin, Chem., 2016, 1, 78.

    Article  CAS  Google Scholar 

  5. L. Talirz, P. Rufeux, R. Fasel, Adv. Mater., 2016, 28, 6222.

    Article  CAS  Google Scholar 

  6. H. Sakaguchi, S. Song, T. Kojima, T. Nakae, Nat. Chem., 2017, 9, 57.

    Article  CAS  Google Scholar 

  7. M. Slota, A. Keerthi, W. K. Myers, E. Tretyakov, M. Baumgarten, A. Ardavan, H. Sadeghi, C. J. Lambert, A. Narita, K. Müllen, L. Bogani, Nature, 2018, 557, 691.

    Article  CAS  Google Scholar 

  8. F. Luis, E. Coronado, Nature, 2018, 557, 645.

    Article  CAS  Google Scholar 

  9. A. M. Ziatdinov, N. S. Saenko, P. G. Skrylnik, Russ. Chem. Bull., 2017, 66, 837.

    Article  CAS  Google Scholar 

  10. A. Narita, X. Feng, Y. Hernandez, S. A. Jensen, M. Bonn, H. Yang, I. A. Verzhbitskiy, C. Casiraghi, M. R. Hansen, A. H. R. Koch, G. Fytas, O. Ivasenko, B. Li, K. S. Mali, T. Balandina, S. Mahesh, S. De Feyter, K. Müllen, Nat. Chem., 2014, 6, 126.

    Article  CAS  Google Scholar 

  11. A. Narita, Z. Chen, Q. Chena, K. Müllen, Chem. Sci., 2019, 10, 964.

    Article  CAS  Google Scholar 

  12. X.-Ye Wang, X. Yao, K. Müllen, Sci. China Chem., 2019, 62; DOI: 10.1007/s11426-019-9491-2.

  13. I. C. -Yi Hou, Y. Hul, A. Narita, K. Müllen, Polymer J., 2018, 50, 3.

    Article  Google Scholar 

  14. Yu. Hu, P. Xie, M. De Corato, A. Ruini, S. Zhao, F. Meggendorfer, L. A. Straasø, L. Rondin, P. Simon, J. Li, J. J. Finley, M. R. Hansen, J.-S. Lauret, E. Molinari, X. Feng, J. V. Barth, C.-A. Palma, D. Prezzi, K. Müllen, A. Narita, J. Am. Chem. Soc., 2018, 140, 7803.

    Article  CAS  Google Scholar 

  15. A. Keerthi, B. Radha, D. Rizzo, H. Lu, V. D. Cabanes, I. C.-Y. Hou, D. Beljonne, J. Cornil, C. Casiraghi, M. Baumgarten, K. Mü llen, A. Narita, J. Am. Chem. Soc., 2017, 139, 16454.

    Article  CAS  Google Scholar 

  16. R. Konnerth, C. Cervetti, A. Narita, X. Feng, K. Müllen, A. Hoyer, M. Burghard, K. Kern, M. Dressela, L. Bogani, Nanoscale, 2015, 7, 12807.

    Article  CAS  Google Scholar 

  17. V. Morozov, E. Tretyakov, J. Mol. Model., 2019, 25, 58.

    Article  Google Scholar 

  18. D. Stass, E. Tretyakov, Magnetochemistry, 2019, 5, 32.

    Article  CAS  Google Scholar 

  19. Q. Cao, J. L. Howard, E. Wheatley, D. L. Browne, Angew. Chem., Int. Ed., 2018, 57, 11339.

    Article  CAS  Google Scholar 

  20. Organozinc Reagents in Organic Synthesis, Ed. E. Erdik, CRC Press, New York, 1996.

  21. M. L. Keshtov, E. I. Mal’tsev, D. V. Marochkin, A. V. Muranov, A. R. Khokhlov, Polymer Sci., 2012, 54, 289.

    CAS  Google Scholar 

  22. S. K. Albert, I. Sivakumar, M. Golla, H. Veera, P. Thelu, N. Krishnan, J. Libin, K. L. Ashish, R. Varghese, J. Am. Chem. Soc., 2017, 139, 17799.

    Article  CAS  Google Scholar 

  23. W. D. Neudorf, N. Schulte, D. Lentz, A. D. Schlulter, Org. Lett., 2001, 3, 3115.

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to E. V Tretyakov.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 0172–0175, January, 2020.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Ten, Y.A., Troshkova, N.M. & Tretyakov, E.V. Method of preparation of alkylated 1,3-diphenylpropan-2-ones, the components for assembly of graphene nanostructures. Russ Chem Bull 69, 172–175 (2020). https://doi.org/10.1007/s11172-020-2740-8

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-020-2740-8

Key words

Navigation