Skip to main content
Log in

Synthesis of 2,2′-diamino-7-tert-butyl-9,9′-spirobifluorene starting from 4,4′-di-tert-butylbiphenyl

  • Original Paper
  • Published:
Monatshefte für Chemie - Chemical Monthly Aims and scope Submit manuscript

Abstract

A novel spirobifluorene diamine monomer, 2,2′-diamino-7-tert-butyl-9,9′-spirobifluorene, was obtained starting from the readily available reagent 4,4′-di-tert-butylbiphenyl. The key step of the synthesis is the introduction of a nitro group into the 2-position of the spirobifluorene through the loss of tert-butyl at the 2-position.

Graphical Abstract

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.

Scheme 1

Similar content being viewed by others

References

  1. Park D-J, Noh Y-Y, Kim J-J, Kim D-Y (2002) Polym Prepr 43:71

    CAS  Google Scholar 

  2. Wong K-T, Ku S-Y, Cheng Y-M, Lin X-Y, Hung Y-Y, Pu S-C, Chou P-T, Lee G-H, Peng S-M (2006) J Org Chem 71:456

    Article  CAS  Google Scholar 

  3. Cheng X, Hou G-H, Xie J-H, Zhou Q-L (2004) Org Lett 6:2381

    Article  CAS  Google Scholar 

  4. Thiemann F, Piehler T, Haase D, Saak W, Lützen A (2005) Eur J Org Chem 10:1991

    Article  Google Scholar 

  5. Yang GC, Su ZM, Qin CS (2006) J Phys Chem A 110:4817

    Article  CAS  Google Scholar 

  6. Xiao HB, Wang L, Tao XM, Chen MJ (2010) Synth Met 160:1313

    Article  CAS  Google Scholar 

  7. Xiao HB, Tao XM, Wang YC, Qian SX, Shi GH, Li H (2008) Tetrahedron Lett 49:6819

    Article  CAS  Google Scholar 

  8. Li M-X, Han K, Li H-P, Ge Y, Wua Q-H, Tang G, Wu Y-X (2010) J Mol Struct (Theochem) 957:31

    Article  CAS  Google Scholar 

  9. Brendel CM, Dias FB, Saragi TPI, Monkman AP, Salbeck J (2009) Phys Status Solidi A 206:2715

    CAS  Google Scholar 

  10. Hoffmann R, Imamura A, Zeiss GD (1967) J Am Chem Soc 89:5215

    Article  CAS  Google Scholar 

  11. Simmons HE, Fukunaga T (1967) J Am Chem Soc 89:5208

    Article  CAS  Google Scholar 

  12. Bucknum MJ, Hoffmann R (1994) J Am Chem Soc 116:11456

    Article  CAS  Google Scholar 

  13. Saragi TPI, Spehr T, Siebert A, Fuhrmann-Lieker T, Salbeck J (2007) Chem Rev 107:1011

    Article  CAS  Google Scholar 

  14. Clarkson RG, Gomberg DM (1930) J Am Chem Soc 52:2881

    Article  CAS  Google Scholar 

  15. Wu F-I, Dodda R, Reddy DS, Shu C-F (2002) J Mater Chem 12:2893

    Article  CAS  Google Scholar 

  16. Chou CH, Reddy DS, Shu CF (2002) J Polym Sci Part A Polym Chem 40:3615

    Article  CAS  Google Scholar 

  17. Bach U, Cloedt KD, Spreitzer H, Grätzel M (2000) Adv Mater 12:1060

    Article  CAS  Google Scholar 

  18. Suzuki H, Takeuchi T, Mori T (1996) J Org Chem 61:5944

    Article  CAS  Google Scholar 

  19. Tashiro M, Yamato T (1979) J Org Chem 44:3037

    Article  CAS  Google Scholar 

  20. Kim Y-H, Kim H-S, Kwon S-K (2005) Macromolecules 38:7950

    Article  CAS  Google Scholar 

  21. Wong KT, Liao YL, Peng YC, Wang CC, Lin SY, Yang CH, Tseng SM, Lee GH, Peng SM (2005) Cryst Growth Des 5:667

    Article  CAS  Google Scholar 

  22. Ramesh C, Kavala V, Kuo C-W, Yao C-F (2010) Tetrahedron Lett 51:5234

    Article  CAS  Google Scholar 

  23. Jiang G-M, Jiang X, Zhu Y-F, Huang D, Jing X-H, Gao W-D (2010) Polym Int 59:896

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work was financially supported by the Innovation Program of Shanghai Municipal Education Commission (no. 09YZ160) and the Natural Science Foundation of Shanghai City of China (no. 11ZR1426200).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Haibo Xiao.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Xiao, H., Yin, H., Wang, L. et al. Synthesis of 2,2′-diamino-7-tert-butyl-9,9′-spirobifluorene starting from 4,4′-di-tert-butylbiphenyl. Monatsh Chem 143, 683–686 (2012). https://doi.org/10.1007/s00706-011-0620-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-011-0620-5

Keywords

Navigation