Skip to main content
SpringerLink
Log in

Synthesis, X-ray crystal structure, and optical properties of novel 9,9-diethyl-1,2-diaryl-1,9-dihydrofluoreno[2,3-d]imidazoles

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

Abstract

A series of 9,9-diethyl-1,2-diaryl-1,9-dihydrofluoreno[2,3-d]imidazole derivatives were conveniently synthesized by condensation of the key intermediate N 2-aryl-9,9-diethyl-9H-fluorene-2,3-diamine with aldehydes under very mild conditions with good yields. The entire target compounds were characterized using 1H NMR spectroscopy, 13C NMR spectroscopy, high resolution MS, optical absorption, and emission spectra. The crystal structure of 2-(4-bromophenyl)-9,9-diethyl-1-phenyl-1,9-dihydrofluoreno[2,3-d]imidazole was determined as monoclinic, space group P2 1 /c type, using single X-ray crystallography. Most compounds possess medium fluorescence-emitting ability with Φ FL values in the region of 0.40–0.84 and displayed different emission within 379–425 nm in CH2Cl2 depending on the nature of the whole molecule.

Graphical abstract

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

Fig. 1
Fig. 2
Fig. 3

Similar content being viewed by others

References

  1. Tao YT, Yang CL, Qin JG (2011) Chem Soc Rev 40:2943

    Article  CAS  Google Scholar 

  2. Zhu MR, Yang CL (2013) Chem Soc Rev 42:4963

    Article  CAS  Google Scholar 

  3. Tang CW, Van Slyke SA (1987) Appl Phys Lett 51:913

    Article  CAS  Google Scholar 

  4. Baldo MA, O’Brien DF, You Y, Shoustikov A, Sibley S, Thompson ME, Forrest SR (1998) Nature 395:151

    Article  CAS  Google Scholar 

  5. Adachi C, Baldo MA, Forrest SR, Thompson ME (2000) Appl Phys Lett 77:904

    Article  CAS  Google Scholar 

  6. Daghigh LR, Pordel M, Davoodnia A (2014) J Chem Res 4:202

    Article  Google Scholar 

  7. McDonald SM, Mellerup SK, Peng JB, Yang DT, Li QS, Wang S (2015) Chem Eur J 21:13961

    Article  CAS  Google Scholar 

  8. Khan SA, Asiri AM, Basisi HM (2015) J Fluoresc 25:825

    Article  CAS  Google Scholar 

  9. Baldo MA, Lamansky S, Burrows PE, Thompson ME, Forrest SR (1999) Appl Phys Lett 75:4

    Article  CAS  Google Scholar 

  10. Lamansky S, Djurovich P, Murphy D, Abdel-Razzaq F, Lee HE, Adachi C, Burrows PE, Forrest SR, Thompson ME (2001) J Am Chem Soc 123:4304

    Article  CAS  Google Scholar 

  11. Luzio A, Fazzi D, Natali D (2014) Adv Funct Mater 24:1151

    Article  CAS  Google Scholar 

  12. Shin J, Hong TR, Lee TW (2014) Adv Mater 26:6031

    Article  CAS  Google Scholar 

  13. Shanmugasundaram K, Subeesh MS, Sunesh CD, Chitumalla RK, Jang J, Choe Y (2015) Org Electron 24:297

    Article  CAS  Google Scholar 

  14. Irfan M, Belfield KD, Saeed A (2015) RSC Adv 5:48760

    Article  CAS  Google Scholar 

  15. Brunner K, van Dijken A, Borner H (2004) J Am Chem Soc 126:6035

    Article  CAS  Google Scholar 

  16. Qian JC, Jia KP, Yu JS (2010) Spectrosc Spect Anal 30:625

    CAS  Google Scholar 

  17. Namchul C, Byoung KC, Hwansoo S (2010) J Nanosci Nanotechnol 10:6925

    Article  Google Scholar 

  18. Qian YB, Cao F, Guo WP (2013) Tetrahedron 69:4169

    Article  CAS  Google Scholar 

  19. Thiery S, Tondelier D, Declairieux C (2014) J Mater Chem C 2:4156

    Article  CAS  Google Scholar 

  20. Cocherel N, Poriel C, Berthelot JR, Barrière F, Slawin AMA, Vignau L (2008) Chem Eur J 14:328

    Article  Google Scholar 

  21. Sun B, Liu K, Han J (2015) Bioorg Med Chem 23:6763

    Article  CAS  Google Scholar 

  22. Li Q, Hu QH, Wang XN (2015) Chem Biol Drug Des 86:509

    Article  CAS  Google Scholar 

  23. Fei WW, Hu GJ, Li R (2013) Mater Chem Phys 139:403

    Article  CAS  Google Scholar 

  24. Wang ZM, Ma LL, Zhang XJ (2013) Adv Mater Res 710:17

    Article  CAS  Google Scholar 

  25. Cocherel N, Poriel C, Berthelot JR, Barrière F, Slawin AMA, Vignau L (2008) Chem Eur J 14:11328

    Article  CAS  Google Scholar 

  26. Wong KT, Chao TC, Chi LC, Chu YY, Balaiah A, Chiu SF (2006) Org Lett 8:5033

    Article  CAS  Google Scholar 

  27. Du CY, Ye SH, Chen JM, Guo YL, Liu YQ, Lu K (2009) Chem Eur J 15:8275

    Article  CAS  Google Scholar 

  28. Hao ZS, Li MJ, Lin HX, Gu ZB, Cui YM (2014) Dyes Pigm 109:54

    Article  CAS  Google Scholar 

  29. Guo JG, Cui YM, Lin HX, Xie XZ, Chen HF (2011) J Photochem Photobiol, A 219:42

    Article  CAS  Google Scholar 

  30. Chen HF, Cui YM, Guo JG, Lin HX (2012) Dyes Pigm 94:583

    Article  CAS  Google Scholar 

  31. Guo X, Rao HH, Fu H, Jiang YY, Zhao YF (2006) Adv Synth Catal 348:2197

    Article  CAS  Google Scholar 

  32. Beaulieu PL, Haché B, Moos EV (2003) Synthesis 11:1683

    Article  Google Scholar 

Download references

Acknowledgments

The authors are grateful for supports from the National Natural Science Foundation of China (Project No. 81202402 and 21272154). The authors also thank Drs. H. Deng and M. Shao, The Instrumental Analysis & Research Center of Shanghai University, for structural analysis.

Author information

Authors and Affiliations

  1. Department of Chemistry, College of Sciences, Shanghai University, Shanghai, 200444, People’s Republic of China

    Tian-Qi Wang, Shao-Liang Zhao, Wen-Ming Zhang, Hai-Xia Lin & Yong-Mei Cui

Authors
  1. Tian-Qi Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Shao-Liang Zhao
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Wen-Ming Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Hai-Xia Lin
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Yong-Mei Cui
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Hai-Xia Lin or Yong-Mei Cui.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOC 76 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Wang, TQ., Zhao, SL., Zhang, WM. et al. Synthesis, X-ray crystal structure, and optical properties of novel 9,9-diethyl-1,2-diaryl-1,9-dihydrofluoreno[2,3-d]imidazoles. Monatsh Chem 147, 1991–1999 (2016). https://doi.org/10.1007/s00706-016-1716-8

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-016-1716-8

Keywords

Search

Navigation