Journal of Fluorescence

, Volume 26, Issue 4, pp 1457–1466 | Cite as

Synthesis and Optoelectronic Properties of Thiophene Donor and Thiazole Acceptor Based Blue Fluorescent Conjugated Oligomers



We report on the synthesis and characterization of low band gap, blue light emitting and thermal stable conjugated oligomer by Wittig condensation. Thiophene and thiazole type of donor-acceptor based series of conjugated oligomers, Oligo-4,5-bis-[2-[5-[2-thiophene-2-yl-vinyl]thiophene-2-yl]-vinyl]-thiazole (OBTV-TZ) and Oligo-2,4,5-Tris–[2-[5-[2-thiophene-2-yl-vinyl]thiophene-2-yl]-vinyl]-thiazole (OTTV-TZ) were synthesized. These oligomers were confirmed by FT-IR and 1H-NMR and LC/MS analysis. The effect of the number of thiophene rings on the optical, electrochemical, thermal and morphological properties of the oligomers were systematically investigated. Both oligomers were exhibited almost same absorption wavelength in methanol solution (λmax = 365 nm and 369 nm) which indicates both oligomers illustrate similar intra molecular charge transfer (ICT). In solid state, the oligomers were exhibited broadening peaks with higher onset absorptions (λmax = 600 nm and 580 nm). The photoluminescence absorption spectrum of the oligomers was observed at 433 nm and 434 nm respectively in methanol solution with blue emission. The electrochemical band gap (\( {E}_g^{ec} \)) of the OBTV-TZ was 1.55 eV (low band gap) and OTTV-TZ was exhibited greater highest occupied molecular orbital (HOMO) value (E HOMO = −6.6 eV). Moreover morphological parameters of both oligomer film of 2D and 3D diagrams were observed by using AFM studies.


Blue light emitting Conjugated oligomers Thiophene Thiazole Internal charge transfer Low band gap 



This work was financially supported by DST-SERB, New Delhi (Grant no. SB/FT/CS-140/2013). The authors are grateful to DST/VIT-FIST, VIT University for providing instrumental facilities.


  1. 1.
    Bredas JL, Beljonne D, Coropceanu V, Cornil J (2004) Chem Rev 104:4971CrossRefPubMedGoogle Scholar
  2. 2.
    Won YS, Yang YS, Kim JH, Ryu JH, Kim KK, Park SS (2010) Energy Fuel 24:3676CrossRefGoogle Scholar
  3. 3.
    Promarak V, Punkvuang A, Sudyoadsuk T, Jungsuttiwong S, Saengsuwan S, Keawin T, Sirithip K (2007) Tetrahedron 63:8881CrossRefGoogle Scholar
  4. 4.
    Garnier F (1998) Chem Phys 227:253CrossRefGoogle Scholar
  5. 5.
    Oleksy AN, Cabaj J, Olech K, Soloducho J, Roszak S (2011) J Fluoresc 21:1625CrossRefGoogle Scholar
  6. 6.
    Zheng S, Shi J (2001) Chem Mater 13:4405CrossRefGoogle Scholar
  7. 7.
    Anderson S, Taylor PN, Verschoor GLB (2004) Chem Eur J 10:518CrossRefPubMedGoogle Scholar
  8. 8.
    Hou J, Yang C, Qiao J, Li Y (2005) Synt Met 150:297Google Scholar
  9. 9.
    Jin SH, Kim MY, Kim JY, Lee K, Gal YS (2004) J Am Chem Soc 126:2474CrossRefPubMedGoogle Scholar
  10. 10.
    Hosokawa C, Higashi H, Nakamura H, Kusumoto T (1995) Appl Phys Lett 67:3853CrossRefGoogle Scholar
  11. 11.
    Jacob J, Sax S, Piok T, List EJW, Grimsdale AC, Mullen K (2004) J Am Chem Soc 126:6987CrossRefPubMedGoogle Scholar
  12. 12.
    Pei J, Wen S, Zhou Y, Dong Q, Liu Z, Zhang J, Tian W (2011) New J Chem 35:385CrossRefGoogle Scholar
  13. 13.
    Bundgaard E, Krebs FC (2007) Sol Energy Mater Sol Cells 91:954CrossRefGoogle Scholar
  14. 14.
    Hu C, Wu Z, Cao K, Sun B, Zhang Q (2013) Polymer 54:1098CrossRefGoogle Scholar
  15. 15.
    Jo JW, Kim SS, Jo WH (2012) Org Electron 13:1322CrossRefGoogle Scholar
  16. 16.
    Aleman EA, Silva CD, Patrick EM, Forsyth KM, Rueda D (2014) J Phys Chem Lett 5:777CrossRefPubMedPubMedCentralGoogle Scholar
  17. 17.
    Iranfar H, Rajabi O, Salari R, Chamani J (2012) J Phys Chem B 116:1951CrossRefPubMedGoogle Scholar
  18. 18.
    Sattar Z, Saberi MR, Chamani J (2004) PLoS One 9:84045CrossRefGoogle Scholar
  19. 19.
    Sattar Z, Iranfar H, Asoodeh A, Saberi MR, Mazhari M, Chamani J (2012) Spectrochim Acta A 97:1089CrossRefGoogle Scholar
  20. 20.
    Sarzehi S, Chamani J (2010) Int J Biol Macromol 47:558CrossRefPubMedGoogle Scholar
  21. 21.
    Mei J, Heston NC, Vasilyeva SV, Reynolds JR (2009) Macromolecules 42:1482CrossRefGoogle Scholar
  22. 22.
    Huang J, Xu Y, Hou Q, Yang W, Yuan M, Cao Y (2002) Macromol Rapid Commun 23:709CrossRefGoogle Scholar
  23. 23.
    Belavagi NS, Deshapande N, Pujar GH, Wari MN, Inamdar SR, Khazi IAM (2015) J Fluoresc 25:1323CrossRefPubMedGoogle Scholar
  24. 24.
    Byrne PA, Higham LJ, Mc Govern P, Gilheany DG (2013) Tetrahedron Lett 53:6701CrossRefGoogle Scholar
  25. 25.
    Liu D, Sun L, Du Z, Xiao M, Gu C, Wang T, Wen S, Sun M, Yang R (2014) RSC Adv (2014) 4:37934Google Scholar
  26. 26.
    Upadhyay A, Karpagam S (2016) J Fluoresc 26:439CrossRefPubMedGoogle Scholar
  27. 27.
    Sridhar I, Panchamukhi, Belavagi N, Rabinal MH, Khazi IM (2011) J Fluoresc 21:1515Google Scholar
  28. 28.
    Liu T, Chen Z, Yu W, You S (2011) Water Res 45:2111CrossRefPubMedGoogle Scholar
  29. 29.
    Aldissi M (1993) Springer Science And Business Media 128Google Scholar
  30. 30.
    Karpagam S, Guhanathan S, Sakthivel P (2012) Fibers and Polymers 13:1105Google Scholar
  31. 31.
    Upadhyay A, Karpagam S (2015) J Photopolym Sci Technol 28:755CrossRefGoogle Scholar
  32. 32.
    Zhu Y, Champion RD, Jenekhe SA (2006) Macromolecules 39:8712CrossRefGoogle Scholar
  33. 33.
    Wang H, Songa N, Li H, Li Y, Li X (2005) Synth Met 151:279CrossRefGoogle Scholar
  34. 34.
    Gong X, Li G, Li C, Zhang J, Bo Z (2015) J Mater Chem A 3:20195CrossRefGoogle Scholar
  35. 35.
    Mikroyannidis JA, Tsagkournos DV, Balraj P, Sharma GD (2011) Sol Energy Mater Sol Cells 95:3025CrossRefGoogle Scholar
  36. 36.
    Hoven C, Dang XD, Coffin RC, Peet J, Nguyen TQ, Bazan GC (2010) Adv Mater 22:E63CrossRefPubMedGoogle Scholar
  37. 37.
    Krebs FC, Gevorgyan SA, Alstrup J (2009) J Mater Chem 19:5442CrossRefGoogle Scholar
  38. 38.
    Jin BM, Lee SH, Zong K, Lee YS (2010) Synth Met 160:1197CrossRefGoogle Scholar
  39. 39.
    Dutta P, Yang W, Park H, Baek MJ, Lee YS, Lee SH (2011) Synth Met 161:1582CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2016

Authors and Affiliations

  1. 1.Organic Chemistry Division, School of Advanced SciencesVIT UniversityTamil NaduIndia

Personalised recommendations