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Journal of Fluorescence

, Volume 20, Issue 5, pp 1037–1047 | Cite as

Synthesis, Electrochemical, and Optical Properties of New Fluorescent, Substituted Thieno[3,2-b][1]Benzothiophenes

  • Cheikh Lô
  • Jean-Jacques AaronEmail author
  • Václav Kozmík
  • Jiří Svoboda
  • Jean-Claude Brochon
  • Li Na
Original Paper

Abstract

The synthesis, electrochemical and optical properties of three fluorescent substituted thieno[3,2-b][1]benzothiophenes (TBT) derivatives, including 3-methoxythieno[3,2-b][1]benzothiophene (3-MeO-TBT), 2,3-dimethylthieno[3,2-b][1]benzothiophene (2,3-diMe-TBT), and 6-methoxythieno[3,2-b][1]benzothiophene-2-carboxylate (6-MeO-TBT-2-COOMe), were investigated. The oxidation potential values varied between 1.40 and 1.20 V/SCE according to the electronic substituent effect, and electropolymerization attempts, performed in 0.1 M LiClO4 acetonitrile solution, led to the formation of very thin films of poly(3-MeO-TBT) and poly(2,3-di-Me-TBT). Electronic absorption spectra, fluorescence excitation and emission spectra, fluorescence quantum yields (ΦF) , lifetimes (τF), and other photophysical parameters of the three new TBT derivatives were measured in DMSO solutions at room temperature. For the methyl-and methoxy-substituted TBT derivatives, the fluorescence emission peak were slightly red shifted relative to that of unsubstituted TBT (Δλem = 1–12 nm) whereas, in the case of 6-MeO-TBT-2-COOMe, a rather strong red-shift (Δλem = 73 nm) was attributed to the existence of a “push-pull” electronic interaction of the MeO and COOMe groups. All ΦF values were rather high, varying between 0.11 and 0.35, according to the substituent effect. Fluorescence decays were mono-exponential and τF values were very short, ranging between 0.11 and 0.30 ns for the substituted TBT derivatives until study.

Keywords

Synthesis TBT substituted derivatives Fluorescent compounds Optical properties Electrochemical properties 

Notes

Acknowledgements

This work was, in part, financially supported by the Ministry of Education, Youth and Sports of the Czech Republic (projects MSM 6046137301 and OC176) and by the French Ministry of Foreign Affairs (French-Czech research project Barrande N°03079SF). Dr. C. Lô gratefully thanks the Senegalese Ministry of Education for a Ph.D. grant. Dr. Li Na warmly thanks the ENS of Cachan for a Ph.D. grant.

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Copyright information

© Springer Science+Business Media, LLC 2010

Authors and Affiliations

  • Cheikh Lô
    • 1
    • 6
  • Jean-Jacques Aaron
    • 1
    • 2
    Email author
  • Václav Kozmík
    • 3
  • Jiří Svoboda
    • 3
  • Jean-Claude Brochon
    • 4
  • Li Na
    • 4
    • 5
  1. 1.Laboratoire ITODYS, associé au CNRS UMR 7086Université Paris DiderotParis Cedex 13France
  2. 2.Laboratoire LGEUniversité Paris-Est-Marne-la-ValléeMarne-la-Vallée Cedex 2France
  3. 3.Department of Organic ChemistryPrague Institute of TechnologyPRAGUE 6Czech Republic
  4. 4.LBPA-CNRS UMR 8113, ENS de CachanCachanFrance
  5. 5.Department of Life ScienceEast China Normal UniversityShanghaiChina
  6. 6.Département de Chimie, Faculté des Sciences et TechniquesUniversité Cheikh Anta DiopDakarSénégal

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