Journal of Fluorescence

, Volume 23, Issue 3, pp 425–437 | Cite as

N-Triazinyl Derivatives of 1- and 9-aminoanthracene: Synthesis and Photo-Physical Properties

  • Hana Přichystalová
  • Numan Almonasy
  • Miloš Nepraš
  • Filip Bureš
  • Miroslav Dvořák
  • Martin Michl
  • Jiři Čermák
  • Ladislav Burgert
ORIGINAL PAPER

Abstract

New N-triazinyl derivatives were synthesized by reaction of cyanuric chloride with 1- and 9-aminoanthracenes and subsequent nucleophilic substitution of chlorine atoms on triazinyl ring with methoxy and/or phenylamino groups. The compounds were characterized by 1H and 13C NMR and mass spectra. The influence of the chemical structure and solvent polarity on the UV/Vis absorption and fluorescence spectra and fluorescence quantum yields were investigated. Semi-empirical computations revealed highly polar CT states in singlet excited state manifold connected with charge-transfer from the hydrocarbon moiety to the triazinyl ring. The relationships between the CT-to-emitting state energy gap, solvent polarity and fluorescence quantum yield were discussed.

Keywords

N-Triazinyl aminoanthracenes Synthesis Fluorescence spectra Quantum yield Quenching 

References

  1. 1.
    Förster T (1965) In: Sinanoglu O (ed) Modern quantum chemistry, istanbul lectures, Part III. Academic, New York, pp 93–137Google Scholar
  2. 2.
    El-Sayed MA (1995) In: Molin TIY (ed) Ultrafast processes in chemistry and photobiology, a chemistry for 21st century monograph. IUPAC and Blackwell Science Ltd, UKGoogle Scholar
  3. 3.
    Khoo I-C, Simoni F, Umeton C (1997) Novel optical materials and applications. Wiley, New YorkGoogle Scholar
  4. 4.
    Fidler V et al (2002) Femtosecond fluorescence anisotropy kinetics as a signature of ultrafast electronic energy transfer in bichromophoric molecules. Z Phys Chem 216:589–603CrossRefGoogle Scholar
  5. 5.
    Almonasy N et al (2009) Synthesis of bi- and trichromophoric dyes bearing ans-triazinyl ring spacer. Dyes Pigments 82:416–421CrossRefGoogle Scholar
  6. 6.
    Kapusta P et al (2003) Photophysics of 3-substituted benzanthrones: substituent and solvent control of intersystem crossing. J Phys Chem A 107:9740–9746CrossRefGoogle Scholar
  7. 7.
    Šoustek P et al (2008) The synthesis and fluorescence of N-substituted 1- and 2- aminopyrenes. Dyes Pigments 78(2):139–147CrossRefGoogle Scholar
  8. 8.
    Almonasy N et al (2009) The synthesis of N-derivatives of 3-aminoperylene and their absorption and fluorescence properties. Dyes Pigments 82(2):164–170CrossRefGoogle Scholar
  9. 9.
    El-Sedik et al (2012) Synthesis, absorption and fluorescence properties of N-triazinyl derivatives of 2-aminoanthracene. Dyes Pigments 92(3):1126–1131CrossRefGoogle Scholar
  10. 10.
    Nepraš M et al (2012) Electronic structure, spectra and photophysical properties ofN-triazinylderivatives of1-aminopyrene. Semiempirical theoretical study. Dyes Pigments 92(3):1331–1336CrossRefGoogle Scholar
  11. 11.
    Hirano K et al (2009) A modular synthesis of highly substituted imidazolium salts. Org Lett 11(4):1019–1022PubMedCrossRefGoogle Scholar
  12. 12.
    Rigaudy J et al (1981) Studies of meso-aminoanthracenes. VIII. Methyl 10-amino-9-anthracenecarboxylate. Oxidation and diazotization. Bull Soc Chim Fr 5–6(2):223–230Google Scholar
  13. 13.
    Verma SM, Singh MD (1977) Structural elucidation with nuclear magnetic resonance spectroscopy. Diels-Alder adducts of 1-aminoanthracene and maleic anhydride: restricted rotation about the aryl C(1)-N bond and intrinsic asymmetry about the imide (Nsp2-Csp3) system. J Org Chem 42(23):3736–3740CrossRefGoogle Scholar
  14. 14.
    Birks JB et al (1963) The relations between the fluorescence and absorption properties of organic molecules. Proc R Soc A 275:135–148CrossRefGoogle Scholar
  15. 15.
    Bures F et al (2006) Novel nitrogen ligands based on imidazole derivatives and their application in asymmetric catalysis. Tetrahedron: Asymmetry 17(6):900–907CrossRefGoogle Scholar
  16. 16.
    Thompson MA (2009) ArgusLab 4.0, Planaria Software LLC, Seattle, WA, http://www.arguslab.com. 29

Copyright information

© Springer Science+Business Media New York 2013

Authors and Affiliations

  • Hana Přichystalová
    • 1
  • Numan Almonasy
    • 1
  • Miloš Nepraš
    • 1
  • Filip Bureš
    • 1
  • Miroslav Dvořák
    • 2
  • Martin Michl
    • 2
  • Jiři Čermák
    • 3
  • Ladislav Burgert
    • 1
  1. 1.Institute of Organic Chemistry and Technology and Institute of Polymeric Materials, Faculty of Chemical TechnologyUniversity of PardubicePardubiceCzech Republic
  2. 2.Department of Physical Electronics, Faculty of Nuclear Sciences and Physical EngineeringCzech Technical University in PraguePragueCzech Republic
  3. 3.Research Institute for Organic SynthesesPardubiceCzech Republic

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