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.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Förster T (1965) In: Sinanoglu O (ed) Modern quantum chemistry, istanbul lectures, Part III. Academic, New York, pp 93–137
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, UK
Khoo I-C, Simoni F, Umeton C (1997) Novel optical materials and applications. Wiley, New York
Fidler V et al (2002) Femtosecond fluorescence anisotropy kinetics as a signature of ultrafast electronic energy transfer in bichromophoric molecules. Z Phys Chem 216:589–603
Almonasy N et al (2009) Synthesis of bi- and trichromophoric dyes bearing ans-triazinyl ring spacer. Dyes Pigments 82:416–421
Kapusta P et al (2003) Photophysics of 3-substituted benzanthrones: substituent and solvent control of intersystem crossing. J Phys Chem A 107:9740–9746
Šoustek P et al (2008) The synthesis and fluorescence of N-substituted 1- and 2- aminopyrenes. Dyes Pigments 78(2):139–147
Almonasy N et al (2009) The synthesis of N-derivatives of 3-aminoperylene and their absorption and fluorescence properties. Dyes Pigments 82(2):164–170
El-Sedik et al (2012) Synthesis, absorption and fluorescence properties of N-triazinyl derivatives of 2-aminoanthracene. Dyes Pigments 92(3):1126–1131
Nepraš M et al (2012) Electronic structure, spectra and photophysical properties ofN-triazinylderivatives of1-aminopyrene. Semiempirical theoretical study. Dyes Pigments 92(3):1331–1336
Hirano K et al (2009) A modular synthesis of highly substituted imidazolium salts. Org Lett 11(4):1019–1022
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):223–230
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):3736–3740
Birks JB et al (1963) The relations between the fluorescence and absorption properties of organic molecules. Proc R Soc A 275:135–148
Bures F et al (2006) Novel nitrogen ligands based on imidazole derivatives and their application in asymmetric catalysis. Tetrahedron: Asymmetry 17(6):900–907
Thompson MA (2009) ArgusLab 4.0, Planaria Software LLC, Seattle, WA, http://www.arguslab.com. 29
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Přichystalová, H., Almonasy, N., Nepraš, M. et al. N-Triazinyl Derivatives of 1- and 9-aminoanthracene: Synthesis and Photo-Physical Properties. J Fluoresc 23, 425–437 (2013). https://doi.org/10.1007/s10895-013-1156-3
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10895-013-1156-3