Abstract
Two new 7-N,N-diphenylamino-3-benzoheterocyclic coumarin derivatives containing electron-transporting benzotriazolyl or benzoxazolyl moiety, 3-(1-benzotriazole)-7-N,N-diphenylaminocoumarin (BTDC) and 3-(2-benzoxazole)-7-N,N-diphenylaminocoumarin (BODC), were synthesized and characterized by element analysis, 1H NMR and FT-IR spectra. The UV–vis and fluorescence spectra of these coumarin derivatives were investigated. The results show that BTDC and BODC exhibit strong blue and red emissions, respectively, under ultraviolet light excitation. The relationships between the chemical structure and the fluorescence characteristics of the 7-N,N-diphenylamino-3-benzoheterocyclic coumarin derivatives are discussed. It was found that the coumarin derivative will become a high-efficiency emitting material when an amino group is attached in 7-position of the coumarin ring, and 7- strong electron donors can improve the ability of the intramolecular charge transfer of the coumarin molecules.
Similar content being viewed by others
References
R.P. Haugland, M.T.Z. Spence, I.D. Johnson, Handbook of fluorescent probes and research chemicals, 6th edn. (Molecular Probes, Eugene, 1996)
H. Schwander, P. Hendrix, in Ullmann’s encyclopedia of industrial chemistry, vol. A11, 5th edn., ed. by Y.S. Yamamoto (VCH, Weinheim, 1988), p. 280
O.S. Wolfbeis, E. Koller, P. Hochmuth, Bull. Chem. Soc. Jpn. 58, 731–734 (1985)
U. Tripathy, P.B. Bisht, J. Chem. Phys. 125, 144502–144509 (2006)
S.L. Gilat, A. Adronov, J.M.J. Fréchet, Angew. Chem. Int. Ed. 38, 1422–1427 (1999)
H. Imahori, T. Umeyama, S. Ito, Acc. Chem. Res. 42, 1809–1818 (2009)
S. Franco, J. Garin, N.M. De Baroja, R. Pérez-Tejada, J. Orduna, Y.H. Yu, M. Lira-Cantú, Org. Lett. 14, 752–755 (2012)
S.P. Singh, M.S. Roy, K.R. Justin Thomas, S. Balaiah, K. Bhanuprakash, G.D. Sharma, J. Phys. Chem. C 116, 5941–5950 (2012)
G.S. Jiao, L.H. Thoresen, K. Burgess, J. Am. Chem. Soc. 125, 14668–14669 (2003)
K. Staub, G.A. Levina, S. Barlow, T.C. Kowalczyk, H.S. Lackritz, M. Barzoukas, A. Fortd, S.R. Marder, J. Mater. Chem. 13, 825–833 (2003)
T.Z. Yu, P. Zhang, Y.L. Zhao, H. Zhang, J. Meng, D.W. Fan, L.L. Chen, Y.Q. Qiu, Org. Electron. 11, 41–49 (2010)
Z.J. Ning, Q. Zhang, W.J. Wu, H.C. Pei, B. Liu, H. Tian, J. Org. Chem. 73, 3791–3797 (2008)
Q. Xu, H.Z. Chen, M. Wang, J. Funct. Mater. 36, 1659–1663 (2005)
Y. Imai, M. Ishida, M.A. Kakimoto, High Perform. Polym. 15, 281–290 (2003)
C. Lambent, G. Noll, Synth. Met. 139, 57–62 (2003)
S.A. Swanson, G.M. Wallraff, J.P. Chen, W.J. Zhang, L.D. Bozano, K.R. Carter, J.R. Salem, R. Villa, J.C. Scott, Chem. Mater. 15, 2305–2312 (2003)
Y.L. Zhao, T.Z. Yu, Y.Z. Wu, H. Zhang, D.W. Fan, Z.W. Gan, L.L. Yang, X.Q. Han, Y.M. Zhang, J. Fluoresc. 22, 631–638 (2012)
C.T. Chen, C.L. Chiang, Y.C. Lin, L.H. Chan, C.H. Huang, Z.W. Tsai, C.T. Chen, Org. Lett. 5, 1261–1264 (2003)
M. Kaholek, P. Hrdlovič, J. Photochem. Photobiol. A Chem. 127, 45–55 (1999)
Acknowledgments
This work was financially supported by the National Natural Science Foundation of China (Grant 61166003) and the Natural Science Foundation of Gansu Province (1010RJZA060), and also supported by the Program for Changjiang Scholars and Innovative Research Team in University (IRT0629).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Yu, T., Zhao, M., Li, A. et al. Synthesis and photoluminescent properties of 7-N,N-diphenylamino-3- benzoheterocyclic coumarin derivatives. Res Chem Intermed 39, 2259–2266 (2013). https://doi.org/10.1007/s11164-012-0755-y
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11164-012-0755-y