In this work, a new ligand (13)aneN4 with anthracene was synthesized and characterized by mass spectrometry, NMR, UV-Vis and fluorescence spectroscopies. The ligand has a double fluorescence explained by the presence of a photoinduced charge transfer. The fluorescence spectra in various solvents show an increase in the intensity of the band charge transfer with solvent polarity and a decrease in the intensity of the band of the locally excited state of anthracene. The fluorescence studies was also performed in order to study the influence of pH on the charge transfer band, therefore, the ligand can be considered as “pH sensor” in the pH range (10 - 11). Finally, we show that the dual fluorescence intensity of the complex L-metal could be influenced by the coordination of the exocyclic nitrogen atom to the central metal.
Cite this paper
Jabri, R. Z. , Lemeune, A. , Zrineh, A. and Denat, F. (2023). Study of the Double Fluorescence of a New Anthracene (13)aneN4. Open Access Library Journal, 10, e474. doi: http://dx.doi.org/10.4236/oalib.1110474.
Meyer, M., Dahaoui-Gindrey, V., Lecomte, C. and Guilard, R. (1998) Conformations and Coordination Schemes of Carboxylate and Carbamoyl Derivatives of the Tetraazamacrocycles Cyclen and Cyclam, and the Relation to Their Protonation States. Coordination Chemistry Reviews, 178-180, 1313-1405.
Shokeen, M. and Anderson, C.J. (2009) Molecular Imaging of Cancer with Copper-64 Radiopharmaceuticals and Positron Emission Tomography (PET). Accounts of Chemical Research, 42, 832-841. https://doi.org/10.1021/ar800255q
Cai, Z. and Anderson, C.J. (2014) Chelators for Copper Radionuclides in Positron Emission Tomography Radiopharmaceuticals. Journal of Labelled Compounds and Radiopharmaceuticals, 57, 224-230. https://doi.org/10.1002/jlcr.3165
Zhang, H., Kang, D., Huang, B., Liu, N., Zhao, F., Zhan, P. and Liu, X. (2016) Discovery of Non-Peptide Small Molecular CXCR4 Antagonists as Anti-HIV Agents: Recent Advances and Future Opportunities. European Journal of Medicinal Chemistry, 114, 65-78. https://doi.org/10.1016/j.ejmech.2016.02.051
Guilard, R., Chollet, H., Guiberteau, P. and Cocolios, P. (1996) Material Comprising Polyazacycloalkanes Grafted onto Polypropylene Fibres Method for Production thereof and Method for Removal of Metal Cations from a Liquid.
Machitani, K., Nakahara, Y. and Kimura, K. (2009) Photochemical Modulation of Europium Ion Fluorescence Using a Tetraazamacrocyclic Derivative Bearing a Spirobenzopyran and Three Carboxymethyl Moieties. Bulletin of the Chemical Society of Japan, 82, 472-474. https://doi.org/10.1246/bcsj.82.472
Esmieu, C., Guettas, D., Conte-Daban, A., Sabater, L., Faller, P. and Hureau, C. (2019) Copper-Targeting Approaches in Alzheimer’s Disease: How to Improve the Fallouts Obtained from in vitro Studies. Inorganic Chemistry, 58, 13509-13527.
Blair, S., Lowe, M.P., Mathieu, C.E., Parker, D., Senanayake, P.K. and Kataky, R. (2001) Narrow-Range Optical pH Sensors Based on Luminescent Europium and Terbium Complexes Immobilized in a Sol Gel Glass. Inorganic Chemistry, 40, 5860-5867. https://doi.org/10.1021/ic010371w
Parker, D., Senanayake, K. and Williams, J.A.G. (1997) Luminescent Chemosensors for pH, Halide and Hydroxide Ions Based on Kinetically Stable, Macrocyclic Europium-Phenanthridinium Conjugates. Chemical Communications, No. 18, 1777-1778. https://doi.org/10.1039/a704318j
Parker, D. and Williams, J.A.G. (1998) Taking Advantage of the pH and pO2 Sensitivity of a Luminescent Macrocyclic Terbium Phenanthridyl Complex. Chemical Communications, No. 2, 245-246. https://doi.org/10.1039/a707754h
Parker, D., Senanayake, P.K. and Williams, J.A.G. (1998) Luminescent Sensors for pH, pO2, Halide and Hydroxide Ions Using Phenanthridine as a Photosensitiser in Macrocyclic Europium and Terbium Complexes. Journal of the Chemical Society, Perkin Transactions 2, No. 10, 2129-2139. https://doi.org/10.1039/a801270i
Moore, E.G., Bernhardt, P.V., Fuerstenberg, A., Riley, M.J., Smith, T.A. and Vauthey, E. (2005) Tuning the Photophysical Behavior of Luminescent Cyclam Derivatives by Cation Binding and Excited State Redox Potential. Journal of Physical Chemistry A, 109, 3788-3796. https://doi.org/10.1021/jp044221t
Ji, S., Yang, J., Yang, Q., Liu, S., Chen, M. and Zhao, J. (2009) Tuning the Intramolecular Charge Transfer of Alkynylpyrenes: Effect on Photophysical Properties and Its Application in Design of OFF-ON Fluorescent Thiol Probes. Journal of Organic Chemistry, 74, 4855-4865. https://doi.org/10.1021/jo900588e
Aoki, S., Kagata, D., Shiro, M., Takeda, K. and Kimura, E. (2004) Metal Chelation-Controlled Twisted Intramolecular Charge Transfer and Its Application to Fluorescent Sensing of Metal Ions and Anions. Journal of the American Chemical Society, 126, 13377-13390. https://doi.org/10.1021/ja040095v
Collins, G.E., Choi, L.S. and Callahan, J.H. (1998) Effect of Solvent Polarity, pH, and Metal Complexation on the Triple Fluorescence of 4-(N-1, 4, 8, 11-Tetraazacyclotetradecyl) Benzonitrile. Journal of the American Chemical Society, 120, 1474-1478.
Letard, J.F., Lapouyade, R. and Rettig, W. (1993) Synthesis and Photophysical Study of 4-(N-Monoaza-15-Crown-5) Stilbenes Forming TICT States and Their Complexation with Cations. Pure and Applied Chemistry, 65, 1705-1712.
Grabowski, Z.R., Rotkiewicz, K. and Siemiarczuk, A. (1979) Dual Fluorescence of Donor-Acceptor Molecules and the Twisted Intramolecular Charge Transfer (TICT) States. Journal of Luminescence, 18-19, 420-424.
Cazeau-Dubroca, C., Ait Lyazidi, S., Cambou, P., Peirigua, A., Cazeau, P. and Pesquer, M. (1989) Twisted Internal Charge-Transfer Molecules: Already Twisted in the Ground State. Journal of Physical Chemistry A, 93, 2347-2358.
Kim, Y.H., Cho, D.W., Yoon, M. and Kim, D. (1996) Observation of Hydrogen Bonding Effects on Twisted Intramolecular Charge Transfer of p-(N, N-Dimethylamino) Benzoic Acid in Aqueous Cyclodextrin Solutions. Journal of Physical Chemistry A, 100, 15670-15676. https://doi.org/10.1021/jp9613652
Kim, Y., Cheon, H.W., Yoon, M., Song, N.W. and Kim, D. (1997) SiO2 Colloidal Effects on the Twisted Intramolecular Charge Transfer of p-N, N-Dimethylamino- benzoic Acid in Acetonitrile. Chemical Physics Letters, 264, 673-679.