全部 标题 作者
关键词 摘要

OALib Journal期刊
ISSN: 2333-9721
费用:99美元

查看量下载量

Study of the Double Fluorescence of a New Anthracene (13)aneN4

DOI: 10.4236/oalib.1110474, PP. 1-9

Subject Areas: Organic Chemistry

Keywords: Tetraazacycloalcane, Fluorescence, Charge Transfer, pH Sensor, Double Fluorescence, Anthracene, Metals Coordination

Full-Text   Cite this paper   Add to My Lib

Abstract

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.

References

[1]  Liang, X. and Sadler, P.S. (2004) Cyclam Complexes and Their Applications in Medicine. Chemical Society Reviews, 33, 246-260. https://doi.org/10.1039/b313659k
[2]  Bagnoud, M.A., Haerdi, W. and Veuthey, J.L. (1990) Outer-Sphere Ligand-Exchange Chromatography with Copper-Loaded Macrocyclic-Bonded Silica Column. Chromatographia, 29, 495-499. https://doi.org/10.1007/BF02261400
[3]  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. https://doi.org/10.1016/S0010-8545(98)00169-6
[4]  Sibert, J.W., Cory, A.H. and Cory, J.G. (2002) Lipophilic Derivatives of Cyclam as New Inhibitors of Tumor Cell Growth. Chemical Communications, No. 2, 154-155. https://doi.org/10.1039/b107899m
[5]  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
[6]  Bahut, J., Benda, L., Kotek, J., Pintacuda, G. and Hermann, P. (2020) Paramagnetic Cobalt (II) Complexes with Cyclam Derivatives: Toward 19F MRI Contrast Agents. Inorganic Chemistry, 59, 10071-10082. https://doi.org/10.1021/acs.inorgchem.0c01216
[7]  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
[8]  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
[9]  Brandes, S., Denat, F., Meyer, M. and Guilard, R. (2005) De la molécule au procédé. https://new.societechimiquedefrance.fr/wp-content/uploads/2019/12/2005-290-291-oct-nov-Guilard-p.108.pdf
[10]  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. https://patentimages.storage.googleapis.com/4a/72/5e/123e4fbdf71d46/WO2008099114A2.pdf
[11]  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
[12]  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. https://doi.org/10.1021/acs.inorgchem.9b00995
[13]  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
[14]  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
[15]  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
[16]  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
[17]  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
[18]  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
[19]  Valeur, B. (2004) Invitation à la fluorescence moléculaire. De Boeck, Bruxelles.
[20]  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
[21]  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. https://doi.org/10.1021/ja972169r
[22]  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. https://doi.org/10.1351/pac199365081705
[23]  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. https://doi.org/10.1016/0022-2313(79)90153-4
[24]  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. https://doi.org/10.1021/j100343a030
[25]  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
[26]  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. https://doi.org/10.1016/S0009-2614(96)01388-7

Full-Text


comments powered by Disqus

Contact Us

service@oalib.com

QQ:3279437679

WhatsApp +8615387084133

WeChat 1538708413