RAS Chemistry & Material ScienceЖурнал органической химии Russian Journal of Organic Chemistry

  • ISSN (Print) 0514-7492
  • ISSN (Online) 3034-6304

Synthesis of N,N',N"-Triaryl Derivatives of Tris(3-aminopropyl)amine and Their Study as Fluorescent Detectors of Metal Cations

PII
S3034630425070213-1
DOI
10.7868/S3034630425070213
Publication type
Article
Status
Published
Authors
Volume/ Edition
Volume 61 / Issue number 7
Pages
1008-1018
Abstract
Palladium-catalyzed arylation of tris(3-aminopropyl)amine (TRPN) with several halogen-substituted naphthalene, anthracene, phenanthrene, and pyrene was studied. As a result, corresponding N,N,N"-triaryl derivatives were synthesized, and the best yields of the target compounds were obtained in the reactions with 1-chloro- and 9-bromoanthracenes. Fluorescence spectra of these compounds were studied in the presence of metal cations which showed that complete or very strong quenching of emission was observed upon the addition of Cu(II), Al(III), Cr(III) perchlorates in the case of 1-naphthyl-, 2-anthryl-, and 9-phenanthrenyl derivatives of TRPN. For 1-pyrenyl derivative complete quenching of fluorescence took place only in the presence of copper cations. For a number of other metal cations, slight changes in the emission intensity were observed with hypsochromic shifts of the maximum by approximately 10 nm. The characteristic changes in the absorption spectra of compounds 2, 5, 8 were observed in the presence of Cu(II), Al(III), and Cr(III) cations, which make these compounds promising for fluorescent and spectrophotometric detection of Cu(II), Al(III), and Cr(III) cations.
Keywords
полиамины аминирование палладиевый катализ конденсированные ароматические соединения флуоресценция детектирование
Date of publication
01.07.2025
Year of publication
2025
Number of purchasers
0
Views
22

References

  1. 1. Tawfik S.M., Farag A.A., Abd-Elaal A.A. J. Fluorescence, 2024, 34, 2139–2155. https://doi.org/10.1007/s10895-023-03426-6
  2. 2. Dathees T.J., Makarios Paul S.M., Sanmugam A. et al. Spectrochim Acta A Mol. Biomol. Spectrosc., 2024, 308, 123732. https://doi.org/10.1016/j.saa.2023.123732
  3. 3. Lin Q., Yang Q.P., Sun B. et al. Chin. J. Chem., 2014, 32, 1255–1258. https://doi.org/10.1002/cjoc.201400601
  4. 4. Zhu J., Zhang Y., Wang L., et al. Tetrahedron Lett., 2016, 57, 3535–3539. https://doi.org/10.1016/j.tetlet.2016.06.112
  5. 5. Hsieh W.H., Wan C.-F., Liao D.-J., Wu A.-T. Tetrahedron Lett., 2012, 53, 5848–5851. https://doi.org/10.1016/j.tetlet.2012.08.058
  6. 6. Misra A., Shahid M., Srivastava P., Dwivedi P. J. Inclusion Phenom. Macrocyclic Chem., 2011, 69, 119–129. https://doi.org/10.1007/s10847-010-9821-5
  7. 7. Chaichana K., Phutlaprungrueang N., Chaicharo-enwimolkul L., et al. Spectrochim Acta A Mol. Biomol. Spectrosc., 2019, 207, 118–122. https://doi.org/10.1016/j.saa.2018.09.006
  8. 8. Lee H.G., Kim K.B., Park G.J. et al. Inorg. Chem. Commun., 2014, 39, 61–65. https:/.doi.org/10.1016/j.inoche.2013.10.049
  9. 9. Wang Y., Qian G., Xiao Z. et al. Inorg. Chim. Acta, 2010, 363, 2325–2332. https://doi.org/10.1016/j.ica.2010.03.065
  10. 10. Tümay S.O., Haddad Irani-nezhad M., Khataee A. J. Photochem. Photobiology A, 2020, 402, 112819. https://doi.org/10.1016/j.jphotochem.2020.112819
  11. 11. Shiraishi Y., Kohno Y., Hirai T. J. Phys. Chem. B, 2005, 109, 19139–19147. https://doi.org/10.1021/jp052645x
  12. 12. Tamayo A., Oliveira E., Covelo B. et al. Z. Anorg. Allg. Chem., 2007, 633, 1809–1814. https://doi.org/10.1002/zaac.200700164
  13. 13. Mameli M., Lippolis V., Caltagirone C. et al. Inorg. Chem., 2010, 49, 8276–8286. https://doi.org/10.1021/ic1007439
  14. 14. Şahin Ö., Şahin M., Koçak N., Yilmaz M. Turkish J. Chem., 2013, 37, 832–839. https://doi.org/10.3906/kim-1302-77
  15. 15. Kumar A., Ali A., Rao C.P. J. Photochem. Photobiology A, 2006, 177, 164–169. https://doi.org/10.1016/j.jphotochem.2005.05.021
  16. 16. Kumar M., Babu J.N., Bhalla V. J. Inclusion Phenom. Macrocyclic Chem., 2010, 66, 139–145. https://doi.org/10.1007/s10847-009-9670-2
  17. 17. Yoon J., Ohler N.E., Vance D.H. et al. Tetrahedron Lett., 1997, 38, 3845–3848. https://doi.org/10.1016/S0040-4039 (97)00768-5
  18. 18. Xie G.-Y., Jianga L., Lu T.-B. RSC Adv., 2012, 2, 12728–12731. https://doi.org/10.1039/C2RA22423B
  19. 19. Wu Y.-S., Li C.-Y., Li Y.-F. et al. Sensor. Actuators: B, 2016, 222, 1226–1232. https://doi.org/10.1016/j.snb.2015.06.151
  20. 20. Fernández-Lodeiro J., Núñez C., de Castro C.S. et al. Inorg. Chem., 2013, 52, 121–129. https://doi.org/10.1021/ic301365y
  21. 21. Jun E.J., Won H.N., Kim J.S. et al. Tetrahedron Lett., 2006, 47, 4577–4580. https://doi.org/10.1016/j.tetlet.2006.04.143
  22. 22. Kumar M., Kumar N., Bhalla V. Dalton Trans., 2012, 41, 10189–10193. https://doi.org/10.1039/c2dt31081c
  23. 23. Passaniti P., Maestri M., Ceroni P. Photochem. Photobiol. Sci., 2007, 6, 471–479. https://doi.org/10.1039/B613944B
  24. 24. Kavallieratos F., Sabucedo A., Pau A., Rodriguez J. J. Am. Soc. Mass. Spectrom., 2005, 16, 1377–1383. https://doi.org/10.1016/j.jasms.2005.04.008
  25. 25. Arnold G.J., Van Arman S.A. Tetrahedron Lett., 1997, 38, 4745–4748. https://doi.org/10.1016/S0040-4039 (97)01027-7
  26. 26. Averin A.D., Uglov A.N., Beletskaya I.P. et al. Pd-catalyzed arylation of polyamines. In: Advances in Chemistry Research. Nova Science Pubs. 2010, 4, 269–296.
  27. 27. Averin A.D., Kobelev S.M., Anokhin M.V. et al. Palladium-catalyzed amination reaction in the synthesis of nitrogenand oxygen-containing macrocycles and macropolycycles. In: Targets in Heterocyclic Systems: Chemistry and Properties, Eds. O.A. Attanasi, D. Spinelli. 2011, 15, 193–225.
  28. 28. Averin A.D., Abel A.S., Malysheva A.S. et al. Macroheterocycles, 2023, 16, 92. https://doi.org/10.6060/mhc235004a
  29. 29. Stoikov I.I., Antipin I.S., Burilov V.A. et al. Russ. J. Org. Chem., 2024, 60, 1361–1584. https://doi.org/10.1134/S1070428024100257
  30. 30. Kuliukhina D.S., Chernichenko N.M., Averin A.D. et al. Chemosensors, 2023, 11, 186. https://doi.org/10.3390/chemosensors11030186
  31. 31. Ukai T., Kawazura H., Ishii Y. et al. J. Organomet. Chem., 1974, 65, 253–266. https://doi.org/10.1016/S0022-328X (00)91277-4
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