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Synthesis and photophysical investigation of AIEgen dyes bearing quinoline and BODIPY scaffolds

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Chemistry of Heterocyclic Compounds Aims and scope

Quinoline-based BODIPY AIEgen dyes were synthesized and the structures were elucidated by 1H, 13C, 19F NMR, FT-IR spectroscopy and mass spectrometry methods. Their photophysical properties were investigated. The dyes showed fluorescence quantum yield in the range of 0.16–1.29% in MeOH. It was found that the presence of methoxy group and tetrazole moiety led to blue and red spectral shift, respectively, of the UV absorption maxima of these dyes compared to their chloroquinoline analog. Stokes shifts of the dyes were in the range of 637–955 cm–1. Aggregation-induced emission behavior of the dyes was investigated in EtOH–H2O mixture so that the dyes exhibited 1.6- to 2.3-fold fluorescence enhancement.

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References

  1. Arslan, B. S.; Güzel, E.; Kaya, T.; Durmaz, V.; Keskin, M.; Avcı, D.; Nebioğlu, M.; Şişman, İ. Dyes Pigm. 2019, 164, 188.

    Article  CAS  Google Scholar 

  2. Gupta, S. S.; Kumari, S.; Kumar, I.; Sharma, U. Chem. Heterocycl. Compd. 2020, 56, 433. [Khim. Geterotsikl. Soedin. 2020, 56, 433.]

  3. Prajapati, S. M.; Patel, K. D.; Vekariya, R. H.; Panchal, S. N.; Patel, H. D. RSC Adv. 2014, 4, 24463.

    Article  CAS  Google Scholar 

  4. Liu, Y.; Yang, L.; Ma, C.; Tang, A. Dyes Pigm. 2020, 173, 107981.

    Article  CAS  Google Scholar 

  5. Wang, L.; Qian, Y. A. J. Photochem. Photobiol., A 2019, 372, 122.

    Article  CAS  Google Scholar 

  6. Benelhadj, K.; Retailleau, P.; Massue, J.; Ulrich, G. Tetrahedron Lett. 2016, 57, 1976.

    Article  CAS  Google Scholar 

  7. Matsuoka, R.; Nabeshima, T. Front. Chem. 2018, 6, 349.

    Article  Google Scholar 

  8. Dudina, N. A.; Nikonova, A. Y.; Antina, Y. V.; Berezin, M. B.; Vyugin, A. I. Chem. Heterocycl. Compd. 2014, 49, 1740. [Khim. Geterotsikl. Soedin. 2013, 1878.]

  9. Treibs, A.; Kreuzer, F. H. Justus Liebigs Ann. Chem. 1968, 718, 208.

    Article  CAS  Google Scholar 

  10. Boens, N.; Leen, V.; Dehaen, W. Chem. Soc. Rev. 2012, 41, 1130.

    Article  CAS  Google Scholar 

  11. Boens, N.; Verbelen, B.; Ortiz, M. J.; Jiao, L.; Dehaen, W. Coord. Chem. Rev. 2019, 399, 213024.

    Article  CAS  Google Scholar 

  12. Loudet, A.; Burgess, K. Chem. Rev. 2007, 107, 4891.

    Article  CAS  Google Scholar 

  13. Gao, J.; Tao, Y.; Wang, N.; He, J.; Zhang, J.; Zhao, W. Spectrochim. Acta, Part A 2018, 203, 77.

    Article  CAS  Google Scholar 

  14. Qin, W.; Dou, W.; Leen, V.; Dehaen, W.; Van der Auweraer, M.; Boens, N. A. RSC Adv. 2016, 6, 7806.

    Article  CAS  Google Scholar 

  15. Kamkaew, A.; Lim, S. H.; Lee, H. B.; Kiew, L. V.; Chung, L. Y.; Burgess, K. Chem. Soc. Rev. 2013, 42, 77.

    Article  CAS  Google Scholar 

  16. Yadav, R. K.; Baeg, J. O.; Kumar, A.; Kong, K. J.; Oh, G. H.; Park, N. J. J. Mater. Chem. A 2014, 2, 5068.

    Article  CAS  Google Scholar 

  17. Yang, H.; Zhao, M.; Zhang, J.; Ma, J.; Wu, P.; Liu, W.; Wen, L. J. Mater. Chem. A 2019, 7, 20742.

    Article  CAS  Google Scholar 

  18. Thumuganti, G.; Gupta, V.; Singh, S. P. New J. Chem. 2019, 43, 8735.

    Article  CAS  Google Scholar 

  19. Luo, J.; Xie, Z.; Xie, Z.; Lam, J. W. Y.; Cheng, L.; Chen, H.; Qiu, C.; Kwok, H. S.; Zhan, X.; Liu, Y.; Zhu, D.; Tang, B. Z. Chem. Commun. 2001, 1740.

  20. Yamaguchi, M.; Ito, S.; Hirose, A.; Tanaka, K.; Chujo, Y. Mater. Chem. Front. 2017, 1, 1573.

    Article  CAS  Google Scholar 

  21. Cheng, B.; Xu, J. Phosphorus, Sulfur Silicon Relat. Elem. 2017, 192, 518.

    Article  CAS  Google Scholar 

  22. Meth-Cohn, O.; Narine, B.; Tarnowski, B.; Hayes, R.; Keyzad, A.; Rhouati, S.; Robinson, A. A. J. Chem. Soc., Perkin Trans. 1 1981, 2509.

  23. Chandraprakash, K.; Ramesh, P.; Ravichandran, K.; Mohan, P. S.; Ponnuswamy, M. N. Acta Crystallogr., Sect. E: Struct. Rep. Online 2010, 66, o2510.

    Google Scholar 

  24. Ladani, N. K.; Patel, M. P.; Patel, R. G. ARKIVOC 2009, (vii), 292.

  25. Singh, R. S.; Gupta, R. K.; Paitandi, R. P.; Dubey, M.; Sharma, G.; Koch, B.; Pandey, D. S. Chem. Commun. 2015, 9125.

  26. Choi, S.; Bouffard, J.; Kim, Y. Chem. Sci. 2014, 5, 751.

    Article  CAS  Google Scholar 

  27. Prasannan, D.; Raghav, D.; Sujatha, S.; Hareendrakrishna Kumar, H.; Rathinasamy, K.; Arunkumar, C. RSC Adv. 2016, 6, 80808.

    Article  CAS  Google Scholar 

  28. Sørensen, M. L. H.; Vosch, T.; Laursen, B. W.; Hansen, T. Photochem. Photobiol. Sci. 2019, 18, 1315.

    Article  Google Scholar 

  29. Patalag, L. J.; Jones, P. G.; Werz, D. B. Chem.–Eur. J. 2017, 23, 15903.

    Article  CAS  Google Scholar 

  30. Patalag, L. J.; Loch, M.; Jones, P. G.; Werz, D. B. J. Org. Chem. 2019, 84, 7804.

    Article  CAS  Google Scholar 

  31. Dumas-Verdes, C.; Miomandre, F.; Lépicier, E.; Galangau, O.; Vu, T. T.; Clavier, G.; Méallet-Renault, R.; Audebert, P. Eur. J. Org. Chem. 2010, 2525.

  32. Duran-Sampedro, G.; Agarrabeitia, A. R.; Garcia-Moreno, I.; Costela, A.; Bañuelos, J.; Arbeloa, T.; López Arbeloa, I.; Chiara, J. L.; Ortiz, M. J. Eur. J. Org. Chem. 2012, 6335.

  33. Zhang, X. F.; Zhang, I.; Liu, L. Photochem. Photobiol. 2010, 86, 492.

    Article  CAS  Google Scholar 

  34. Rohand, T.; Baruah, M.; Qin, W.; Boens, N.; Dehaen, W. Chem. Commun. 2006, 266.

  35. Qin, W.; Rohand, T.; Baruah, M.; Stefan, A.; Van der Auweraer, M.; Dehaen, W.; Boens, N. Chem. Phys. Lett. 2006, 420, 562.

  36. Singh, R. S.; Kumar, A.; Mukhopadhyay, S.; Sharma, G.; Koch, B.; Pandey, D. S. J. Phys. Chem. C 2016, 120, 22605.

    Article  CAS  Google Scholar 

  37. Qian, J.; Tang, B. Z. Chem 2017, 3, 56.

    Article  CAS  Google Scholar 

  38. Goud, T. V.; Tutar, A.; Biellmann, J. F. Tetrahedron 2006, 62, 5084.

    Article  CAS  Google Scholar 

  39. Neena, K. K.; Thilagar, P. ChemPlusChem 2016, 81, 955.

    Article  CAS  Google Scholar 

  40. Benniston, A. C.; Copley, G.; Elliott, K. J.; Harrington, R. W.; Clegg, W. Eur. J. Org. Chem. 2008, 2705.

  41. Armarego, W. L. F. Purification of Laboratory Chemicals; Elsevier: Amsterdam, 2008, 8th ed.

  42. Swinehart, F. J. Chem. Educ. 1962, 39, 333.

    Article  CAS  Google Scholar 

  43. Casey, K. G.; Quitevis, E. L. J. Phys. Chem. 1988, 92, 6590.

    Article  CAS  Google Scholar 

  44. Rurack, K.; Spieles, M. Anal. Chem. 2011, 83, 1232.

    Article  CAS  Google Scholar 

  45. Derin, Y.; Yılmaz, R. F.; Baydilek, İ. H.; Atalay, V. E.; Özdemir, A.; Tutar, A. Inorg. Chim. Acta 2018, 482, 130.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Arts and Sciences, Sakarya University, 54050, Sakarya, Turkey

    Yavuz Derin, Barış Seçkin Arslan, Büşra Albayrak Mısır, İlkay Şişman, Mehmet Nebioğlu & Ahmet Tutar

  2. Biomedical, Magnetic and Semiconductor Materials Research Center (BIMAS-RC), Sakarya University, 54050, Sakarya, Turkey

    İlkay Şişman & Mehmet Nebioğlu

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  1. Yavuz Derin
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  2. Barış Seçkin Arslan
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  3. Büşra Albayrak Mısır
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  4. İlkay Şişman
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  5. Mehmet Nebioğlu
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  6. Ahmet Tutar
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Correspondence to Yavuz Derin or Barış Seçkin Arslan.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(12), 1542–1547

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Derin, Y., Arslan, B.S., Mısır, B.A. et al. Synthesis and photophysical investigation of AIEgen dyes bearing quinoline and BODIPY scaffolds. Chem Heterocycl Comp 56, 1542–1547 (2020). https://doi.org/10.1007/s10593-020-02847-6

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  • DOI: https://doi.org/10.1007/s10593-020-02847-6

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