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The Design, Synthesis and Spectroscopic/Photophysical Characterization of Phosphonate-substituted BODIPY

Year 2020, Volume: 48 Issue: 2, 197 - 201, 19.04.2020
https://doi.org/10.15671/hjbc.650747

Abstract

BODIPY compounds continue to attract the attention of
scientists from multidisciplinary areas because of the wide range applications
and excellent photophysical properties as fluorescent sensors or dyes. In this
study, a new phosphonate substituted BODIPY dye was synthesized by classical
condensation-oxidation-complexation method of pyrrolic compounds and aldehyde.
The structure and photophysical properties of the synthesized BODIPY compound
were determined by 1H NMR, 13C NMR, 31P NMR, 19F
NMR, UV-Vis absorption and fluorescence spectroscopic techniques.

0000-0002-0316-4604

Thanks

The author indebted to Prof. Dr. Canan Ünaleroğlu for supplying the laboratory facilities.

References

  • Referans 1 N. Boens, V. Leen, W. Dehaen, Fluorescent indicators based on BODIPY, Chem. Soc. Rev., 41 (2012) 1130-1172. https://pubs.rsc.org/en/content/articlelanding/2012/cs/c1cs15132kReferans 2 A. Loudet, K. Burgess, BODIPY Dyes and Their Derivatives: Syntheses and Spectroscopic Properties, Chem. Rev., 107 (2007) 4891-4932. https://pubs.acs.org/doi/pdf/10.1021/cr078381nReferans 3 G. Ulrich, R. Ziessel, A. Harriman, The Chemistry of Fluorescent Bodipy Dyes: Versatility Unsurpassed, Angew. Chem. Int. Ed., 47 (2008) 1184-1201. https://onlinelibrary.wiley.com/doi/epdf/10.1002/anie.200702070Referans 4 S. Banfi, G. Nasini, S. Zaza, E. Caruso, Synthesis and photo-physical properties of a series of BODIPY dyes, Tetrahedron 69 (2013) 4845-4856. https://www.sciencedirect.com/science/article/pii/S0040402013006029Referans 5 A. Treibs, F.-H. Kreuzer, Difluorboryl-Komplexe von Di- und Tripyrrylmethenen, Justus Liebigs Ann. Chem., 718 (1968) 208-223. https://onlinelibrary.wiley.com/doi/abs/10.1002/jlac.19687180119Referans 6 A. V. Solomonov, Y. S. Marfin, E. V. Rumyantsev, Design and applications of dipyrrin-based fluorescent dyes and related organic luminophores: From individual compounds to supramolecular self-assembled systems, Dyes and Pigments, 162 (2019) 517-542. https://www.sciencedirect.com/science/article/pii/S0143720818304698Referans 7 P. Kaur, K. Singh, Recent advances in the application of BODIPY in bioimaging and chemosensing, J. Mater. Chem. C, 7 (2019) 11361-11405. https://pubs.rsc.org/en/content/articlelanding/2019/tc/c9tc03719Referans 8 T. Bura, R. Ziessel, Water-Soluble Phosphonate-Substituted BODIPY Derivatives with Tunable Emission Channels, Org. Lett., 13 (2011) 3072-3075. https://pubs.acs.org/doi/10.1021/ol200969rReferans 9 A.-C. Schulz-Fincke, M. Blaut, A. Braune, M. Gütschow, A BODIPY-Tagged Phosphono Peptide as Activity-Based Probe for Human Leukocyte Elastase, ACS Med. Chem. Lett., 9 (2018) 345-350. https://pubs.acs.org/doi/abs/10.1021/acsmedchemlett.7b00533Referans 10 Z. Dost, S. Atilgan, E. U. Akkaya, Distyryl-boradiazaindacenes: facile synthesis of novelnear IR emitting fluorophores, Tetrahedron, 62 (2006) 8484–8488. https://www.sciencedirect.com/science/article/pii/S0040402006010258Referans 11 B. Brizet, C. Bernhard, Y. Volkova, Y. Roussselin, P. D. Harvey, C. Goze, F. Denat, Boron functionalization of BODIPY by various alcohols and phenols, Org. Biomol. Chem., 11 (2013) 7729-7737. https://pubs.rsc.org/en/content/articlelanding/2013/ob/c3ob41370
Year 2020, Volume: 48 Issue: 2, 197 - 201, 19.04.2020
https://doi.org/10.15671/hjbc.650747

Abstract

References

  • Referans 1 N. Boens, V. Leen, W. Dehaen, Fluorescent indicators based on BODIPY, Chem. Soc. Rev., 41 (2012) 1130-1172. https://pubs.rsc.org/en/content/articlelanding/2012/cs/c1cs15132kReferans 2 A. Loudet, K. Burgess, BODIPY Dyes and Their Derivatives: Syntheses and Spectroscopic Properties, Chem. Rev., 107 (2007) 4891-4932. https://pubs.acs.org/doi/pdf/10.1021/cr078381nReferans 3 G. Ulrich, R. Ziessel, A. Harriman, The Chemistry of Fluorescent Bodipy Dyes: Versatility Unsurpassed, Angew. Chem. Int. Ed., 47 (2008) 1184-1201. https://onlinelibrary.wiley.com/doi/epdf/10.1002/anie.200702070Referans 4 S. Banfi, G. Nasini, S. Zaza, E. Caruso, Synthesis and photo-physical properties of a series of BODIPY dyes, Tetrahedron 69 (2013) 4845-4856. https://www.sciencedirect.com/science/article/pii/S0040402013006029Referans 5 A. Treibs, F.-H. Kreuzer, Difluorboryl-Komplexe von Di- und Tripyrrylmethenen, Justus Liebigs Ann. Chem., 718 (1968) 208-223. https://onlinelibrary.wiley.com/doi/abs/10.1002/jlac.19687180119Referans 6 A. V. Solomonov, Y. S. Marfin, E. V. Rumyantsev, Design and applications of dipyrrin-based fluorescent dyes and related organic luminophores: From individual compounds to supramolecular self-assembled systems, Dyes and Pigments, 162 (2019) 517-542. https://www.sciencedirect.com/science/article/pii/S0143720818304698Referans 7 P. Kaur, K. Singh, Recent advances in the application of BODIPY in bioimaging and chemosensing, J. Mater. Chem. C, 7 (2019) 11361-11405. https://pubs.rsc.org/en/content/articlelanding/2019/tc/c9tc03719Referans 8 T. Bura, R. Ziessel, Water-Soluble Phosphonate-Substituted BODIPY Derivatives with Tunable Emission Channels, Org. Lett., 13 (2011) 3072-3075. https://pubs.acs.org/doi/10.1021/ol200969rReferans 9 A.-C. Schulz-Fincke, M. Blaut, A. Braune, M. Gütschow, A BODIPY-Tagged Phosphono Peptide as Activity-Based Probe for Human Leukocyte Elastase, ACS Med. Chem. Lett., 9 (2018) 345-350. https://pubs.acs.org/doi/abs/10.1021/acsmedchemlett.7b00533Referans 10 Z. Dost, S. Atilgan, E. U. Akkaya, Distyryl-boradiazaindacenes: facile synthesis of novelnear IR emitting fluorophores, Tetrahedron, 62 (2006) 8484–8488. https://www.sciencedirect.com/science/article/pii/S0040402006010258Referans 11 B. Brizet, C. Bernhard, Y. Volkova, Y. Roussselin, P. D. Harvey, C. Goze, F. Denat, Boron functionalization of BODIPY by various alcohols and phenols, Org. Biomol. Chem., 11 (2013) 7729-7737. https://pubs.rsc.org/en/content/articlelanding/2013/ob/c3ob41370
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Details

Primary Language English
Subjects Engineering
Journal Section Articles
Authors

Dilek Işık Taşgın 0000-0002-0316-4604

Publication Date April 19, 2020
Acceptance Date April 19, 2020
Published in Issue Year 2020 Volume: 48 Issue: 2

Cite

APA Işık Taşgın, D. (2020). The Design, Synthesis and Spectroscopic/Photophysical Characterization of Phosphonate-substituted BODIPY. Hacettepe Journal of Biology and Chemistry, 48(2), 197-201. https://doi.org/10.15671/hjbc.650747
AMA Işık Taşgın D. The Design, Synthesis and Spectroscopic/Photophysical Characterization of Phosphonate-substituted BODIPY. HJBC. April 2020;48(2):197-201. doi:10.15671/hjbc.650747
Chicago Işık Taşgın, Dilek. “The Design, Synthesis and Spectroscopic/Photophysical Characterization of Phosphonate-Substituted BODIPY”. Hacettepe Journal of Biology and Chemistry 48, no. 2 (April 2020): 197-201. https://doi.org/10.15671/hjbc.650747.
EndNote Işık Taşgın D (April 1, 2020) The Design, Synthesis and Spectroscopic/Photophysical Characterization of Phosphonate-substituted BODIPY. Hacettepe Journal of Biology and Chemistry 48 2 197–201.
IEEE D. Işık Taşgın, “The Design, Synthesis and Spectroscopic/Photophysical Characterization of Phosphonate-substituted BODIPY”, HJBC, vol. 48, no. 2, pp. 197–201, 2020, doi: 10.15671/hjbc.650747.
ISNAD Işık Taşgın, Dilek. “The Design, Synthesis and Spectroscopic/Photophysical Characterization of Phosphonate-Substituted BODIPY”. Hacettepe Journal of Biology and Chemistry 48/2 (April 2020), 197-201. https://doi.org/10.15671/hjbc.650747.
JAMA Işık Taşgın D. The Design, Synthesis and Spectroscopic/Photophysical Characterization of Phosphonate-substituted BODIPY. HJBC. 2020;48:197–201.
MLA Işık Taşgın, Dilek. “The Design, Synthesis and Spectroscopic/Photophysical Characterization of Phosphonate-Substituted BODIPY”. Hacettepe Journal of Biology and Chemistry, vol. 48, no. 2, 2020, pp. 197-01, doi:10.15671/hjbc.650747.
Vancouver Işık Taşgın D. The Design, Synthesis and Spectroscopic/Photophysical Characterization of Phosphonate-substituted BODIPY. HJBC. 2020;48(2):197-201.

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