Fosfonat-substitüye BODIPY Tasarımı, Sentezi ve Spektroskopik/Fotofiziksel Karakterizasyonu

BODIPY bileşikleri floresan sensör veya boya olarak geniş kullanım alanına sahip olması ve üstün fotofiziksel özelliklerinden dolayı multidisipliner alanlardaki bilim insanlarının ilgisini çekmeye devam etmektedir. Bu çalışmada, yeni bir fosfonat-substitüye BODIPY boyası, pirol ve aldehitten kondenzasyon-yükseltgenme-kompleksleşme metodu kullanılarak sentezlenmiştir. Sentezlenen BODIPY bileşiğinin yapısı ve fotofiziksel özellikleri 1 H NMR, 13C NMR, 31P NMR, 19F NMR, UV-Vis absorpsiyon ve floresans spektroskopi teknikleriyle tanımlanmıştır.

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

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

___

  • 1. N. Boens, V. Leen, W. Dehaen, Fluorescent indicators based on BODIPY, Chem. Soc. Rev., 41 (2012) 1130-1172.
  • 2. A. Loudet, K. Burgess, BODIPY Dyes and Their Derivatives: Syntheses and Spectroscopic Properties, Chem. Rev., 107 (2007) 4891-4932.
  • 3. G. Ulrich, R. Ziessel, A. Harriman, The Chemistry of Fluorescent Bodipy Dyes: Versatility Unsurpassed, Angew. Chem. Int. Ed., 47 (2008) 1184-1201.
  • 4. S. Banfi, G. Nasini, S. Zaza, E. Caruso, Synthesis and photophysical properties of a series of BODIPY dyes, Tetrahedron 69 (2013) 4845-4856.
  • 5. A. Treibs, F.-H. Kreuzer, Difluorboryl-Komplexe von Di- und Tripyrrylmethenen, Justus Liebigs Ann. Chem., 718 (1968) 208-223.
  • 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.
  • 7. P. Kaur, K. Singh, Recent advances in the application of BODIPY in bioimaging and chemosensing, J. Mater. Chem. C, 7 (2019) 11361-11405.
  • 8. T. Bura, R. Ziessel, Water-Soluble Phosphonate-Substituted BODIPY Derivatives with Tunable Emission Channels, Org. Lett., 13 (2011) 3072-3075.
  • 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.
  • 10. Z. Dost, S. Atilgan, E. U. Akkaya, Distyryl-boradiazaindacenes: facile synthesis of novelnear IR emitting fluorophores, Tetrahedron, 62 (2006) 8484–8488.
  • 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.