Efficient deprotection of F-BODIPY derivatives: removal of BF2 using Brønsted acids

Mingfeng Yu, Joseph K.-H. Wong, Cyril Tang, Peter Turner, Matthew H. Todd and Peter J. Rutledge
Beilstein J. Org. Chem. 2015, 11, 37–41. https://doi.org/10.3762/bjoc.11.6

Supporting Information

Supporting Information File 1: Experimental procedures and characterization data; crystallographic information for 8; 1H, 13C, 11B & 19F NMR spectra of novel compounds 3, 4, 14, 15, 1618; LC–MS trace of crude 18.
Format: PDF Size: 1.9 MB Download
Supporting Information File 2: CIF file of 8, CCDC 1018518.
Format: CIF Size: 21.5 KB Download

Cite the Following Article

Efficient deprotection of F-BODIPY derivatives: removal of BF2 using Brønsted acids
Mingfeng Yu, Joseph K.-H. Wong, Cyril Tang, Peter Turner, Matthew H. Todd and Peter J. Rutledge
Beilstein J. Org. Chem. 2015, 11, 37–41. https://doi.org/10.3762/bjoc.11.6

How to Cite

Yu, M.; Wong, J. K.-H.; Tang, C.; Turner, P.; Todd, M. H.; Rutledge, P. J. Beilstein J. Org. Chem. 2015, 11, 37–41. doi:10.3762/bjoc.11.6

Download Citation

Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window below.
Citation data in RIS format can be imported by all major citation management software, including EndNote, ProCite, RefWorks, and Zotero.

Citations to This Article

Up to 20 of the most recent references are displayed here.

Scholarly Works

  • Knoll, S.; Zens, C.; Maisuradze, T.; Schmidt, H.; Kupfer, S.; Zedler, L.; Dietzek-Ivanšić, B.; Streb, C. Light-Induced Charge Separation in Covalently Linked BODIPY-Quinone-Alkyne Dyads. Chemistry (Weinheim an der Bergstrasse, Germany) 2024, e202303250. doi:10.1002/chem.202303250
  • Hu, C.; Wen, L.; Yan, J.; Su, P.; Li, F.; Zheng, K.; Zhang, N. Use of BOPYOs as a protection strategy for Pyrrole-based Chalcones: Removal of BF2, optical properties and AIE effect. Journal of Molecular Structure 2023, 1272, 134090. doi:10.1016/j.molstruc.2022.134090
  • Blázquez-Moraleja, A.; Maierhofer, L.; Mann, E.; Prieto-Montero, R.; Oliden-Sánchez, A.; Celada, L.; Martínez-Martínez, V.; Chiara, M.-D.; Chiara, J. L. Acetoxymethyl-BODIPY dyes: a universal platform for the fluorescent labeling of nucleophiles. Organic Chemistry Frontiers 2022, 9, 5774–5789. doi:10.1039/d2qo01099b
  • Clarke, R. G.; Weatherston, J.; Taj‐Aldeen, R. A.; Waddell, P. G.; McFarlane, W.; Penfold, T. J.; Bogaerts, J.; Herrebout, W.; Mackenzie, L. E.; Pal, R.; Hall, M. J. Synthesis and Structural Diversification of Circularly Polarised Luminescence Active, Helically Chiral, "Confused" N,N,O,C‐BODIPYs**. ChemPhotoChem 2022, 7. doi:10.1002/cptc.202200194
  • Gapare, R. L.; Thompson, A. Substitution at boron in BODIPYs. Chemical communications (Cambridge, England) 2022, 58, 7351–7359. doi:10.1039/d2cc02362h
  • McDonagh, A. W.; McNeil, B. L.; Rousseau, J.; Roberts, R. J.; Merkens, H.; Yang, H.; Bénard, F.; Ramogida, C. F. Development of a multi faceted platform containing a tetrazine, fluorophore and chelator: synthesis, characterization, radiolabeling, and immuno-SPECT imaging. EJNMMI radiopharmacy and chemistry 2022, 7, 12. doi:10.1186/s41181-022-00164-1
  • Aikman, B.; Bonsignore, R.; Woods, B.; Doellerer, D.; Scotti, R.; Schmidt, C.; Heidecker, A. A.; Pöthig, A.; Sayers, E. J.; Jones, A. T.; Casini, A. Highly-fluorescent BODIPY-functionalised metallacages as drug delivery systems: synthesis, characterisation and cellular accumulation studies. Dalton transactions (Cambridge, England : 2003) 2022, 51, 7476–7490. doi:10.1039/d2dt00337f
  • Stemler, T.; Hoffmann, C.; Hierlmeier, I.; Maus, S.; Krause, E.; Ezziddin, S.; Jung, G.; Bartholomä, M. A Structure-Activity Relationship Study of Bimodal BODIPY-Labeled PSMA-Targeting Bioconjugates. ChemMedChem 2021, 16, 2535–2545. doi:10.1002/cmdc.202100210
  • Smith, C. D.; Thompson, A. Facile deprotection of F-BODIPYs using methylboronic acid. RSC advances 2020, 10, 24273–24279. doi:10.1039/d0ra05151a
  • Shrestha, R.; Petley, E. V.; Farrand, K. J.; Jamieson, S. A.; Jiao, W.; Teesdale-Spittle, P. H.; Mace, P. D.; Hermans, I. F.; Rendle, P. M. The Synthesis and Anti-tumour Properties of Poly Ethoxy Ethyl Glycinamide (PEE-G) Scaffolds with Multiple PD-1 Peptides Attached. ChemMedChem 2020, 15, 1128–1138. doi:10.1002/cmdc.202000221
  • Uriel, C.; Permingeat, C.; Ventura, J.; Avellanal-Zaballa, E.; Bañuelos, J.; García-Moreno, I.; Gómez, A. M.; Lopez, J. C. BODIPYs as Chemically Stable Fluorescent Tags for Synthetic Glycosylation Strategies towards Fluorescently Labeled Saccharides. Chemistry (Weinheim an der Bergstrasse, Germany) 2020, 26, 5388–5399. doi:10.1002/chem.201905780
  • Chowdhury, S.; Rooj, B.; Dutta, A.; Mandal, U. Review on Recent Advances in Metal Ions Sensing Using Different Fluorescent Probes. Journal of fluorescence 2018, 28, 999–1021. doi:10.1007/s10895-018-2263-y
  • Uno, H.; Honda, T.; Kitatsuka, M.; Hiraoka, S.; Mori, S.; Takase, M.; Okujima, T.; Nakae, T. Benzene-fused bis(acenaphthoBODIPY)s, stable near-infrared-selective dyes. RSC advances 2018, 8, 14072–14083. doi:10.1039/c8ra01694a
  • Lau, Y. H.; Clegg, J. K.; Price, J. R.; Macquart, R. B.; Todd, M. H.; Rutledge, P. J. Molecular Switches for any pH: A Systematic Study of the Versatile Coordination Behaviour of Cyclam Scorpionands. Chemistry (Weinheim an der Bergstrasse, Germany) 2017, 24, 1573–1585. doi:10.1002/chem.201703488
  • Stewart, B.; Kogej, K.; Ramos, M. L.; Valente, A. J.; Burrows, H. D. Binding of divalent and higher valent metal ions to surfactants and polyelectrolytes. Current Opinion in Colloid & Interface Science 2017, 32, 76–83. doi:10.1016/j.cocis.2017.10.003
  • Birch, D.; Christensen, M. V.; Staerk, D.; Franzyk, H.; Nielsen, H. M. Fluorophore labeling of a cell-penetrating peptide induces differential effects on its cellular distribution and affects cell viability. Biochimica et biophysica acta. Biomembranes 2017, 1859, 2483–2494. doi:10.1016/j.bbamem.2017.09.015
  • Wong, J. K.; Proschogo, N.; Todd, M. H.; Rutledge, P. J. Selective Displacement of a Scorpionand Triazole Ligand from Metallocyclam Complexes Visualised with NMR Spectroscopy. European Journal of Inorganic Chemistry 2017, 2017, 1075–1086. doi:10.1002/ejic.201601474
  • Wong, J. K.; Todd, M. H.; Rutledge, P. J. Recent Advances in Macrocyclic Fluorescent Probes for Ion Sensing. Molecules (Basel, Switzerland) 2017, 22, 200. doi:10.3390/molecules22020200
  • Rodríguez, G.; Nargoli, J.; López, A. M.; Moyna, G.; Álvarez, G.; Fernández, M.; Osorio-Martı́nez, C. A.; González, M.; Cerecetto, H. Synthesis and in vivo proof of concept of a BODIPY-based fluorescent probe as a tracer for biodistribution studies of a new anti-Chagas agent. RSC Advances 2017, 7, 7983–7989. doi:10.1039/c6ra27851e
  • Mirri, G.; Schoenmakers, D. C.; Kouwer, P. H. J.; Veranič, P.; Muševič, I.; Štefane, B. Synthesis of Functional Fluorescent BODIPY-based Dyes through Electrophilic Aromatic Substitution: Straightforward Approach towards Customized Fluorescent Probes. ChemistryOpen 2016, 5, 450–454. doi:10.1002/open.201600067

Patents

  • LEE JUN SEOK; DHIRAJ P MURALE; HONG SEONGCHEOL; HONG KYUNG TAEL; KIM YUN KYUNG; LEE SEOK. NIR fluorescent probe for imaging of mitochondria. KR 20200015119 A, Feb 12, 2020.
Other Beilstein-Institut Open Science Activities