Facile and environmentally friendly halogenation of BODIPYs in deep eutectic solvent

Dyes and Pigments

Volumn 112, Issue , 2015, Pages 274-279

  Wang, Liang ^a   Zhu, Kai Qiang ^a   Chen, Qun ^a   He, Ming Yang ^a  

^a CHANGZHOU UNIVERSITY   (China)

Author keywords

Boron dipyrromethene; Deep eutectic solvent; Fluorescent dye; Green chemistry; Halogenation; Hexafluoroisopropanol

Indexed keywords

CHLORINE COMPOUNDS; DIES;

BORON DIPYRROMETHENE; DEEP EUTECTIC SOLVENTS; FLUORESCENT DYES; GREEN CHEMISTRY; HEXAFLUOROISOPROPANOL;

HALOGENATION;

EID: 84907366330     PISSN: 01437208     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dyepig.2014.07.024     Document Type: Article

References (27)

1. G. Ulrich, R. Ziessel, and A. Harriman The chemistry of fluorescent bodipy dyes: versatility unsurpassed Angew Chem Int Ed 47 2008 1184 1201
2. N. Boens, V. Leen, and W. Dehaen Fluorescent indicators based on BODIPY Chem Soc Rev 41 2012 1130
3. V. Leen, P. Yuan, L. Wang, N. Boens, and W. Dehaen Synthesis of meso-halogenated BODIPYs and access to meso-substituted analogues Org Lett 14 2012 6150 6153
4. W. Li, W. Zhang, X. Dong, L. Yan, R. Qi, and W. Wang et al. Porous heterogeneous organic photocatalyst prepared by HIPE polymerization for oxidation of sulfides under visible light J Mater Chem 22 2012 17445 17448
5. A. Kamkaew, and K. Burgess Double-targeting using a TrkC ligand conjugated to dipyrrometheneboron difluoride (BODIPY) based photodynamic therapy (PDT) agent J Med Chem 56 2013 7608 7614
6. A. Vázquez-Romero, N. Kielland, M.J. Arévalo, S. Preciado, R.J. Mellanby, and Y. Feng et al. Multicomponent reactions for de Novo synthesis of BODIPY probes: in vivo imaging of phagocytic macrophages J Am Chem Soc 135 2013 16018 16021
7. M. Baruah, W. Qin, R.A.L. Vallée, D. Beljonne, T. Rohand, and W. Dehaen et al. A highly potassium-selective ratiometric fluorescent indicator based on BODIPY azacrown ether excitable with visible light Org Lett 7 2005 4377 4380 (Pubitemid 41439668)
8. T. Rohand, M. Baruah, W. Qin, N. Boens, and W. Dehaen Functionalisation of fluorescent BODIPY dyes by nucleophilic substitution Chem Commun 2006 266 268
9. V. Leen, E. Braeken, K. Luckermans, C. Jackers, M. Van derAuweraer, and N. Boens et al. A versatile, modular synthesis of monofunctionalized BODIPY dyes Chem Commun 2009 4515 4517
10. V. Leen, T. Leemans, N. Boens, and W. Dehaen 2- and 3-Monohalogenated BODIPY dyes and their functionalized analogues: synthesis and spectroscopy Eur J Org Chem 2011 4386 4396
11. T. Yogo, Y. Urano, Y. Ishitsuka, F. Maniwa, and T. Nagano Highly efficient and photostable photosensitizer based on BODIPY chromophore J Am Chem Soc 127 2005 12162 12163 (Pubitemid 41279207)
12. S. Atilgan, Z. Ekmekci, A.L. Dogan, D. Guc, and E.U. Akkaya Water soluble distyryl-boradiazaindacenes as efficient photosensitizers for photodynamic therapy Chem Commun 2006 4398 4400 (Pubitemid 44611702)
13. N. Adarsh, M. Shanmugasundaram, R.R. Avirah, and D. Ramaiah Aza-BODIPY derivatives: enhanced quantum yields of triplet excited states and the generation of singlet oxygen and their role as facile sustainable photooxygenation catalysts Chem Eur J 18 2012 12655 12662
14. C. Zhang, J. Zhao, S. Wu, Z. Wang, W. Wu, and J. Ma et al. Intramolecular RET enhanced visible light-absorbing Bodipy organic triplet photosensitizers and application in photooxidation and triplet-triplet annihilation upconversion J Am Chem Soc 135 2013 10566 10578
15. L. Huang, J. Zhao, S. Guo, C. Zhang, and J. Ma Bodipy derivatives as organic triplet photosensitizers for aerobic photoorganocatalytic oxidative coupling of amines and photooxidation of dihydroxylnaphthalenes J Org Chem 78 2013 5627 5637
16. L. Bonardi, G. Ulrich, and R. Ziessel Tailoring the properties of poron-dipyrromethene dyes with acetylenic functions at the 2,6,8 and 4-B substitution positions Org Lett 10 2008 2183 2186
17. J. Goday, G. Vives, and J.M. Tour Synthesis of highly fluorescent BODIPY-based nanocars Org Lett 12 2010 1464 1467
18. J.H. Ye, G. Wang, C. Huang, Z. Hu, W. Zhang, and Y. Zhang An efficient and convenient bromination of BODIPY derivatives with copper(II) bromide Synthesis 44 2012 104 110
19. A.P. Abbott, R.C. Harris, K. Ryder, C.D. Agostino, L. Gladden, and M.D. Mantle Glycerol eutectics as sustainable solvent systems Green Chem 13 2011 82 90
20. C. Ru, and B. Knig Low melting mixtures in organic synthesis-an alternative to ionic liquids? Green Chem 14 2012 2969 2982
21. Q. Zhang, K. De Oliveira Vigier, S. Royer, and F. Jéròme Deep eutectic solvents: syntheses, properties and applications Chem Soc Rev 41 2012 7108 7146
22. Y. Gu, and F. Jéròme Bio-based solvents: an emerging generation of fluids for the design of eco-efficient processes in catalysis and organic chemistry Chem Soc Rev 42 2013 9550 9570
23. S. Khaksar, and S.M. Talesh Transition metal-free oxidation of activated alcohols to aldehydes and ketones in 1,1,1,3,3,3-hexafluoro-2-propanol J Fluor Chem 140 2012 95 98
24. S. Khaksar, and S.M. Talesh A simple, efficient and green procedure for the synthesis of bis-indolyl methanes in 1,1,1,3,3,3-hexafluoro-2-propanol J Fluor Chem 135 2012 87 90
25. M.O. Ratnikov, V.V. Tumanov, and V.A. Smit Lewis acid catalyst free electrophilic alkylation of silicon-capped π donors in 1,1,1,3,3,3- hexafluoro-2-propanol Angew Chem Int Ed 47 2008 9739 9742
26. T. Dohi, A. Maruyama, Y. Minamitsuji, N. Takenaga, and Y. Kita First hypervalent iodine(III)-catalyzed C-N bond forming reaction: catalytic spirocyclization of amides to N-fused spirolactams Chem Commun 2007 1224 1226 (Pubitemid 46412134)
27. J. Ye, Z. Hu, Y. Wang, W. Zhang, and Y. Zhang A new practical and highly efficient iodination of BODIPY derivatives with hypervalent iodine reagent Tetrahedron Lett 53 2012 6858 6860