Preparation and characterization of multi-cationic BODIPYs and their synthetically versatile precursors

Dyes and Pigments

Volumn 97, Issue 1, 2013, Pages 1-8

  Bartelmess, Juergen ^a   Weare, Walter W ^a  

^a NORTH CAROLINA STATE UNIVERSITY   (United States)

Author keywords

Cationic BODIPY; Cationic boron dipyrromethene; Fluorescence dye; Fluorescence spectroscopy; Modular organic synthesis; Water soluble dye

Indexed keywords

AQUEOUS APPLICATIONS; BORON DIPYRROMETHENE; BUILDING BLOCKES; CATIONIC BODIPY; CHEMICAL SENSING; COORDINATION COMPLEX; FLUORESCENCE PROPERTIES; FUNCTIONALIZATIONS; MESO POSITIONS; MULTI-PURPOSE; ORGANIC SYNTHESIS; POLAR ORGANIC SOLVENTS; SYNTHETIC PROCEDURES; TARGET MOLECULE; WATER-SOLUBLE DYE;

COORDINATION REACTIONS; DIES; FLUORESCENCE; FLUORESCENCE SPECTROSCOPY; FUNCTIONAL MATERIALS; ORGANIC SOLVENTS; PHOTODYNAMIC THERAPY; TRICHLOROETHYLENE;

DYES;

EID: 84871378578     PISSN: 01437208     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dyepig.2012.11.017     Document Type: Article

References (54)

1. S. Erten-Ela, M.D. Yilmaz, B. Icli, Y. Dede, S. Icli, and E.U. Akkaya A panchromatic boradiazaindacene (BODIPY) sensitizer for dye-sensitized solar cells Org Lett 10 2008 3299 3302
2. Y. Rio, W. Seitz, A. Gouloumis, P. Vázquez, J.L. Sessler, and D.M. Guldi A panchromatic supramolecular fullerene-based donor-acceptor assembly derived from a peripherally substituted BODIPY-zinc phthalocyanine dyad Chem Eur J 16 2010 1929 1940
3. S. Kolemen, O.A. Bozdemir, Y. Cakmak, G. Barin, S. Erten-Ela, and M. Marszalek Optimization of distyryl-Bodipy chromophores for efficient panchromatic sensitization in dye sensitized solar cells Chem Sci 2 2011 949 954
4. S.H. Lim, C. Thivierge, P. Nowak-Sliwinska, J. Han, H. van den Bergh, and G. Wagnières In vitro and in vivo photocytotoxicity of boron dipyrromethene derivatives for photodynamic therapy J Med Chem 53 2010 2865 2874
5. 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
6. T.I. Kim, J. Park, and Y. Kim A gold nanoparticle-based fluorescence turn-on probe for highly sensitive detection of polyamines Chem Eur J 17 2011 11978 11982
7. O.A. Bozdemir, R. Guliyev, O. Buyukcakir, S. Selcuk, S. Koleman, and G. Gulseren Selective manipulation of ICT and pet processes in styryl-bodipy derivatives: applications in molecular logic and fluorescence sensing of metal ions J Am Chem Soc 132 2010 8029 8036
8. S.C. Dodani, Q. He, and C.J. Chang A turn-on fluorescent sensor for detecting nickel in living cells J Am Chem Soc 131 2009 18020 18021
9. J. Bai, and R.E. Pagano Measurement of spontaneous transfer and transbilayer movement of BODIPY-labeled lipids in lipid vesicles Biochem 36 1997 8840 8848
10. S.L. Niu, C. Massif, G. Ulrich, R. Ziessel, P.Y. Renard, and A. Romieu Water-solubilisation and bio-conjugation of a red-emitting BODIPY marker Org Biomol Chem 9 2011 66 69
11. K.P. Armendariz, H.A. Huckabay, P.W. Livanec, and R.C. Dunn Single molecule probes of membrane structure: orientation of BODIPY probes in DPPC as a function of probe structure Analyst 137 2012 1402 1408
12. E. Caruso, S. Banfi, P. Barbieri, B. Leva, and V.T. Orlandi Synthesis and antibacterial activity of novel cationic BODIPY photosensitizers J Photochem Photobiol B 114 2012 44 51
13. T.E. Wood, and A. Thompson Advances in the chemistry of dipyrrins and their complexes Chem Rev 107 2007 1831 1861
14. A. Treibs, and F.H. Kreuzer Difluorboryl-Komplexe von Di- und Tripyrrylmethenen Liebigs Ann Chem 718 1968 208 223
15. G. Ulrich, R. Ziessel, and A. Harriman The chemistry of fluorescent bodipy dyes: versatility unsurpassed Angew Chem Int Ed 47 2008 1184 1201
16. R.W. Wagner, and J.S. Lindsey Boron-dipyrromethene dyes for incorporation in synthetic multi-pigment light-harvesting arrays Pure Appl Chem 68 1996 1373 1380
17. M. Baruah, W. Qin, C. Flors, J. Hofkens, R.A.L. Vallée, and D. Beljonne Solvent and pH dependent fluorescent properties of a dimethylaminostyryl borondipyrromethene dye in solution J Phys Chem A 110 2006 5998 6009
18. J.S. Lee, Kang Ny, Y.K. Kim, A. Samanta, S. Feng, and H.K. Kim Synthesis of a BODIPY library and its application to the development of live cell glucagon imaging probe J Am Chem Soc 131 2009 10077 10082
19. G. Bottari, G. de la Torre, D.M. Guldi, and T. Torres Covalent and noncovalent phthalocyanine-carbon nanostructure systems: synthesis, photoinduced electron transfer, and application to molecular photovoltaics Chem Rev 110 2010 6768 6816
20. C. Ehli, G.M.A. Rahman, N. Jux, D. Balbinot, D.M. Guldi, and F. Paolucci interactions in single wall carbon nanotubes/pyrene/porphyrin nanohybrids J Am Chem Soc 128 2006 11222 11231
21. A.S.D. Sandanayaka, R. Chitta, N.K. Subbaiyan, L. D'Souza, O. Ito, and F. D'Souza Photoinduced charge separation in ion-paired porphyrin-single-wall carbon nanotube donor-acceptor hybrids J Phys Chem C 113 2009 13425 13432
22. Ye Tx, Ye Sl, Dm Chen, Qa Chen, B. Qiu, and X. Chen Spectroscopic characterization of tetracationic porphyrins and their noncovalent functionalization with graphene Spectrochim Acta Part A 86 2012 467 471
23. Y. Jin, L. Xu, W. An, and G. Gao Nanocomposite multilayer films containing Dawson-type polyoxometalate and cationic phthalocyanine: Fabrication, characterization and bifunctional electrocatalytic properties Thin Solid Films 515 2007 5490 5497
24. R. Bonnett Photosensitizers of the porphyrin and phthalocyanine series for photodynamic therapy Chem Soc Rev 24 1995 19 33
25. A.E. O'Connor, W.M. Gallagher, and A.T. Byrne Porphyrin and nonporphyrin photosensitizers in oncology: preclinical and clinical advances in photodynamic therapy Photochem Photobiol 85 2009 1053 1074
26. T.J. Jensen, M.G.H. Vicente, R. Luguya, J. Norton, F.R. Fronczek, and K.M. Smith Effect of overall charge and charge distribution on cellular uptake, distribution and phototoxicity of cationic porphyrins in HEp2 cells J Photochem Photobiol B 100 2010 100 111
27. H. Li, T.J. Jensen, F.R. Fronczek, and M.G.H. Vicente Syntheses and properties of a series of cationic water-soluble phthalocyanines J Med Chem 51 2008 502 511
28. M. Soncin, C. Fabris, A. Busetti, D. Dei, D. Nistri, and G. Roncucci Approaches to selectivity in the Zn(II)-phthalocyanine photosensitized inactivation of wild-type and antibiotic-resistant Staphylococcus aureus Photochem Photobiol Sci 1 2002 815 819
29. E. Reddi, M. Ceccon, G. Valduga, G. Jori, J.C. Bommer, and F. Elisei Photophysical properties and antibacterial activity of meso-substituted cationic porphyrins Photochem Photobiol 75 2002 462 470
30. G. Jori Photodynamic therapy of microbial infections: state of the art and perspectives J Environ Pathol Toxicol Oncol 25 2006 505 519
31. B.L. Carpenter, E. Feese, H. Sadeghifar, D.S. Argyropoulos, and R.A. Ghiladi Porphyrin-cellulose nanocrystals: a photobactericidal material that exhibits broad spectrum antimicrobial activity Photochem Photobiol 88 2012 527 536
32. S.L. Niu, G. Ulrich, R. Ziessel, A. Kiss, P.Y. Renard, and A. Romieu Water-soluble BODIPY derivatives Org Lett 11 2009 2049 2052
33. S.L. Niu, C. Massif, G. Ulrich, P.Y. Renard, A. Romieu, and R. Ziessel Water-soluble red-emitting distyryl-borondipyrromethene (BODIPY) dyes for biolabeling Chem Eur J 18 2012 7229 7242
34. J. Wang, Y. Hou, W. Lei, Q. Zhou, C. Li, and B. Zhang DNA photocleavage by a cationic BODIPY dye through both singlet oxygen and hydroxyl radical: new insight into the photodynamic mechanism of BODIPYs Chem Phys Chem 13 2012 1 10
35. L. Li, J. Han, B. Nguyen, and K. Burgess Syntheses and spectral properties of functionalized, water-soluble BODIPY derivatives J Org Chem 73 2008 1963 1970
36. 2 fluorophores J Org Chem 69 2004 2070 2083
37. A. Harriman, L.J. Mallon, G. Ulrich, and R. Ziessel Rapid intersystem crossing in closely-spaced but orthogonal molecular dyads Chem Phys Chem 8 2007 1207 1214
38. 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
39. K.R. Weishaupt, C.J. Gomer, and T.J. Dougherty Identification of singlet oxygen as the cytotoxic agent in photo-inactivation of a murine tumor Cancer Res 36 1976 2326 2329
40. C. Schweitzer, and R. Schmidt Physical mechanisms of generation and deactivation of singlet oxygen Chem Rev 103 2003 1685 1757
41. M. Alvaro, P. Atienzar, P. de la Cruz, J.L. Delgado, V. Troiani, and H. Garcia Synthesis, photochemistry, and electrochemistry of single-wall carbon nanotubes with pendent pyridyl groups and of their metal complexes with zinc porphyrin. Comparison with pyridyl-bearing fullerenes J Am Chem Soc 128 2006 6626 6635
42. M.V. Martínez-Díaz, G. de la Torre, and T. Torres Lighting porphyrins and phthalocyanines for molecular photovoltaics Chem Commun 46 2010 7090 7108
43. T. Rawling, H. Xiao, S.T. Lee, S.B. Colbran, and A.M. McDonagh Optical and Redox Properties of Ruthenium Phthalocyanine Complexes Tuned with Axial Ligand Substituents Inorg Chem 46 2007 2805 2813
44. V. Artero, M. Chavarot-Kerlidou, and M. Fontecave Splitting water with cobalt Angew Chem Int Ed 50 2011 7238 7266
45. M.L. Kirk, D.A. Shultz, R.D. Schmidt, D. Habel-Rodriguez, H. Lee, and J. Lee Ferromagnetic nanoscale electron correlation promoted by organic spin-dependent delocalization J Am Chem Soc 131 2009 18304 18313
46. M.K. Kahif, J.C. Axelson, N.W. Duffy, C.M. Forsyth, C.J. Chang, and J.R. Long A new direction in dye-sensitized solar cells redox mediator development: in situ fine-tuning of the cobalt(II)/(III) redox potential through lewis base interactions J Am Chem Soc 134 2012 16646 16653
47. T. Lazarides, S. Kuhri, G. Charalambidis, M.K. Panda, D.M. Guldi, and A.G. Coutsolelos Electron vs energy transfer in arrays featuring two bodipy chromophores axially bound to a Sn(IV) porphyrin via a phenolate or benzoate bridge Inorg Chem 51 2012 4193 4204
48. A.B. Pangborn, M.A. Giardello, R.H. Grubbs, R.K. Rosen, and F.J. Timmers Safe and convenient procedure for solvent purification Organometallics 15 1995 1518 1520
49. A.T.R. Williams, S.A. Winfield, and J.N. Miller Relative fluorescence quantum yields using a computer-controlled luminescence spectrometer Analyst 108 1983 1067 1071
50. J. Bartelmess, B. Ballesteros, G. de la Torre, D. Kiessling, S. Campidelli, and M. Prato Phthalocyanine-pyrene conjugates: a powerful approach toward carbon nanotube solar cells J Am Chem Soc 132 2010 16202 16211
51. Y.W. Wang, M. Li, Z. Shen, and X.Z. You Meso-pyridine substituted boron-dipyrromethene (BDP) dye as a ph probe: synthesis, crystal structure and spectroscopic properties Chin J Inorg Chem 24 2008 1247 1252
52. A. Eggenspiller, A. Takai, M.E. El-Khouly, K. Ohkubo, C.P. Gros, and C. Bernhard Synthesis and photodynamics of fluorescent blue BODIPY-porphyrin tweezers linked by triazole rings J Phys Chem A 116 2012 3889 3898
53. Q. Wang, H. Lu, L. Gai, W. Chen, G. Lai, and Z. Li Emission of boron dipyrromethene dyes through energy transfer to their S2 state from polysilane S1 state Dyes Pigm 94 2012 183 186
54. J.Y. Liu, M.E. El-Khouly, S. Fukuzumi, and D.K.P. Ng Photoinduced electron transfer in a distyryl BODIPY-fullerene dyad Chem Asian J 6 2011 174 179 14