Luminescent Tags on Fullerenes: Eu3+ Complexes with Pendant Fullerenes

Novel fullerene‐containing Eu (III) complexes are obtained by mixing a fullerene derivative bearing chelating pyridinyl groups with an Eu (III) complex possessing three coordinated 4,4,4,‐trifluoro‐1‐(2‐naphtyl)‐1,3‐butanedione residues and two water molecules. One of the complexes designed is formed in water using a water‐soluble fullerene derivative as a precursor material. We investigate the photophysical properties of this new type of highly soluble self‐assembled fullerene‐derivative Eu3+ coordination compounds. A strong emission line of the Eu3+ 4f–4f transition is recorded under excitation with UV irradiation. The behaviour of the complexes in organic matrices and water is studied as the first steps towards luminescence tagged fullerene derivatives for use in biomedicine and optoelectronics.

[1]  Michael R Hamblin,et al.  Photodynamic therapy with fullerenes , 2007, Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology.

[2]  Michael R Hamblin,et al.  Functionalized fullerenes mediate photodynamic killing of cancer cells: Type I versus Type II photochemical mechanism. , 2007, Free radical biology & medicine.

[3]  Yong Cao,et al.  Bright red light-emitting devices based on a novel europium complex doped into polyvinylcarbazole , 2007 .

[4]  V. G. Truong,et al.  Gain properties of an Er3+ complex in a poly(methylmethacrylate) matrix for 1540nm broadband optical amplification , 2007 .

[5]  N. S. Sariciftci,et al.  Photoinduced charge and energy transfer involving fullerene derivatives , 2006, Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology.

[6]  Joseph Zyss,et al.  Demonstration of net gain at 1550nm in an erbium-doped polymersingle mode rib waveguide , 2006 .

[7]  P. Troshin,et al.  Photoaddition of N-substituted piperazines to C60: an efficient approach to the synthesis of water-soluble fullerene derivatives. , 2006, Chemistry.

[8]  R. G. Bulgakov,et al.  Quenching of electronically excited Ln3+* ions by C60 fullerene , 2006 .

[9]  H. Brito,et al.  Synthesis and spectroscopic behavior of highly luminescent Eu(3+)-dibenzoylmethanate (DBM) complexes with sulfoxide ligands. , 2005, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[10]  P. Troshin,et al.  An efficient [2+3] cycloaddition approach to the synthesis of pyridyl- appended fullerene ligands , 2005 .

[11]  S. Bauer,et al.  High-mobility n-channel organic field-effect transistors based on epitaxially grown C60 films , 2005 .

[12]  M. Landthaler,et al.  Photodynamic therapy in dermatology – an update , 2005, Photodermatology, photoimmunology & photomedicine.

[13]  A. Hirsch,et al.  Fullerenes: Chemistry and Reactions , 2005 .

[14]  Niyazi Serdar Sariciftci,et al.  Organic solar cells: An overview , 2004 .

[15]  Edwin Yue-Bun Pun,et al.  Er3+–Yb3+ codoped polymeric optical waveguide amplifiers , 2004 .

[16]  C. Brabec,et al.  Solution‐Processed Organic n‐Type Thin‐Film Transistors , 2003 .

[17]  M. Prato,et al.  Fullerene derivatives: an attractive tool for biological applications. , 2003, European journal of medicinal chemistry.

[18]  E. Stathatos,et al.  Electroluminescence by a Sm3+-diketonate-phenanthroline complex , 2003 .

[19]  Minyung Lee,et al.  Fullerene inhibits β-amyloid peptide aggregation , 2003 .

[20]  L. Ho,et al.  Local carboxyfullerene protects cortical infarction in rat brain , 2002, Neuroscience Research.

[21]  N. S. Sariciftci,et al.  Organic rare earth complexes in polymer matrices and light emitting diodes , 2002 .

[22]  H. Shinohara,et al.  Fullerenes in medicinal chemistry and their biological applications. , 2001, Mini reviews in medicinal chemistry.

[23]  K. O’Malley,et al.  Fullerene-based antioxidants and neurodegenerative disorders. , 2001, Parkinsonism & related disorders.

[24]  C. Teng,et al.  Neuroprotective effect of hexasulfobutylated C60 on rats subjected to focal cerebral ischemia. , 2001, Free radical biology & medicine.

[25]  C. Brabec,et al.  Plastic Solar Cells , 2001 .

[26]  K. Geckeler,et al.  Cyclodextrin–fullerenes: a new class ofwater-soluble fullerenes , 2000 .

[27]  Vojislav I. Srdanov,et al.  Narrow Bandwidth Luminescence from Blends with Energy Transfer from Semiconducting Conjugated Polymers to Europium Complexes , 1999 .

[28]  M. Prato,et al.  Medicinal chemistry with fullerenes and fullerene derivatives , 1999 .

[29]  A. Hirsch,et al.  A highly water-soluble dendro[60]fullerene , 1998 .

[30]  Shen,et al.  Carboxyfullerenes as neuroprotective agents. , 1997, Proceedings of the National Academy of Sciences of the United States of America.

[31]  Y. Ikada,et al.  Antitumor Effect of Poly(Ethylene Glycol)-Modified Fullerene , 1997 .

[32]  T. Yagami,et al.  Acridine Adduct of [60]Fullerene with Enhanced DNA-Cleaving Activity. , 1996, The Journal of organic chemistry.

[33]  D. Schuster,et al.  Biological applications of fullerenes. , 1996, Bioorganic & medicinal chemistry.

[34]  Y. Rubin,et al.  Sequence-specific modification of guanosine in DNA by a C60-linked deoxyoligonucleotide: Evidence for a non-singlet oxygen mechanism , 1996 .

[35]  E. Nakamura,et al.  Fullerene–Oligonucleotide Conjugates: Photoinduced Sequence‐Specific DNA Cleavage , 1995 .

[36]  Roger Taylor,et al.  The chemistry of fullerenes , 1995, Nature.

[37]  Eiichi Nakamura,et al.  Photoinduced biochemical activity of fullerene carboxylic acid , 1993 .

[38]  Fred Wudl,et al.  Inhibition of the HIV-1 protease by fullerene derivatives: model building studies and experimental verification , 1993 .

[39]  A. J. Heeger,et al.  Photoinduced Electron Transfer from a Conducting Polymer to Buckminsterfullerene , 1992, Science.

[40]  F. Wudl The chemical properties of buckminsterfullerene (C60) and the birth and infancy of fulleroids , 1992 .

[41]  Harold W. Kroto C60: BUCKMINSTERFULLERENE, THE CELESTIAL SPHERE THAT FELL TO EARTH , 1992 .

[42]  C. Foote,et al.  Photophysical properties of C70 , 1991 .

[43]  A. Oshiyama,et al.  Cohesive mechanism and energy bands of solid C60. , 1991, Physical review letters.

[44]  Robert L. Whetten,et al.  Photophysical properties of C60 , 1991 .

[45]  W. Krätschmer,et al.  Solid C60: a new form of carbon , 1990, Nature.

[46]  S. C. O'brien,et al.  C60: Buckminsterfullerene , 1985, Nature.

[47]  J. C. Caris,et al.  Synthesis and Fluorescence of Some Trivalent Lanthanide Complexes , 1964 .