Facile decoration of functionalized single-wall carbon nanotubes with phthalocyanines via "Click Chemistry"

被引:244
作者
Campidelli, Stephane [1 ]
Ballesteros, Beatriz [2 ]
Filoramo, Arianna [1 ]
Diaz Diaz, David [2 ]
de la Torre, Gema [2 ]
Torres, Tomas [2 ]
Rahman, G. M. Aminur [3 ,4 ]
Ehli, Christian [3 ,4 ]
Kiessling, Daniel [3 ,4 ]
Werner, Fabian [3 ,4 ]
Sgobba, Vito [3 ,4 ]
Guldi, Dirk M. [3 ,4 ]
Cioffi, Carla [5 ]
Prato, Maurizio [5 ]
Bourgoin, Jean-Philippe [1 ]
机构
[1] CEA Saclay, CNRS, URA 2464, Lab Elect Mol,DSM IRAMIS SPEC, F-91191 Gif Sur Yvette, France
[2] Univ Autonoma Madrid, Dept Quim Organ, E-28049 Madrid, Spain
[3] Univ Erlangen Nurnberg, Dept Chem & Pharm, D-91058 Erlangen, Germany
[4] Univ Erlangen Nurnberg, Interdisciplinary Ctr Mol Mat, D-91058 Erlangen, Germany
[5] Univ Trieste, Dipartimento Sci Farmaceut, Unit Trieste, INSTM, I-34127 Trieste, Italy
关键词
D O I
10.1021/ja8033262
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We describe the functionalization of single-wall carbon nanotubes (SWNTs) with 4-(2-trimethylsilyl)ethynylaniline and the subsequent attachment of a zinc-phthalocyanine (ZnPc) derivative using the reliable Huisgen 1,3-dipolar cycloaddition. The motivation of this study was the preparation of a nanotube-based platform which allows the facile fabrication of more complex functional nanometer-scale structures, such as a SWNT-ZnPc hybrid. The nanotube derivatives described here were fully characterized by a combination of analytical techniques such as Raman, absorption and emission spectroscopy, atomic force and scanning electron microscopy (AFM and SEM), and thermogravimetric analysis (TGA). The SWNT-ZnPc nanoconjugate was also investigated with a series of steady-state and time-resolved spectroscopy experiments, and a photoinduced communication between the two photoactive components (i.e., SWNT and ZnPc) was identified. Such beneficial features lead to monochromatic internal photoconversion efficiencies of 17.3% when the SWNT-ZnPc hybrid material was tested as photoactive material in an ITO photoanode.
引用
收藏
页码:11503 / 11509
页数:7
相关论文
共 66 条
  • [1] Ago H, 1999, ADV MATER, V11, P1281, DOI 10.1002/(SICI)1521-4095(199910)11:15<1281::AID-ADMA1281>3.0.CO
  • [2] 2-6
  • [3] Highly functionalized carbon nanotubes using in situ generated diazonium compounds
    Bahr, JL
    Tour, JM
    [J]. CHEMISTRY OF MATERIALS, 2001, 13 (11) : 3823 - +
  • [4] Baibarac M, 2006, J NANOSCI NANOTECHNO, V6, P289, DOI 10.1166/jnn.2006.002
  • [5] Synthesis, characterization and photophysical properties of a SWNT-phthalocyanine hybrid
    Ballesteros, Beatriz
    Campidelli, Stephane
    de la Torre, Gema
    Ehli, Christian
    Guldi, Dirk M.
    Prato, Maurizio
    Torres, Tomas
    [J]. CHEMICAL COMMUNICATIONS, 2007, (28) : 2950 - 2952
  • [6] Single-wall carbon nanotubes bearing covalently linked phthalocyanines -: photoinduced electron transfer
    Ballesteros, Beatriz
    de la Torre, Gema
    Ehli, Christian
    Rahman, G. M. Aminur
    Agullo-Rueda, F.
    Guldi, Dirk M.
    Torres, Tomas
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (16) : 5061 - 5068
  • [7] Observation of electroluminescence and photovoltaic response in ionic junctions
    Bernards, Daniel A.
    Flores-Torres, Samuel
    Abruna, Hector D.
    Malliaras, George G.
    [J]. SCIENCE, 2006, 313 (5792) : 1416 - 1419
  • [8] Photovoltaic properties of dye functionalized single-wall carbon nanotube/conjugated polymer devices
    Bhattacharyya, S
    Kymakis, E
    Amaratunga, GAJ
    [J]. CHEMISTRY OF MATERIALS, 2004, 16 (23) : 4819 - 4823
  • [9] Biomedical applications of functionalised carbon nanotubes
    Bianco, A
    Kostarelos, K
    Partidos, CD
    Prato, M
    [J]. CHEMICAL COMMUNICATIONS, 2005, (05) : 571 - 577
  • [10] CuI-catalyzed alkyne-azide "click" cycloadditions from a mechanistic and synthetic perspective
    Bock, VD
    Hiemstra, H
    van Maarseveen, JH
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (01) : 51 - 68