Facile Decoration of Functionalized Single-Wall Carbon Nanotubes with Phthalocyanines via “Click Chemistry”

• Published in: Journal of the American Chemical Society Vol. 130; no. 34; pp. 11503 - 11509
• Main Authors: Campidelli, Stéphane, Ballesteros, Beatriz, Filoramo, Arianna, Díaz, David Díaz, de la Torre, Gema, Torres, Tomás, Rahman, G. M. Aminur, Ehli, Christian, Kiessling, Daniel, Werner, Fabian, Sgobba, Vito, Guldi, Dirk M, Cioffi, Carla, Prato, Maurizio, Bourgoin, Jean-Philippe
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 27.08.2008; Amer Chemical Soc
• Subjects: Biocompatible Materials - chemical synthesis; Chemistry; Chemistry, Multidisciplinary; Indoles - chemistry; Materials Testing; Microscopy, Atomic Force; Microscopy, Electron, Transmission; Nanotechnology - methods; Nanotubes, Carbon - chemistry; Organometallic Compounds - chemistry; Photochemistry; Physical Sciences; Science & Technology; Spectrum Analysis, Raman; Surface Properties; POLYMERS; ELECTRON INJECTION; TRANSPORTERS; CYCLOADDITIONS; STABILIZATION
• ISSN: 0002-7863; 1520-5126
• DOI: 10.1021/ja8033262

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.