Fullerenes from aromatic precursors by surface-catalysed cyclodehydrogenation

被引:257
作者
Otero, Gonzalo [1 ]
Biddau, Giulio [2 ]
Sanchez-Sanchez, Carlos [1 ]
Caillard, Renaud [1 ]
Lopez, Maria F. [1 ]
Rogero, Celia [3 ]
Palomares, F. Javier [1 ]
Cabello, Noemi [4 ]
Basanta, Miguel A. [2 ]
Ortega, Jose [2 ]
Mendez, Javier [1 ]
Echavarren, Antonio M. [4 ]
Perez, Ruben [2 ]
Gomez-Lor, Berta [1 ]
Martin-Gago, Jose A. [1 ,3 ]
机构
[1] CSIC, Inst Ciencia Mat, Madrid 28049, Spain
[2] Univ Autonoma Madrid, Dept Fis Teor Mat Condensada, E-28049 Madrid, Spain
[3] CSIC INTA, Ctr Astrobiol, Madrid 28850, Spain
[4] Inst Chem Res Catalonia ICIQ, Tarragona 43007, Spain
关键词
D O I
10.1038/nature07193
中图分类号
O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];
学科分类号
07 ; 0710 ; 09 ;
摘要
Graphite vaporization provides an uncontrolled yet efficient means of producing fullerene molecules. However, some fullerene derivatives or unusual fullerene species might only be accessible through rational and controlled synthesis methods. Recently, such an approach has been used(1) to produce isolable amounts of the fullerene C-60 from commercially available starting materials. But the overall process required 11 steps to generate a suitable polycyclic aromatic precursor molecule, which was then dehydrogenated in the gas phase with a yield of only about one per cent. Here we report the formation of C-60 and the triazafullerene C57N3 from aromatic precursors using a highly efficient surface-catalysed cyclodehydrogenation process. We find that after deposition onto a platinum (111) surface and heating to 750 K, the precursors are transformed into the corresponding fullerene and triazafullerene molecules with about 100 per cent yield. We expect that this approach will allow the production of a range of other fullerenes and heterofullerenes(2,3), once suitable precursors are available. Also, if the process is carried out in an atmosphere containing guest species, it might even allow the encapsulation of atoms or small molecules to form endohedral fullerenes(4,5).
引用
收藏
页码:865 / U19
页数:5
相关论文
共 22 条
[1]   X-ray-diffraction characterization of Pt(111) surface nanopatterning induced by C60 adsorption [J].
Felici, R ;
Pedio, M ;
Borgatti, F ;
Iannotta, S ;
Capozi, M ;
Ciullo, G ;
Stierle, A .
NATURE MATERIALS, 2005, 4 (09) :688-692
[2]   VARIATION OF SURFACE-REACTION PROBABILITY WITH REACTANT ANGLE OF INCIDENCE - MOLECULAR-BEAM STUDY OF ASYMMETRY OF STEPPED PLATINUM CRYSTAL-SURFACES FOR H-H BOND BREAKING [J].
GALE, RJ ;
SALMERON, M ;
SOMORJAI, GA .
PHYSICAL REVIEW LETTERS, 1977, 38 (18) :1027-1029
[3]   Synthesis of a triaza analogue of crushed-fullerene by intramolecular palladium-catalyzed arylation [J].
Gómez-Lor, B ;
Echavarren, AM .
ORGANIC LETTERS, 2004, 6 (17) :2993-2996
[4]   Zipping up 'the crushed fullerene' C60H30:: C60 by fifteen-fold, consecutive intramolecular H2 losses [J].
Gómez-Lor, B ;
Koper, C ;
Fokkens, RH ;
Vlietstra, EJ ;
Cleij, TJ ;
Jenneskens, LW ;
Nibbering, NMM ;
Echavarren, AM .
CHEMICAL COMMUNICATIONS, 2002, (04) :370-371
[5]   Synthesis of 'crushed fullerene' C60H30 [J].
Gómez-Lor, B ;
de Frutos, O ;
Echavarren, AM .
CHEMICAL COMMUNICATIONS, 1999, (23) :2431-2432
[6]   Electronic structure of carbon nitride thin films studied by X-ray spectroscopy techniques [J].
Hellgren, N ;
Guo, JH ;
Luo, Y ;
Såthe, C ;
Agui, A ;
Kashtanov, S ;
Nordgren, J ;
Ågren, H ;
Sundgren, JE .
THIN SOLID FILMS, 2005, 471 (1-2) :19-34
[7]   ISOLATION OF THE HETEROFULLERENE C59N AS ITS DIMER (C59N)(2) [J].
HUMMELEN, JC ;
KNIGHT, B ;
PAVLOVICH, J ;
GONZALEZ, R ;
WUDL, F .
SCIENCE, 1995, 269 (5230) :1554-1556
[8]   Carbon monoxide inside an open-cage fullerene [J].
Iwamatsu, Sho-ichi ;
Stanisky, Christopher M. ;
Cross, R. James ;
Saunders, Martin ;
Mizorogi, Naomi ;
Nagase, Shigeru ;
Murata, Shizuaki .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (32) :5337-5340
[9]   Multicenter approach to the exchange-correlation interactions in ab initio tight-binding methods -: art. no. 235101 [J].
Jelínek, P ;
Wang, H ;
Lewis, JP ;
Sankey, OF ;
Ortega, J .
PHYSICAL REVIEW B, 2005, 71 (23)
[10]   Encapsulation of molecular hydrogen in fullerene C 60 by organic synthesis [J].
Komatsu, K ;
Murata, M ;
Murata, Y .
SCIENCE, 2005, 307 (5707) :238-240