Functionalization of Carbon Nanotubes and Synthesis - DiVA Portal

64 Pages·2011·3.39 MB·English

List of papers
This thesis is based on the following papers, which are referred to in the text
by their Roman numerals.
I Reproducibility and Efficiency of Carbon Nanotube End-
Group Generation and Functionalization, Claes-Henrik An-
dersson, Helena Grennberg, Eur. J. Org. Chem., 2009, 4421–
4428.
II Reagent-free Microwave-assisted Purification of Carbon
Nanotubes, Khalil Chajara, Claes-Henrik Andersson, Jun Lu,
Erika Widenkvist, Helena Grennberg, New J. Chem., 2010, 34,
2275–2280.
III Reversible Non-Covalent Derivatisation of Carbon Nano-
tubes with Glycosides, Claes-Henrik Andersson, Martina
Lahmann, Stefan Oscarson, Helena Grennberg, Soft Matter,
2009, 5, 2713–2716.
IV Synthesis and IR Spectroelectrochemical Studies of a
[60]Fulleropyrrolidine-(tricarbonyl)chromium Complex:
Probing C Redox States by IR Spectroscopy, Claes-Henrik
60
Andersson, Gustav Berggren, Sascha Ott, Helena Grennberg,
Eur. J. Inorg. Chem. 2011, 1744–1749.

V Synthesis and characterization of a ferrocene-linked bis-
fullerene[60] dumbbell, Claes-Henrik Andersson, Leif Ny-
holm, Helena Grennberg, submitted.

VI Short ferrocene-[60]fulleropyrrolidine oligomers. A prelim-
inary account on synthetic studies, Claes-Henrik Andersson,
Helena Grennberg, preliminary manuscript.

VII Appendix

Contribution report
The author wishes to clarify his contribution to the papers I-VII in the thesis
I Carried out all experimental work and contributed in writing the
paper.
II Significantly contributed to the experimental work and charac-
terizations of the purified single- and multi walled carbon nano-
tubes. Contributed in writing the paper.
III Performed all experimental work except synthesizing the glyco-
sides 3 and 4. Wrote a major part of the paper
IV Synthesized and characterized all compounds, contributed in the
electrochemical characterizations and contributed significantly
in writing the paper.
V Synthesized and characterized all compounds, contributed in the
electrochemical characterizations and contributed significantly
in writing the paper.
VI Carried out all experimental work and wrote the manuscript.
VII Carried out all experimental work.

Contents

1. Introduction .......................................................................................................................... 11
1.1 Fullerene C ................................................................................................................ 12
60
1.2 Carbon nanotubes ......................................................................................................... 15
1.3 Production of fullerenes and carbon nanotubes ........................................................... 18
1.4 Characterization of carbon nanotubes .......................................................................... 19
1.5 Examples of applications for fullerene C and carbon nanotubes ............................... 23
60
2. Purification of carbon nanotubes (paper I & II) ................................................................... 25
2.1 Acid-mediated purification of CNTs (paper I) ............................................................. 25
2.2 A fast, reagent-free purification of CNTs (paper II) .................................................... 25
2.2.1 Purification of HiPCo SWNTs ............................................................................ 26
2.2.2 Purification of MWNTs ....................................................................................... 27
2.3 Conclusion .................................................................................................................... 29
3. Reversible non-covalent derivatization of CNTs with glycosides (paper III) ..................... 30
3.1 Introduction .................................................................................................................. 30
3.2 Synthesis of pyrene derivatives .................................................................................... 31
3.3 Formation and characterization of glycosylated carbon nanotubes ............................. 32
3.3 Discussion and conclusion ........................................................................................... 34
4. Towards fullerene based molecular wires (papers IV-VI) ................................................... 35
4.1 Introduction .................................................................................................................. 35
4.2 A [60]fulleropyrrolidine-Cr(CO) complex of type D (Paper IV) ............................... 37
3
4.3 Type F [60]fulleropyrrolidine dumbbells ..................................................................... 41
4.3.1 Attempts towards a fulleropyrrolidine-Cr(CO) dumbbell (appendix VII) ......... 42
3
4.3.2 A ferrocene based fulleropyrrolidine dumbbell (Paper V) .................................. 44
4.4 Preliminary synthetic results on fulleropyrrolidine-ferrocene oligomers (Paper VI) ... 50
4.5 Conclusions .................................................................................................................. 53
5. Concluding remarks ............................................................................................................. 55
6. Svensk sammanfattning ....................................................................................................... 56
7. Acknowledgements .............................................................................................................. 58
8. References ............................................................................................................................ 60

Abbreviations
Ac Acyl
Bu Butyl
BuLi Butyl lithium
CNT Carbon nanotube
DCC N, N´-dicyclohexylcarbodiimide
DCM Dichloromethane
DIPA Diisopropylamine
DMAP 4-Dimethylaminopyridine
DMF N,N-dimethylformamide
Et O Diethyl ether
2
EtOH Ethanol
Fc Ferrocene
FT-IR Fourier transform infrared spectroscopy
HiPCo High pressure carbon monoxide
HOBt 1-Hydroxybenzotriazole
HPLC High performance liquid chromatography
IR Infrared spectroscopy
LED-PGSE Longitudinal eddy current delay pulsed gradient spin echo
Maldi-TOF Matrix assisted laser desorption ionization-time of flight
Me Methyl
MeOH Methanol
MiW Microwave
MWNT Multi walled carbon nanotube
nm Nanometer
NMR Nuclear magnetic resonance
ODCB ortho-dichlorobenzene
RBM Radial breathing mode
RT Room temperature
SEM Scanning electron microscopy
STM Scanning tunneling microscopy
SWNT Single walled carbon nanotube
TEM Transmission electron microscopy
TGA Thermo gravimetric analysis
THF Tetrahydrofuran
TMEDA Tetramethyleneethylenediamine
UV/Vis Ultra violet/visible