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Tables of Contents for Lecture Notes on Fullerene Chemistry
Chapter/Section Title
Page #
Page Count
Preface
xiii
Introduction
1
16
Occurrence
1
1
The Carbon Allotropes
2
2
Discovery of the Fullerenes
4
4
Isolation and Characterisation of the Fullerenes
8
3
Endohedral Fullerenes (Incar-fullerenes)
11
1
Multiwall or Nested Fullerenes
12
1
Opened Fullerenes
13
1
Elongated Fullerenes --- Nanotubes
13
1
Heterofullerenes
14
3
The Structure and Properties of Fullerenes
17
25
Symmetry and Schlegel Diagrams
17
2
Higher Fullerenes
19
1
Preparation of Fullerenes
19
2
Nomenclature of Fullerenes
21
5
Quasi-fullerenes
26
1
Dimeric and Fused Fullerenes
26
1
Properties of Fullerenes
27
5
Bond Lengths
27
1
Solubility
28
1
Thermodynamic and Related Properties
29
1
Oxidation and Reduction: Voltammetry
30
1
Spectroscopic Properties
31
1
The Structure and Properties of Nanotubes
32
10
Addition Patterns
42
14
Introduction
42
3
Addends with No 1,2-Eclipsing Interactions
45
2
Addends with Small Eclipsing Interactions
47
2
Addends with Larger Steric Interactions
49
3
1,2- vs. 5,6-Addition to [70]Fullerene
52
1
Addition to Higher Fullerenes
53
3
Hydrogenation
56
15
Hydrogenation Conditions
56
3
Hydrogenation with Hydrogen under Pressure
56
1
Hydrogenation with Hydrogen and a Catalyst
57
1
Dissolving Metal Reductions
57
1
Di-Imide Reduction
58
1
Reduction Using Organometallic Reagents
58
1
Transfer Hydrogenation
58
1
Products of Hydrogenation
59
8
Dihydrofullerenes
60
1
C60H2
60
1
C70H2
60
1
Tetrahydrofullerenes
61
2
C60H6
63
1
C60H18
64
1
C60H36
64
1
C70H8/10/12
65
1
C70H36/38/40
66
1
Hydrogenated Higher Fullerenes
66
1
Formation of Methylene Adducts
66
1
Theoretical Calculations
67
4
C60H2 and C70H2
67
1
C60H4
67
1
C60H6
67
1
C60H36
68
3
Reduction by Electron Addition, and Reaction of Fullerene Radical Anions with Electrophilies
71
9
Formation of Radical Anions
71
2
Reduction by Metals
73
1
Reduction by Organic Donors
74
1
Electrocrystallisation
74
1
Electrochemical Reduction
75
1
Reaction of Electrophiles with Radical Anions
75
1
Reaction of Fullerenes with Alkali- and Alkaline Earth Metals
76
4
Nucleophilic Addition, and Reaction of Fullerene Anions with Electrophiles
80
11
Reaction with Neutral Nucleophiles
80
4
Anions Formed by Addition of a Negatively Charged Nucleophile
84
1
Reactions of Anions with Electrophiles
85
3
Anions Formed by Proton Loss
88
3
Radical Reactions
91
23
Halogenation
91
13
Fluorination
92
1
Fluorination with Fluorine Gas
92
5
Fluorination with Metal Fluorides
97
1
Fluorination with Krypton Difluoride
98
1
Properties of Fluorofullerenes
99
1
Clorination
99
2
Bromination
101
2
Iodination
103
1
Reactions with Other Radicals
104
10
Radical Reactions of [60]fullerene
104
5
Radical Reactions of [70]fullerene
109
5
Nucleophilic Substitution of Fullerenes: Fullerenes as Electrophiles
114
23
Methoxydehalogenation
115
1
Fullerenol Formation
115
7
Hydroxydenitration and Hydroxydesulphonation
115
1
Use of Aqueous HNO3/H2SO4
116
1
Use of Nitronium Tetrafluoroborate
117
1
Use of Oleum
118
3
Fullerenols from Nitrofullerenes
121
1
Fullerenol Formation from Halogenofullerenes
121
1
Fullerenol Formation via Hydroboration
122
1
Fullerenol Formation Involving Reaction with Oxygen
122
1
Biological Applications of Fullerenols
122
1
Polymers Derived from Fullerenols
123
1
Allyldechlorination
123
1
Aryldehalogenation
123
10
Substitutions in C60Cl6
124
5
Substitutions in C70Cl10
129
2
Substitutions in C60F18
131
2
Substitutions in Bromo[60]fullerenes
133
1
Fullerenylation
133
4
Cycloadditions
137
63
[1 + 2] Cycloadditions: Reactions That Produce Methano- and Homofullerenes and Their Homologues
137
26
Addition of Carbon
138
1
Additions Involving Carbenes, and Azo Precursors
138
9
Formation of Methanofullerenes Through the Use of Ylides
147
1
Formation of Methanofullerenes by α-Halocarbanion Addition
147
2
Miscellaneous Reactions Which Produce Methanofullerenes
149
1
Polyaddition and Tether-Directed Reactions
150
5
Addition of Nitrogen: Formation of Azahomofullerene and Epiminofullerenes
155
5
Addition of Oxygen: Formation of Epoxides
160
2
Addition of Silicon: Formation of Fullerene Siliranes
162
1
[2 + 2] Cycloadditions
163
4
Additions by Alkenes
163
2
Additions Involving Pseudo Alkenes (4-Membered Rings etc.)
165
1
Addition of Benzyne
166
1
[3 + 2] Cycloadditions
167
9
Formation of Cyclopentafullerenes
167
2
Formation of Pyrrolidinofullerenes
169
3
Formation of Pyrrolo[60]fullerenes
172
1
Formation of Pyrazolo[60]fullerene
172
1
Formation of Isoxazolofullerenes
173
1
Formation of Oxazolo[60]fullerene
174
1
Formation of an Isothiazolo[60]fullerene
174
1
Formation of a Thiazolo[60]fullerene
175
1
Formation of Furano[60]fullerenes
175
1
Formation of Disolanofullerenes
176
1
[4 + 2] Cycloadditions: Diels-Alder Reactions
176
10
Reactions of o-Quinodimethane and Derivatives
177
3
Reactions of Cyclobutane Derivatives
180
1
Additions of Buta-1,3-Diene Derivatives
180
3
Addition of Anthracene
183
1
Addition of Cyclopentadiene, Furan and Derivatives
184
2
[6 + 2] Reactions
186
1
[8 + 2] Reactions
186
14
Oxidation and the Formation of Radical Cations and Cations
200
6
Addition of Oxygen
200
1
Formation of Radical Cations
201
2
Formation of Cations
203
3
Inorganic and Organometallic Derivatives of Fullerenes
206
17
Introduction
206
1
Osmylation
206
3
Fullerene Complexes of Iridium, Rhodium and Cobalt
209
5
Fullerene Complexes of Platinum, Palladium and Nickel
214
2
Fullerene Complexes of Iron and Ruthenium
216
1
Fullerene Complexes of Molybdenum, Vanadium and Tantalum
217
1
Miscelaneous Fullerene-Metal Complexes
217
6
Polymers, Dendrimers, Dimers, Dumb-bells and Related Structures
223
28
`Pearl-Necklace' Polymers
223
6
Directly-Linked Fullerenes
223
4
Indirectly-Linked Fullerenes
227
2
`Pendant-Chain' Polymers
229
7
Attachment of a Fullerene to a Preformed Polymer Chain
230
4
Polymers Formed from Addended Fullerenes
234
1
Star Polymers
235
1
Electroactive Polymers
236
1
Fullerenes as Polymer Dopants
237
1
Dendrimers
238
1
Dimers
239
1
Dumb-Bells
240
4
Ball and Chain Structures
244
7
Heterofullerenes
251
6
Borafullerenes
252
1
Azafullerenes
252
5
The Chemistry of Incar-fullerene (Endohedral Fullerenes)
257
1
Nomenclature
257
1
Fullerenes with Incarcerated Metals
257
2
Properties
259
2
Chemistry
261
1
Fullerenes with Incarcerated Nitrogen
262
1
Fullerenes Having Incarcerated Noble Gases
262