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Maindashchain polymers with incorporated [60]fullerene units are accessible by reaction of buckminsterfullerene with functionalized bis-o-quinodimethanes. Cross linking can be effectively suppressed by carefully directed admixing of a mono-o-quinodimethane. The polymer 11(n) of high molecular weight and excellent solubility, consisting of 80 [60]fullerene units on the average, is affordable. This polymer can be processed to thin amorphous films of high quality by spin coating.

Diels-Alder reaction of 4-amino-o-quinodimethane (6) with [60]fullerene (1) affords the thermally stable and chemically reactive adduct 7(n). The nucleophilic amino group of 7(n) is well suited for the covalent attachment of different molecules to the [60]fullerene core by further chemical reactions.

The synthesis of the first fullerene cryptate 7 with a sodium ion bound to a benzo[2.2.2]cryptand covalently attached to a methanofullerene[60] is described. The amphiphilic properties of 7 as well as of a variety of other covalent fullerene derivatives with polar functional groups and the ability of these compounds to form Langmuir monolayers at the air-water interface were investigated in a systematic study. Among these derivatives are Diels-Alder adducts of C-60 and methanofullerenes, four of which are fullerene C-glycosides. The films at the water surface were characterized by their surface pressure versus molecular area isotherms, compression and expansion cycles, and optical light microscopy. UV/Vis spectroscopy and small-angle X-ray diffraction (SAXS) were employed for LB film characterization on solid substrates. Parameters influencing the spreading and monolayer character include a) polarity, b) balance of hydrophobicity to hydrophilicity, c) size and bulkiness of the polar groups attached to the fullerene, and d) presence of aromatic residues in these groups.

The Diels-Alder reaction of o-quinodimethanes to buckminsterfullerene C-60 (1) affords thermally stable derivatives. 4-Carboxy-o-quinodimethane (4)was prepared in situ from 3,4-bis(bromomethyl)benzoic acid (3) and reacted with 1 to give the carboxy-substituted adduct mixture 5(n). Due to its decreased solubility, 5(rt) was used without further purification for transformations into the corresponding esters and amines. This was achieved by two different methods: (a) via the carboxylic acid chloride 6(n), whereby the alcohol/amine has to be used in excess, and (2) via the active ester 7(n = 1), which allows stoichiometric reactions with amines. All these derivatives are quite Soluble in commonly used organic solvents. This enabled us to separate and completly characterize the products.

α-Substttulcd o-quinodimethanes facihtate the covlcnt attachment of many attractive molecules in closest proximity to the C60-core Thermal isomcrizalion of various (±)-hydroxyben/ocyclobutenc esters 4. 8. 10 and 13 in the presence of C60 provided the corresponding fullerene adducts 5(n). 7(n). 9(n). 11(n) and 12(n) in high yields Using a dumbbell shaped bis-o-quinodimethane precursor 19. accessible from (±)-7-hydroxybenzocyclobutcne and dodccancdicarboxyhc acid dichloride. a soluble C60-contaimng polymer 20 was formed