Fullerene derivatives, method of synthesizing them and their use

Details Fullerene derivatives, method of synthesizing them and their use Fullerene derivatives, method of synthesizing them and their use

1995-02-15

1996-12-24

Datlow, Philip I.

Organic compounds -- part of the class 532-570 series

Organic compounds

Unsubstituted hydrocarbyl chain between the ring and the -c-...

540556, 544338, 252500, C07D24138, C07D24310, C07D24504, C07D48706

Patent

active

055874762

DESCRIPTION:

BRIEF SUMMARY
This is a national stage application under 35USC 371 of international application Pct/EP93/02306 filed Aug. 26, 1993.


FIELD OF THE INVENTION

The invention relates to new addition compounds of diamines with fullerenes C.sub.60 and/or C.sub.70 and also a process for their preparation and their use.


BACKGROUND OF THE INVENTION

Since the discovery of fullerenes, a third modification of carbon, and particularly since their preparation has been possible, work has been carried out worldwide with an increasing tendency toward their chemical modification. This is particularly true of the most stable fullerene molecule C.sub.60 which is also the one most readily obtainable in workable amounts (L. F. Lindoy, Nature, Vol. 357, 443 (1992); R. M. Baum, Chemical a. Engineering News 1991, Vol. 69, No. 50, p. 17).
Besides a series of different chemical reactions on the fullerene C.sub.60, the addition of amines to the C.sub.60 molecule has also already been reported [F. Wudl et al. in "Fullerenes: Synthesis, Properties and Chemistry of Large Carbon Clusters, Edit. G. S. Hammond and V. J. Kuck, ACS Symposium-Series, 481; Washington, D.C., 1992, p. 161; R. Seshadri, A. Govindaraj, R. Nagarajan, T. Pradeep and C. N. R. Rao, Tetrahedron Letters 33, No. 15, 2069 (1992)]. C.sub.60 is a polyfunctional molecule. A significant disadvantage in the reported reactions is the formation of complex mixtures, which cannot be separated by conventional methods, in the reaction of the polyfunctional C.sub.60 with amines. In almost every case, the reactions carried out in the manner reported hitherto give a myriad of different reaction products from which pure individual substances can only be isolated with unjustifiably great effort, if at all [A. Hirsch, Angew. Chem. 104 (1992), 808].
At present there are no known chemical reactions of nucleophiles with fullerenes which, when carried out in a conventional industrial manner, lead directly to uniform compounds or even to monoadducts or for which the subsequent application of conventional separation techniques, such as recrystallization or column chromatography, enables uniform compounds, in particular monoadducts, to be obtained from the mixtures formed. In "Tetrahedron Letters 33, page 2069 (1992)" mention is indeed made, inter alia, of obtaining a virtually pure 1:1 adduct of n-butylamine with C.sub.60, but apart from information about IR and UV absorption bands, no material data are reported and no information is given on the elemental composition based on analytical results and on the isolation of such a fullerene derivative.


SUMMARY OF THE INVENTION

It has now surprisingly been found that the action of diamines, preferably disecondary diamines, on fullerene, forms addition compounds of the diamine with fullerene, among which the monoaddition compound and diaddition compounds represent the main products, which can very easily, using conventional separation methods, be separated and separated from multiple-addition compounds and thus be isolated in pure form.
The invention accordingly provides addition compounds obtainable by reaction of diamines of the formula I, ##STR2## where R.sup.1 is (C.sub.2 -C.sub.4)-alkylene or 1,2- or 1,3-cyclo-(C.sub.3 -C.sub.7)-alkylene and -C.sub.3)-alkyl or fullerene C.sub.60 and/or C.sub.70.


BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 illustrates a graphical representation of an IR spectrum of a monoaddition compound according to one embodiment of the invention.
FIG. 2 illustrates a graphical representation of a Raman spectrum of a monoaddition compound according to one embodiment of the invention.
FIG. 3 is a graphical representation of a UV spectrum of a monoaddition compound according to one embodiment of the invention.
FIG. 4 is a graphical representation of an IR spectrum of an addition compound according to one embodiment of the invention.
FIG. 5 is a graphical representation of a UV spectrum of an addition compound according to one embodiment of the invention.
FIG. 6 is a graphical representation of an IR spectrum of a hydrochloride of a mono

REFERENCES:
Kampe, Angew. Chem., 105(8), (1993), pp. 1203-1205.
Kampe, Angew Chem. Int. Ed. Engl, 32(8), (1993), pp. 1174-1176.
Wudl et al, Chemical Abstract 116:193407h (1992).
Kampe et al, Chem. Abstract 119:270776u (1993).
Haddon, R. C. et al., "Conducting films of C.sub.60 and C.sub.70 by alkali-metal doping" Nature, vol. 350, (1991), pp. 320-322.
Sijbesma, R. et al., "Synthesis of a Fullerene Derivative for the Inhibition of HIV Enzymes" J. Am. Chem. Soc. 1993, vol. 115, pp. 6510-6512.
Suzuki, T. et al., "Dihydrofulleroid H.sub.2 C.sub.61 : Synthesis and Properties of the Parent Fulleroid" J. Am. Chem. Soc. 1992, vol. 114, pp. 7301-7302.
Leonard F. Lindoy, "C.sub.60 Chemistry Expands", Nature, vol. 357, 11 Jun. 1992, pp. 443-444.
Rudy M. Baum, "Systematic Chemistry of C.sub.60 Beginning to Emerge", C&EN San Francisco, Dec. 16, 1991, pp. 17-20.
F. Wudl et al., "Survey of Chemical Reactivity of C.sub.60 Electrophile and Dieno--Polarophile Par Excellence", American Chemical Society, 1992, pp. 161-175.
Ram Seshadri et al., "Addition of Amines and Halogens to Fullerenes C.sub.60 and C.sub.70 ", Tetrahedron Letters, vol. 33, No. 15, 1992, pp. 2069-2070.
Andreas Hirsh et al., "Titration of C.sub.60 : A method For the Synthesis of Organofullerenes", Angew. Chem. Int. Ed. Engl., 31 (1992) No. 6, pp. 766-768 (English) and 808-10 (German).

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