US 6,162,926 AGranted

Multi-substituted fullerenes and methods for their preparation and characterization

AssigneeSphere Biosystems, Inc.

InventorsRandall B. Murphy, Stephen R. Wilson, Quing Lu

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Abstract

The invention is directed to multiply-substituted fullerene derivatives of novel configurations, and methods for their preparation and use. The methods involve the combinatorial synthesis of a library of fullerene derivatives and comprises the steps of forming a mixture of fullerene derivatives by reacting the C.sub.n fullerene with two or more reactive precursor compounds, and removing the unreacted compounds to yield the fullerene derivatives having the desired activity. Methods for the identification and screening of a combinatorial library of fullerenes by .sup.3 He-nuclear magnetic resonance and electrospray mass spectrometry to define members with the optimal desired activity are also provided.

Claims12

Dependent claims

A multiply-substituted fullerene compound having the structure:

##STR40## wherein:
Z.sub.1, Z.sub.2 and Z.sub.3 are absent or present, provided that at least one is present, and are independently selected from the group consisting of --NR.sub.1 --, --O--CR.sub.1 R.sub.2 --, --S--CR.sub.1 R.sub.2 --, --NR.sub.1 --CR.sub.2 R.sub.3 --, --R.sub.1 R.sub.2 C--NR.sub.3 --NR.sub.4 --, --R.sub.1 R.sub.2 C--NR.sub.3 --O--, --N.dbd.NR.sub.1 --, --N.dbd.N--NR.sub.1 --, --N.dbd.N--CR.sub.1 R.sub.2 --, --O--NR.sub.1 --O--, --R.sub.1 R.sub.2 C--O--CR.sub.3 R.sub.4 --, --R.sub.1 R.sub.2 C--O--NR.sub.3 --, --R.sub.1 C.dbd.N--O--, --R.sub.1 N--NR.sub.2 --NR.sub.3 --, --R.sub.1 N--NR.sub.2 --O--, --CR.sub.1 R.sub.2 --CR.sub.3 .dbd.CR.sub.4 --, --CR.sub.1 R.sub.2 --CR.sub.4 R.sub.4 --CR.sub.5 CR.sub.6 --CR.sub.7 R.sub.8 --, --CR.sub.1 R.sub.2 --CR.sub.3 .dbd.CR.sub.4 --CR.sub.5 R.sub.6 --, --CR.sub.1 .dbd.CR.sub.2 --CR.sub.3 .dbd.CR.sub.4 -- and --CR.sub.1 R.sub.2 --CR.sub.3 .dbd.C.dbd.CR.sub.4 -- such that Z.sub.1, Z.sub.2 and Z.sub.3 are each attached to the carbon skeleton of the fullerene structure by two single bonds selected from the group consisting of a carbon-carbon bond, a carbon-oxygen bond, a carbon-sulfur bond and a carbon-nitrogen bond, the unsatisfied valences of each Z moiety being the location of those bonds;
R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7 and R.sub.8 are the same or different and are selected from the group consisting of hydrogen, oxygen, lower alkyl, higher alkyl, cycloalkyl, alkenyl, alkynyl, alkoxy, carboxylic acids, carboxylic esters, alkylthio, thioalkyl, aryl, aryloxy, aralkyl, primary amine, secondary amine, amino acid side chains, and heterocycles, such that C together with any two R groups bonded thereto forms an oxo or thioxo group, hydrocarbon ring or heterocycle;
Y.sub.1 and Y.sub.2 are absent or present, provided that at least one is present, and are selected from the group consisting of hydrogen, lower alkyl, higher alkyl, cycloalkyl, alkenyl, alkynyl, alkoxy, alkylthio, thioalkyl, aryl, aryloxy, arylkyl, primary amine, secondary amine, amino acid side chains, and heterocycles;
20<n<240;
(k.sub.1 +k.sub.2) is 1 to n;
and
(m.sub.1 +m.sub.2 +m.sub.3) is 1 to n/2, with the limitation that 2(m.sub.1 +m.sub.2 +m.sub.3)+(k.sub.1 +k.sub.2)<n;
or a salt or addition compound thereof.

6 more elements

A multiply-substituted fullerene compound having the structure:

##STR41## wherein:
Z.sub.4, Z.sub.5 and Z.sub.6 are absent or present, provided that at least two are present, and are independently selected from the group consisting of --NR.sub.9 --, --O--CR.sub.9 R.sub.10 --, --S--CR.sub.9 R.sub.10 --, --NR.sub.9 --CR.sub.10 R.sub.11 --, --R.sub.9 R.sub.10 C--NR.sub.11 --NR.sub.12 --, --R.sub.9 R.sub.10 C--NR.sub.11 --O--, --N.dbd.NR.sub.9 --, --N.dbd.N--NR.sub.9 --, --N.dbd.N--CR.sub.9 R.sub.10 --, --O--NR.sub.9 --O--, --R.sub.9 R.sub.10 C--O--CR.sub.11 R.sub.12 --, --R.sub.9 R.sub.10 C--O--NR.sub.11 --, --R.sub.9 C.dbd.N--O--, --R.sub.9 N--NR.sub.10 --NR.sub.11 --, --R.sub.9 N--NR.sub.10 --O--, --CR.sub.9 R.sub.10 --CR.sub.11 .dbd.CR.sub.12 --, --CR.sub.9 R.sub.10 --CR.sub.11 R.sub.12 --CR.sub.13 CR.sub.14 --CR.sub.15 R.sub.16 --, --CR.sub.9 .dbd.R.sub.10 --CR.sub.11 R.sub.12 --CR.sub.13 R.sub.14 --, --CR.sub.9 .dbd.CR.sub.10 --CR.sub.11 .dbd.CR.sub.12 -- and --CR.sub.9 R.sub.10 --CR.sub.11 .dbd.C.dbd.CR.sub.12 --, such that Z.sub.4, Z.sub.5 and Z.sub.6 are each attached to the carbon skeleton of the fullerene structure by two single bonds selected from the group consisting of a carbon-carbon bond, a carbon-oxygen bond, a carbon-sulfur bond and a carbon-nitrogen bond, the unsatisfied valences of each Z moiety being the location of those bonds;
R.sub.9, R.sub.10, R.sub.11, R.sub.12, R.sub.13, R.sub.14, R.sub.15 and R.sub.16 are the same or different and are selected from the group consisting of hydrogen, oxygen, lower alkyl, higher alkyl, cycloalkyl, alkenyl, alkynyl, alkoxy, carboxylic acids, carboxylic esters, alkylthio, thioalkyl, aryl, aryloxy, aralkyl, primary amine, secondary amine, amino acid side chains, and heterocycles, such that C together with any two R groups bonded thereto forms an oxo or thioxo group, hydrocarbon ring or heterocycle;
20<n<240;
and
(m.sub.4 +m.sub.5 +m.sub.6) is 2 to n/2;
or a salt or addition compound thereof.

4 more elements

Dependencies are inferred from the claim text.

Facts

Application: 08/969,261Filed 13 Nov 1997 · continuation
Priority: 31 Jul 1995
Granted: 19 Dec 2000
Term ends: Not estimatedThe source records don’t support an estimate.

Classification24 codes

G11C 13/025
Using elements whose operation depends upon chemical change: using fullerenes, e.g. C60, or nanotubes, e.g. carbon or silicon nanotubes
B82Y 10/00
Nanotechnology for information processing, storage or transmission
C07D 209/58
Ring systems containing three or more rings: [b]- or [c]-condensed
C07D 213/16
Containing only hydrogen and carbon atoms in addition to the ring nitrogen atom: containing only one pyridine ring