Synthesis of cyclophanes from a self-assembly reaction
AssigneeUniversity of Oregon
InventorsDarren W. Johnson, Mary Collins
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Abstract
Disclosed herein is a novel method for preparing cyclophanes, comprising forming a disulfide cyclophane by contacting a linker moiety which includes two or more thiol groups, with a metal salt and an oxidant. The disulfide cyclophane is then desulfurized to form a thiacyclophane comprising thioether bridges. This thiacyclophane optionally may be further desulfurized to form an unsaturated hydrocarbon cyclophane, which can then be reduced to form a saturated hydrocarbon cyclophane. The various cyclophanes can be synthesized in a ring form, such as a dimer, trimer or tetramer etc., or they can be synthesized in a tetrahedral or larger structure. Also disclosed are novel cyclophanes formed by the disclosed method.
Claims16
A compound, having a formula
- wherein:
- ring 1 is aryl or heteroaryl;
- each R independently is carboxyl ester, aminocarbonyl, aliphatic, heteroaliphatic, NO2, sulfonyl, amine, protected amine, aryl, heteroaryl, OH, oxo or halogen;
- m independently is from 0 to 4;
- p is from 1 to 10;
- each L independently is aliphatic, aralkyl, aryl, heteroaryl or heteroaralkyl;
- and
- if the compound has formula I, ring 1 is 1,4-disubstituted phenyl, m is 0 and each L is CH2, then p is not 1, 2 or 3;
- if the compound has formula I, ring 1 is 1,3-disubstituted phenyl, m is 0 and each L is CH2, then p is not 1;
- and
- if the compound has formula I, ring 1 is 1,5-naphthyl, m is 0 and each L is CH2, then p is not 1.
A compound selected from
Dependencies are inferred from the claim text.