Self-assembled nanostructures
View Patent ↗An alkylated benzimidazolone compound of the formula: wherein at least one of R 1 to R 4 is X—R c , where X represents a linking group, and R a , R b , and R c independently represents substituted or unsubstituted alkyl groups, provided that at least one of R a and R b represents H. The present disclosure provides alkylated benzimidazolone compounds and self-assembled nanostructures formed from alkylated benzimidazolone compounds.
1. An alkylated benzimidazolone compound selected from the group consisting of the following compounds:
TABLE 1
Position 5
functional
Sterically Bulky Group(s)
moiety
X
R 1
NH
(CH 2 ) n CH 3 n = 11, 17
NH
NH
NH
X1 = X2 = NH
(CH 2 ) n CH 3 n = 11, 17
X 1 = O X 2 = NH
(CH 2 ) n CH 3 n = 11, 17
N
H
N
H
N
(CH 2 ) n CH 3 n = 3, 11, 17
N
N
N
(CH 2 ) n CH 3 n = 1, 17
N
N
Position 5
functional
Sterically Bulky Group(s)
moiety
R 2
R 3
—
—
—
—
—
—
—
—
—
—
—
—
(CH 2 ) n CH 3 n = 1, 17
—
—
(CH 2 ) n CH 3 n = 3, 11, 17
—
—
—
(CH 2 ) n CH 3 n = 1, 17
(CH 2 ) n CH 3 n = 1, 17
TABLE 2
Group X
R c
and mixtures thereof.
2. A nanostructure comprising molecules of the compound according to claim 1 , non-covalently bound to each other.
3. The nanostructure of claim 2 , wherein the non-covalent bonding is predominately through hydrogen-bonding, aromatic pi-pi interactions, and van der Waals' forces.
4. The nanostructure of claim 2 , wherein the nanostructure is formed by homogeneously mixing the compound with a polar or nonpolar liquid under conditions to effect dissolution and self-assembly of the compound.
5. The nanostructure of claim 2 , wherein the nanostructure is a one-dimensional structure in the form of a nanofibril or nanofiber.
6. The nanostructure of claim 2 , wherein the nanostructure is a two-dimensional structure.
7. The nanostructure of claim 2 , wherein the nanostructure is a three-dimensional structure in the form of a non-covalent gelator network or gel.
8. The nanostructure of claim 2 , wherein the nanostructure has, in at least one dimension, a size ranging from about 1 to about 500 nm, and has a largest dimension of up to about 5000 nm.
9. A marking material composition comprising the nanostructure of claim 2 , wherein the marking material is an ink, a toner, a developer, a paint, or a coating.
10. An organogel composition comprising the nanostructure of claim 2 .