Materials and methods for the preparation of anisotropically-ordered solids
View Patent ↗The invention provides materials and methods for making anisotropic solids which may be in the form of films, layers, shaped elements, and other shaped articles. The methods provide anisotropic solids without the need for rolling, rubbing, or stretching to impart orientational alignment of the molecules of the solid. The methods employ organic or organometallic compounds which are soluble orienting molecules. The solvent or solvent system must be sufficiently volatile to be removed without disruption of the molecular orientation. The soluble orienting molecules include those containing one or more hydrophilic and/or ionic groups and the solvent or solvent system can be a polar organic solvent or solvent system or an aqueous solvent or solvent system. The invention also provides novel compounds having quaterrylene, perylene and naphthalene ring systems carrying one or more hydrophilic and/or ionic groups. These novel compounds can exhibit useful absorption and fluorescence properties in solution and in the solid phase and can exhibit useful liquid crystalline properties.
1. A compound of formula:
wherein:
R is a hydrophilic group or a charged group;
C, if present is a suitable counterion or counterions;
q is an integer indicative of the number of X substituents;
each X, independent of other X in the compound, is a non-hydrogen substituent on the aromatic ring system selected from the group consisting of alkyl, alkoxy, alkyl sulfide, alkyl disulfide, cyano, isocyano, thiocyano, isothiocyano, nitro, or halogen, wherein one or more C, CH or CH 2 groups of the alkyl groups or alkoxy groups can be replaced with one or more of an O atom, S atoms, P atoms, a —CO— group, a —O—CO— group, a —SO 3 — group, a —PO 3 — group, an N atom, an NR 1 group, an —NR 1 —CO— group and wherein one or more C of the alkyl or alkoxy group can be substituted with one or more halogens, hydroxyl, thiol, cyano, isocyano, thiocyano, isothiocyano or nitro groups wherein R 1 is an optionally substituted alkyl or aryl group; or a charged substituent, where a charged X is accompanied by an appropriate counterion; and
R″ is hydrogen or a hydrophilic group, which may be a charged group.
2. The compound of claim 1 , wherein R″ is a charged group.
3. The compound of claim 1 , wherein R″ is hydrogen.
4. The compound of claim 1 , wherein R″ is selected from the group consisting of alkoxy, alkyl sulfide, alkyldisulfide, thiol, cyano, isocyano, isothiocyano, nitro, or halogen, wherein one or more C, CH or CH 2 groups of the alkoxy groups can be substituted with one or more halogens, hydroxyl, cyano, isocyano, thiocyano, isothiocyano, or nitro groups.
5. The compound of claim 1 , wherein R″ is a halogen.
6. The compound of claim 1 , wherein R″ is hydroxyl or thiol.
7. The compound of claim 1 , wherein R″ is an amine containing one or more nitrogen atoms.
8. The compound of claim 1 , wherein R″ is a group containing one or more protonated amines or quaternary ammonium groups.
9. The compound of claim 1 , wherein R″ is an amine containing two or more nitrogen atoms.
10. The compound of claim 1 , wherein R and R″ are groups containing one or more protonated amines or quaternary ammonium groups.
11. The compound of claim 1 , wherein R and R″ are amines containing one or more nitrogen atoms.
12. The compound of claim 1 , wherein R is selected from the group consisting of alkyl, alkenyl, alkynyl, or aryl groups substituted with one or more hydrophilic substituents or in which one or more C, CH, CH 2 , or CH 3 moieties are replaced with one or more O atoms, S atoms, P atoms, —CO— groups, —O—CO— groups, —SO 3 — groups, N atoms, —NR 1 groups, or —NR 1 CO— groups, wherein R 1 is an optionally substituted alkyl, alkenyl, alkynyl, or aryl group.
13. The compound of claim 12 , when the one or more hydrophilic substituents are selected from one or more hydroxyls, thiols, alkoxyl groups, —COON groups, or —COOR 2 groups, wherein R 2 is an optionally substituted alkyl, alkenyl, alkynyl, or aryl group.
14. The compound of claim 1 , wherein R is selected from the group consisting of protonated amines, quaternary ammonium ions, and guanidinium ions.
15. The compound of claim 1 , wherein R is negatively charged.
16. The compound of claim 1 , wherein R is positively charged.
17. The compound of claim 1 , wherein R is uncharged.
18. The compound of claim 1 , wherein R″ is an ether group, a polyether group, or an ester group.
19. The compound of claim 1 , wherein R″ is selected from the group consisting of alkyl, alkenyl, alkynyl, or aryl groups substituted with one or more hydrophilic substituents or in which one or more C, CH, CH 2 , or CH 3 moieties are replaced with one or more O atoms, S atoms, P atoms, —CO— groups, —O—CO— groups, —SO 3 — groups, N atoms, —NR 1 groups, or —NR 1 CO— groups, wherein R 1 is an optionally substituted alkyl, alkenyl, alkynyl, or aryl group.
20. The compound of claim 1 , wherein R″ is selected from the group consisting of alkyl, alkenyl, alkynyl, or aryl groups substituted with one or more hydrophilic substituents or in which one or more C, CH, CH 2 , or CH 3 moieties are replaced with one or more O atoms, S atoms, P atoms, —CO— groups, —O—CO— groups, N atoms, —NR 1 groups, or —NR 1 CO— groups, wherein R 1 is an optionally substituted alkyl, alkenyl, alkynyl, or aryl group.