Cyclopropenium polymers and methods for making the same
AssigneeThe Trustees of Columbia University in the City of New York
InventorsTristan Hayes Lambert, Luis M Campos, Jeffrey Bandar, Emma Jane Dell
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Abstract
The present invention provides, inter alia, a process for incorporating a cyclopropenium ion into a polymeric system. Processes for making cross-linked polymers, linear polymers, and dendritic polymers, as well as for incorporating a cyclopropenium ion onto a preformed polymer are also provided. Further provided are stable, polycationic compounds, various polymers that contain stable cyclopropenium cations, and substrates containing such polymers. The use of these polymers in water purification systems, antimicrobial coatings, ion-transport membranes, cell supports, drug delivery vehicles, and gene therapeutic vectors are also provided.
Claims45
A process for incorporating a cyclopropenium ion into a polymeric system comprising contacting a functionalized cyclopropenium ion with a functionalized compound capable of reacting with the functional group of the cyclopropenium ion for a period of time and under conditions suitable for the functionalized cyclopropenium and the functionalized compound to react and form a polymeric system that comprises a stable cyclopropenium cation that remains positively charged;
- wherein the functionalized cyclopropenium ion is a compound of formula (100):
- wherein
- X1-3 are independently selected from the group consisting of Cl and N;
- and
- R1-4 are independently selected from the group consisting of no atom, amino, aryl, heteroaryl,C1-10alkoxy, C2-10alkenyloxy, C2-10alkynyloxy, C1-10alkyl C3-10cycloalkyl, C2-10alkenyl, C3-10cycloalkenyl, C2-10alkynyl, halogen, aryloxy, heteroaryloxy, C2-10alkoxycarbonyl, C1-10alkenylthio, C2-10alkynylthio, C2-10alkynylthio, C1-10alkylsulfonyl, C1-10alkylsulfinyl, aryl-C1-10alkyl, heteroaryl-C1-10alkyl, aryl-C1-10heteroalkyl, heteroaryl-C1-10heteroalkyl, a phosphorus group, a silicon group and a boron group, wherein R1 and R2 or R3 and R4 are optionally combined to form a 5 to 8-membered carbocyclic or heterocyclic ring;
- further wherein the aliphatic or aromatic portions of R1 and R2 are optionally substituted with from 1 to 4 substituents selected from the group consisting of halogen, cyano, nitro, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, aryl, C1-6alkoxy, C2-6alkenyloxy, C2-6alkynyloxy,aryloxy, C2-6alkoxycarbonyl, C1-6alkylthio, C1-6alkylsulfonyl, C1-6alkylsulfinyl, oxo, imino, thiono, primary amino, carboxyl, C1-6alkylamino, C1-6dialkylamino, amido, nitrogen heterocycles, hydroxy, thiol and phosphorus.
A process for making a cross-linked polymer comprising contacting an alkene functionalized cyclopropenium ion with a polymer comprising a pendant thiol group, for a period of time and under conditions suitable for the functionalized cyclopropenium ion and the polymer to react and form a cross-linked polymer that comprises a stable cyclopropenium cation that remains positively charged.
A process for making a cross-linked polymer comprising contacting a thiol functionalized cyclopropenium ion with a functionalized compound comprising an alkene group, for a period of time and under conditions suitable for the functionalized cyclopropenium ion and the functionalized compound to react and form a cross-linked polymer that comprises a stable cyclopropenium cation that remains positively charged.
A process for making a linear polymer comprising contacting a functionalized cyclopropenium ion with a polymerizing agent for a period of time and under conditions suitable for the functionalized cyclopropenium ion to react and to form a linear polymer that comprises a stable cyclopropenium cation that remains positively charged.
A process for incorporating a cyclopropenium ion onto a preformed polymer comprising contacting a cyclopropenium ion functionalized to participate in a click reaction with a preformed polymer backbone having a pendant group that is functionalized with a complementary group suitable for participating in a click reaction with the cyclopropenium ion for a period of time and under conditions suitable for the functionalized cyclopropenium ion and the preformed polymer to react via a click chemistry mechanism and form a polymer that comprises a stable cyclopropenium cation that remains positively charged.
Dependencies are inferred from the claim text.