Metal-organic frameworks with exceptionally large pore aperatures

Patent metadata

Field	Value
Publication number	US-9669098-B2
Application number	US-201514797312-A
Country	US
Kind code	B2
Filing date	Jul 13, 2015
Priority date	Oct 13, 2011
Publication date	Jun 6, 2017
Grant date	Jun 6, 2017

Abstract

The disclosure relates to metal organic frameworks or isoreticular metal organic frameworks, methods of production thereof, and methods of use thereof.

First claim

What is claimed is:

1. A composition comprising a pharmaceutically active agent and a MOF or IRMOF comprising the general structure M-L-M, wherein M comprises a metal and L is a linking moiety of Formula I:

wherein,
A 1 -A 8 are independently either N or C;
X 1 and X 2 are functional groups (FG);
R 1 -R 12 are independently selected from the group comprising H, FG, (C 1 -C 12 )alkyl, substituted (C 1 -C 12 )alkyl, (C 1 -C 12 )alkenyl, substituted (C 1 -C 12 )alkenyl, (C 1 -C 12 )alkynyl, substituted (C 1 -C 12 )alkynyl, hetero-(C 1 -C 12 )alkyl, substituted hetero-(C 1 -C 12 )alkyl, hetero-(C 1 -C 12 )alkenyl, substituted hetero-(C 1 -C 12 )alkenyl, hetero-(C 1 -C 12 )alkynyl, substituted hetero-(C 1 -C 12 )alkynyl, (C 1 -C 12 )cycloalkyl, substituted (C 1 -C 12 )cycloalkyl, aryl, substituted aryl, heterocycle, substituted heterocycle, —C(R 13 ) 3 , —CH(R 13 ) 2 , —CH 2 R 13 , —C(R 13 ) 3 , —CH(R 14 ) 2 , —CH 2 R 14 , —OC(R 13 ) 3 , —OCH(R 13 ) 2 , —OCH 2 R 14 , —OC(R 14 ) 3 , —OCH(R 14 ) 2 , —OCH 2 (R 14 ),

wherein R 1 and R 2 are linked together to form a substituted or unsubstituted ring selected from the group comprising cycloalkyl, aryl and heterocycle, and wherein R 3 and R 4 are linked together to form a substituted or unsubstituted ring selected from the group comprising cycloalkyl, aryl and heterocycle;
R 13 is selected from the group comprising FG, (C 1 -C 12 )alkyl, (C 1 -C 12 )substituted alkyl, (C 1 -C 12 )alkenyl, substituted (C 1 -C 12 )alkenyl, (C 1 -C 12 )alkynyl, substituted (C 1 -C 12 )alkynyl, hetero-(C 1 -C 12 )alkyl, substituted hetero-(C 1 -C 12 )alkyl, hetero-(C 1 -C 12 )alkenyl, substituted hetero-(C 1 -C 12 )alkenyl, hetero-(C 1 -C 12 )alkynyl, substituted hetero-(C 1 -C 12 )alkynyl, hemiacetal, hemiketal, acetal, ketal, and orthoester;
R 14 is one or more substituted or unsubstituted rings selected from the group comprising cycloalkyl, aryl, and heterocycle;
y is a number from 0 to 3;
z is a number from 0 to 20; and
with the proviso that R is absent when bound to an A that is N; and
wherein the pharmaceutically active agent is located with pores of the MOF or IRMOF.

2. The composition of claim 1 , wherein M is either a transition metal or an alkaline earth metal.

3. The composition of claim 1 , wherein M is either Mg or Zn.

4. The composition of claim 3 , wherein X 1 and X 2 are carboxylic acids.

5. The composition of claim 4 , wherein A 1 -A 8 are C.

6. The composition of claim 5 , wherein
R 1 and R 10 are hydroxyls;
R 2 -R 5 , R 7 , R 9 , R 11 and R 12 are hydrogen; and
R 6 and R 8 are selected from the group consisting of (C 1 -C 12 )alkyl, (C 1 -C 12 )alkenyl, substituted (C 1 -C 12 )alkenyl, (C 1 -C 12 )alkynyl, substituted (C 1 -C 12 )alkynyl, hetero-(C 1 -C 12 )alkyl, substituted hetero-(C 1 -C 12 )alkyl, hetero-(C 1 -C 12 )alkenyl, substituted hetero-(C 1 -C 12 )alkenyl, hetero-(C 1 -C 12 )alkynyl, and substituted hetero-(C 1 -C 12 )alkynyl.

7. The composition of claim 6 , wherein
R 6 and R 8 are (C 1 -C 6 )alkyls.

8. The composition of claim 7 , wherein z is a number from 1 to 15.

9. The composition of claim 1 , wherein the MOF or IRMOF further comprises a post-framework reactant.

10. The composition of claim 9 , wherein the post-framework reactant decreases the hydrophobicity of the framework.

11. The composition of claim 1 , wherein at least one linking moiety comprises Formula I(a):

12. A composition comprising a pharmaceutically active agent and a MOF or IRMOF having the general structure M-L-M, wherein the pharmaceutically active agent is present in pores of the MOF or IRMOF, wherein M comprises a metal and L is a linking moiety, and wherein at least one linking moiety comprises Formula IV(a):

13. A composition comprising a pharmaceutically active agent and a MOF or IRMOF having the general structure M-L-M, wherein the pharmaceutically active agent is present in pores of the MOF or IRMOF, wherein M comprises a metal and L is a linking moiety, and wherein at least one linking moiety comprises Formula IV(b):

wherein, y is a number from 0 to 20.

14. The composition of claim 1 , wherein the pharmaceutically active agent is selected from the group consisting of a protein, a drug and a gas.

15. The composition of claim 12 , wherein the pharmaceutically active agent is selected from the group consisting of a protein, a drug and a gas.

16. The composition of claim 13 , wherein the pharmaceutically active agent is selected from the group consisting of a protein, a drug and a gas.

Assignees

• Univ California

Inventors

• Yaghi Omar M
• Furukawa Hiroyasu
• Deng Hexiang

Classifications

• B01J20/0225

  Compounds of Fe, Ru, Os, Co, Rh, Ir, Ni, Pd, Pt · CPC title

• B01J20/28076

  being more than 1.0 ml/g · CPC title

• A61K47/24 Primary

  containing atoms other than carbon, hydrogen, oxygen, halogen, nitrogen or sulfur, e.g. cyclomethicone or phospholipids · CPC title

• B01D53/02

  by adsorption, e.g. preparative gas chromatography {(solid sorbent compositions B01J20/00, preparation of inorganic compounds or elements C01)} · CPC title

• C02F1/285

  using synthetic organic sorbents · CPC title