Conductive open frameworks

Patent metadata

Field	Value
Publication number	US-9978474-B2
Application number	US-201615050136-A
Country	US
Kind code	B2
Filing date	Feb 22, 2016
Priority date	Sep 27, 2010
Publication date	May 22, 2018
Grant date	May 22, 2018

Abstract

The disclosure relates generally to materials that comprise conductive covalent organic frameworks. The disclosure also relates to materials that are useful to store and separate gas molecules and sensors.

First claim

What is claimed is:

1. A conductive covalent-organic framework (COF) comprising:
a plurality of cores, wherein each core forms at least one imine bond to at least one linking moiety; and
wherein at least one core of the plurality of cores comprises a conductive core moiety and/or wherein at least one linking moiety comprises a conductive linking moiety and wherein the core has a structure of Formula I:

wherein:
R 1 -R 4 are independently selected from the group consisting of H, D, FG, (C 1 -C 20 )alkyl, substituted (C 1 -C 20 )alkyl, (C 1 -C 20 )alkenyl, substituted (C 1 -C 20 )alkenyl, (C 1 -C 20 )alkynyl, substituted (C 1 -C 20 )alkynyl, hetero-(C 1 -C 20 )alkyl, substituted hetero-(C 1 -C 20 )alkyl, hetero-(C 1 -C 20 )alkenyl, substituted hetero-(C 1 -C 20 )alkenyl, hetero-(C 1 -C 20 )alkynyl, substituted hetero-(C 1 -C 20 )alkynyl, (C 1 -C 20 )cycloalkyl, substituted (C 1 -C 20 )cycloalkyl, aryl, substituted aryl, heterocycle, and substituted heterocycle;
R 5 and R 6 are independently selected from the group consisting of H, D, FG, (C 1 -C 20 )alkyl, substituted (C 1 -C 20 )alkyl, (C 1 -C 20 )alkenyl, substituted (C 1 -C 20 )alkenyl, (C 1 -C 20 )alkynyl, substituted (C 1 -C 20 )alkynyl, hetero-(C 1 -C 20 )alkyl, substituted hetero-(C 1 -C 20 )alkyl, hetero-(C 1 -C 20 )alkenyl, substituted hetero-(C 1 -C 20 )alkenyl, hetero-(C 1 -C 20 )alkynyl, substituted hetero-(C 1 -C 20 )alkynyl, (C 1 -C 20 )cycloalkyl, substituted (C 1 -C 20 )cycloalkyl, aryl, substituted aryl, heterocycle, and substituted heterocycle, or are linked together to form a substituted or unsubstituted ring selected from the group consisting of cycloalkyl, aryl and heterocycle;
R 7 and R 8 are independently selected from the group consisting of H, D, FG, (C 1 -C 20 )alkyl, substituted (C 1 -C 20 )alkyl, (C 1 -C 20 )alkenyl, substituted (C 1 -C 20 )alkenyl, (C 1 -C 20 )alkynyl, substituted (C 1 -C 20 )alkynyl, hetero-(C 1 -C 20 )alkyl, substituted hetero-(C 1 -C 20 )alkyl, hetero-(C 1 -C 20 )alkenyl, substituted hetero-(C 1 -C 20 )alkenyl, hetero-(C 1 -C 20 )alkynyl, substituted hetero-(C 1 -C 20 )alkenyl, (C 1 -C 20 )cycloalkyl, substituted (C 1 -C 20 )cycloalkyl, aryl, substituted aryl, heterocycle, and substituted heterocycle, or are linked together to form a substituted or unsubstituted ring selected from the group consisting of cycloalkyl, aryl and heterocycle;
R 9 and R 10 are independently selected from the group consisting of H, D, FG, (C 1 -C 20 )alkyl, substituted (C 1 -C 20 )alkyl, (C 1 -C 20 )alkenyl, substituted (C 1 -C 20 )alkenyl, (C 1 -C 20 )alkynyl, substituted (C 1 -C 20 )alkynyl, hetero-(C 1 -C 20 )alkyl, substituted hetero-(C 1 -C 20 )alkyl, hetero-(C 1 -C 20 )alkenyl, substituted hetero-(C 1 -C 20 )alkenyl, hetero-(C 1 -C 20 )alkynyl, substituted hetero-(C 1 -C 20 )alkenyl, (C 1 -C 20 )cycloalkyl, substituted (C 1 -C 20 )cycloalkyl, aryl, substituted aryl, heterocycle, and substituted heterocycle, or are linked together to form a substituted or unsubstituted ring selected from the group consisting of cycloalkyl, aryl and heterocycle;
R 11 and R 12 are independently selected from the group consisting of H, D, FG, (C 1 -C 20 )alkyl, substituted (C 1 -C 20 )alkyl, (C 1 -C 20 )alkenyl, substituted (C 1 -C 20 )alkenyl, (C 1 -C 20 )alkynyl, substituted (C 1 -C 20 )alkynyl, hetero-(C 1 -C 20 )alkyl, substituted hetero-(C 1 -C 20 )alkyl, hetero-(C 1 -C 20 )alkenyl, substituted hetero-(C 1 -C 20 )alkenyl, hetero-(C 1 -C 20 )alkynyl, substituted hetero-(C 1 -C 20 )alkenyl, (C 1 -C 20 )cycloalkyl, substituted (C 1 -C 20 )cycloalkyl, aryl, substituted aryl, heterocycle, and substituted heterocycle, or are linked together to form a substituted or unsubstituted ring selected from the group consisting of cycloalkyl, aryl and heterocycle;
X 1 -X 8 are independently selected from the group consisting of carbon, oxygen, sulfur, silicon, phosphorous, and nitrogen;
Y 1 -Y 4 are independently selected from H, D, FG, or are absent;
with the proviso that any of R 1 , R 2 , R 3 , or R 4 are absent if bound to an X that is an N.

2. The conductive COF of claim 1 , wherein the one or more cores has a structure of Formula I:

wherein,
R 1 -R 4 are independently selected from the group consisting of H, D, FG, (C 1 -C 6 )alkyl, substituted (C 1 -C 6 )alkyl, (C 1 -C 6 )alkenyl, substituted (C 1 -C 6 )alkenyl, (C 1 -C 6 )alkynyl, substituted (C 1 -C 6 )alkynyl, hetero-(C 1 -C 6 )alkyl, substituted hetero-(C 1 -C 6 )alkyl, hetero-(C 1 -C 6 )alkenyl, substituted hetero-(C 1 -C 6 )alkenyl, hetero-(C 1 -C 6 )alkynyl, substituted hetero-(C 1 -C 6 )alkynyl, (C 1 -C 6 )cycloalkyl, substituted (C 1 -C 6 )cycloalkyl, aryl, substituted aryl, heterocycle, and substituted heterocycle;
R 5 and R 6 are independently selected from the group consisting of H, D, FG, (C 1 -C 6 )alkyl, substituted (C 1 -C 6 )alkyl, (C 1 -C 6 )alkenyl, substituted (C 1 -C 6 )alkenyl, (C 1 -C 6 )alkynyl, substituted (C 1 -C 6 )alkynyl, hetero-(C 1 -C 6 )alkyl, substituted hetero-(C 1 -C 6 )alkyl, hetero-(C 1 -C 6 )alkenyl, substituted hetero-(C 1 -C 6 )alkenyl, hetero-(C 1 -C 6 )alkynyl, substituted hetero-(C 1 -C 6 )alkynyl, (C 1 -C 6 )cycloalkyl, substituted (C 1 -C 6 )cycloalkyl, aryl, substituted aryl, heterocycle, and substituted heterocycle, or are linked together to form a substituted or unsubstituted ring selected from the group consisting of cycloalkyl, aryl and heterocycle;
R 7 and R 8 are independently selected from the group consisting of H, D, FG, (C 1 -C 6 )alkyl, substituted (C 1 -C 6 )alkyl, (C 1 -C 6 )alkenyl, substituted (C 1 -C 6 )alkenyl, (C 1 -C 6 )alkynyl, substituted (C 1 -C 6 )alkynyl, hetero-(C 1 -C 6 )alkyl, substituted hetero-(C 1 -C 6 )alkyl, hetero-(C 1 -C 6 )alkenyl, substituted hetero-(C 1 -C 6 )alkenyl, hetero-(C 1 -C 6 )alkynyl, substituted hetero-(C 1 -C 6 )alkynyl, (C 1 -C 6 )cycloalkyl, substituted (C 1 -C 6 )cycloalkyl, aryl, substituted aryl, heterocycle, and substituted heterocycle, or are linked together to form a substituted or unsubstituted ring selected from the group consisting of cycloalkyl, aryl and heterocycle;
R 9 and R 10 are independently selected from the group consisting of H, D, FG, (C 1 -C 6 )alkyl, substituted (C 1 -C 6 )alkyl, (C 1 -C 6 )alkenyl, substituted (C 1 -C 6 )alkenyl, (C 1 -C 6 )alkynyl, substituted (C 1 -C 6 )alkynyl, hetero-(C 1 -C 6 )alkyl, substituted hetero-(C 1 -C 6 )alkyl, hetero-(C 1 -C 6 )alkenyl, substituted hetero-(C 1 -C 6 )alkenyl, hetero-(C 1 -C 6 )alkynyl, substituted hetero-(C 1 -C 6 )alkynyl, (C 1 -C 6 )cycloalkyl, substituted (C 1 -C 6 )cycloalkyl, aryl, substituted aryl, heterocycle, and substituted heterocycle, or are linked together to form a substituted or unsubstituted ring selected from the group consisting of cycloalkyl, aryl and heterocycle;
R 11 and R 12 are independently selected from the group consisting of H, D, FG, (C 1 -C 6 )alkyl, substituted (C 1 -C 6 )alkyl, (C 1 -C 6 )alkenyl, substituted (C 1 -C 6 )alkenyl, (C 1 -C 6 )alkynyl, substituted (C 1 -C 6 )alkynyl, hetero-(C 1 -C 6 )alkyl, substituted hetero-(C 1 -C 6 )alkyl, hetero-(C 1 -C 6 )alkenyl, substituted hetero-(C 1 -C 6 )alkenyl, hetero-(C 1 -C 6 )alkynyl, substituted hetero-(C 1 -C 6 )alkynyl, (C 1 -C 6 )cycloalkyl, substituted (C 1 -C 6 )cycloalkyl, aryl, substituted aryl, heterocycle, and substituted heterocycle, or are linked together to form a substituted or unsubstituted ring selected from the group consisting of cycloalkyl, aryl and heterocycle;
X 1 -X 8 are independently selected from the group consisting of carbon and nitrogen;
Y 1 -Y 4 are independently selected from H, D, FG, or are absent; and
with the proviso that any of R 1 , R 2 , R 3 , or R 4 ar

Assignees

• Univ California

Inventors

• Yaghi Omar M
• Wan Shun
• Doonan Christian J
• Wang Bo
• Deng Hexiang

Classifications

• H01B1/12 Primary

  organic substances {(organic macromolecular compounds or compositions C08)} · CPC title

• B01J20/26

  Synthetic macromolecular compounds · CPC title

• C07F5/04

  Esters of boric acids · CPC title

• Y02E60/324

  Cross-Sectional Technologies · mapped topic

• C07D487/22

  in which the condensed system contains four or more hetero rings · CPC title