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.
대표청구항▼
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; andwherein at least one core of the plurality of cores comprises a conductive core moiety and/or wherein at least one linking moiety comp
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; andwherein 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: R1-R4 are independently selected from the group consisting of H, D, FG, (C1-C20)alkyl, substituted (C1-C20)alkyl, (C1-C20)alkenyl, substituted (C1-C20)alkenyl, (C1-C20)alkynyl, substituted (C1-C20)alkynyl, hetero-(C1-C20)alkyl, substituted hetero-(C1-C20)alkyl, hetero-(C1-C20)alkenyl, substituted hetero-(C1-C20)alkenyl, hetero-(C1-C20)alkynyl, substituted hetero-(C1-C20)alkynyl, (C1-C20)cycloalkyl, substituted (C1-C20)cycloalkyl, aryl, substituted aryl, heterocycle, and substituted heterocycle;R5 and R6 are independently selected from the group consisting of H, D, FG, (C1-C20)alkyl, substituted (C1-C20)alkyl, (C1-C20)alkenyl, substituted (C1-C20)alkenyl, (C1-C20)alkynyl, substituted (C1-C20)alkynyl, hetero-(C1-C20)alkyl, substituted hetero-(C1-C20)alkyl, hetero-(C1-C20)alkenyl, substituted hetero-(C1-C20)alkenyl, hetero-(C1-C20)alkynyl, substituted hetero-(C1-C20)alkynyl, (C1-C20)cycloalkyl, substituted (C1-C20)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;R7 and R8 are independently selected from the group consisting of H, D, FG, (C1-C20)alkyl, substituted (C1-C20)alkyl, (C1-C20)alkenyl, substituted (C1-C20)alkenyl, (C1-C20)alkynyl, substituted (C1-C20)alkynyl, hetero-(C1-C20)alkyl, substituted hetero-(C1-C20)alkyl, hetero-(C1-C20)alkenyl, substituted hetero-(C1-C20)alkenyl, hetero-(C1-C20)alkynyl, substituted hetero-(C1-C20)alkenyl, (C1-C20)cycloalkyl, substituted (C1-C20)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;R9 and R10 are independently selected from the group consisting of H, D, FG, (C1-C20)alkyl, substituted (C1-C20)alkyl, (C1-C20)alkenyl, substituted (C1-C20)alkenyl, (C1-C20)alkynyl, substituted (C1-C20)alkynyl, hetero-(C1-C20)alkyl, substituted hetero-(C1-C20)alkyl, hetero-(C1-C20)alkenyl, substituted hetero-(C1-C20)alkenyl, hetero-(C1-C20)alkynyl, substituted hetero-(C1-C20)alkenyl, (C1-C20)cycloalkyl, substituted (C1-C20)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;R11 and R12 are independently selected from the group consisting of H, D, FG, (C1-C20)alkyl, substituted (C1-C20)alkyl, (C1-C20)alkenyl, substituted (C1-C20)alkenyl, (C1-C20)alkynyl, substituted (C1-C20)alkynyl, hetero-(C1-C20)alkyl, substituted hetero-(C1-C20)alkyl, hetero-(C1-C20)alkenyl, substituted hetero-(C1-C20)alkenyl, hetero-(C1-C20)alkynyl, substituted hetero-(C1-C20)alkenyl, (C1-C20)cycloalkyl, substituted (C1-C20)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;X1-X8 are independently selected from the group consisting of carbon, oxygen, sulfur, silicon, phosphorous, and nitrogen;Y1-Y4 are independently selected from H, D, FG, or are absent;with the proviso that any of R1, R2, R3, or R4 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, R1-R4 are independently selected from the group consisting of H, D, FG, (C1-C6)alkyl, substituted (C1-C6)alkyl, (C1-C6)alkenyl, substituted (C1-C6)alkenyl, (C1-C6)alkynyl, substituted (C1-C6)alkynyl, hetero-(C1-C6)alkyl, substituted hetero-(C1-C6)alkyl, hetero-(C1-C6)alkenyl, substituted hetero-(C1-C6)alkenyl, hetero-(C1-C6)alkynyl, substituted hetero-(C1-C6)alkynyl, (C1-C6)cycloalkyl, substituted (C1-C6)cycloalkyl, aryl, substituted aryl, heterocycle, and substituted heterocycle;R5 and R6 are independently selected from the group consisting of H, D, FG, (C1-C6)alkyl, substituted (C1-C6)alkyl, (C1-C6)alkenyl, substituted (C1-C6)alkenyl, (C1-C6)alkynyl, substituted (C1-C6)alkynyl, hetero-(C1-C6)alkyl, substituted hetero-(C1-C6)alkyl, hetero-(C1-C6)alkenyl, substituted hetero-(C1-C6)alkenyl, hetero-(C1-C6)alkynyl, substituted hetero-(C1-C6)alkynyl, (C1-C6)cycloalkyl, substituted (C1-C6)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;R7 and R8 are independently selected from the group consisting of H, D, FG, (C1-C6)alkyl, substituted (C1-C6)alkyl, (C1-C6)alkenyl, substituted (C1-C6)alkenyl, (C1-C6)alkynyl, substituted (C1-C6)alkynyl, hetero-(C1-C6)alkyl, substituted hetero-(C1-C6)alkyl, hetero-(C1-C6)alkenyl, substituted hetero-(C1-C6)alkenyl, hetero-(C1-C6)alkynyl, substituted hetero-(C1-C6)alkynyl, (C1-C6)cycloalkyl, substituted (C1-C6)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;R9 and R10 are independently selected from the group consisting of H, D, FG, (C1-C6)alkyl, substituted (C1-C6)alkyl, (C1-C6)alkenyl, substituted (C1-C6)alkenyl, (C1-C6)alkynyl, substituted (C1-C6)alkynyl, hetero-(C1-C6)alkyl, substituted hetero-(C1-C6)alkyl, hetero-(C1-C6)alkenyl, substituted hetero-(C1-C6)alkenyl, hetero-(C1-C6)alkynyl, substituted hetero-(C1-C6)alkynyl, (C1-C6)cycloalkyl, substituted (C1-C6)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;R11 and R12 are independently selected from the group consisting of H, D, FG, (C1-C6)alkyl, substituted (C1-C6)alkyl, (C1-C6)alkenyl, substituted (C1-C6)alkenyl, (C1-C6)alkynyl, substituted (C1-C6)alkynyl, hetero-(C1-C6)alkyl, substituted hetero-(C1-C6)alkyl, hetero-(C1-C6)alkenyl, substituted hetero-(C1-C6)alkenyl, hetero-(C1-C6)alkynyl, substituted hetero-(C1-C6)alkynyl, (C1-C6)cycloalkyl, substituted (C1-C6)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;X1-X8 are independently selected from the group consisting of carbon and nitrogen;Y1-Y4 are independently selected from H, D, FG, or are absent; andwith the proviso that any of R1, R2, R3, or R4 are absent if bound to an X that is an N. 3. The conductive COF of claim 1, further comprising a core having a structure of Formula Ia: wherein, R60-R79 are independently selected from the group consisting of H, D, FG, (C1-C6)alkyl, substituted (C1-C6)alkyl, (C1-C6)alkenyl, substituted (C1-C6)alkenyl, (C1-C6)alkynyl, substituted (C1-C6)alkynyl, hetero-(C1-C6)alkyl, substituted hetero-(C1-C6)alkyl, hetero-(C1-C6)alkenyl, substituted hetero-(C1-C6)alkenyl, hetero-(C1-C6)alkynyl, substituted hetero-(C1-C6)alkynyl, (C1-C6)cycloalkyl, substituted (C1-C6)cycloalkyl, aryl, substituted aryl, heterocycle, and substituted heterocycle;R5 and R6 are independently selected from the group consisting of H, D, FG, (C1-C6)alkyl, substituted (C1-C6)alkyl, (C1-C6)alkenyl, substituted (C1-C6)alkenyl, (C1-C6)alkynyl, substituted (C1-C6)alkynyl, hetero-(C1-C6)alkyl, substituted hetero-(C1-C6)alkyl, hetero-(C1-C6)alkenyl, substituted hetero-(C1-C6)alkenyl, hetero-(C1-C6)alkynyl, substituted hetero-(C1-C6)alkynyl, (C1-C6)cycloalkyl, substituted (C1-C6)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;R7 and R8 are independently selected from the group consisting of H, D, FG, (C1-C6)alkyl, substituted (C1-C6)alkyl, (C1-C6)alkenyl, substituted (C1-C6)alkenyl, (C1-C6)alkynyl, substituted (C1-C6)alkynyl, hetero-(C1-C6)alkyl, substituted hetero-(C1-C6)alkyl, hetero-(C1-C6)alkenyl, substituted hetero-(C1-C6)alkenyl, hetero-(C1-C6)alkynyl, substituted hetero-(C1-C6)alkynyl, (C1-C6)cycloalkyl, substituted (C1-C6)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;R9 and R10 are independently selected from the group consisting of H, D, FG, (C1-C6)alkyl, substituted (C1-C6)alkyl, (C1-C6)alkenyl, substituted (C1-C6)alkenyl, (C1-C6)alkynyl, substituted (C1-C6)alkynyl, hetero-(C1-C6)alkyl, substituted hetero-(C1-C6)alkyl, hetero-(C1-C6)alkenyl, substituted hetero-(C1-C6)alkenyl, hetero-(C1-C6)alkynyl, substituted hetero-(C1-C6)alkynyl, (C1-C6)cycloalkyl, substituted (C1-C6)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;R11 and R12 are independently selected from the group consisting of H, D, FG, (C1-C6)alkyl, substituted (C1-C6)alkyl, (C1-C6)alkenyl, substituted (C1-C6)alkenyl, (C1-C6)alkynyl, substituted (C1-C6)alkynyl, hetero-(C1-C6)alkyl, substituted hetero-(C1-C6)alkyl, hetero-(C1-C6)alkenyl, substituted hetero-(C1-C6)alkenyl, hetero-(C1-C6)alkynyl, substituted hetero-(C1-C6)alkynyl, (C1-C6)cycloalkyl, substituted (C1-C6)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. 4. The conductive COF of claim 3, wherein one or more cores has a structure of Formula Ia: wherein, R5-R12, R60-R61, R63-R66, R68-R71, R73-R76, R78-R79 are H; andR62, R67, R72, and R77 are amine or aldehyde groups. 5. The conductive COF of claim 1, wherein the one or more linking moieties has a structure selected from the group consisting of Formula VII, VIII, and IX: wherein: n is a number from 1 to 8;A28-A44 are independently selected from C or N;R96-R125 are independently selected from the group consisting of H, D, FG, (C1-C20)alkyl, substituted (C1-C20)alkyl, (C1-C20)alkenyl, substituted (C1-C20)alkenyl, (C1-C20)alkynyl, substituted (C1-C20)alkynyl, hetero-(C1-C20)alkyl, substituted hetero-(C1-C20)alkyl, hetero-(C1-C20)alkenyl, substituted hetero-(C1-C20)alkenyl, hetero-(C1-C20)alkynyl, substituted hetero-(C1-C20)alkynyl, (C1-C20)cycloalkyl, substituted (C1-C20)cycloalkyl, aryl, substituted aryl, heterocycle, and substituted heterocycle;with the proviso that any of R98, R99, R101, R103, R105-R108, R110, R113, R115-R117, R120, and R122-R124 are absent if bound to an X that is an N. 6. The conductive COF of claim 1, wherein the one or more linking moieties has a structure of: 7. The conductive COF of claim 1, wherein the one or more linking moieties has a structure selected from the group consisting of: 8. The conductive organic-framework of claim 1, wherein the framework is post-synthesis functionalized to comprise a metal or conductive moiety. 9. The conductive organic-framework of claim 1, wherein the COF has hole conducting mobilities of at least 3.0 cm2V−1s−1. 10. The conductive organic-framework of claim 9, wherein the COF has hole conducting mobilities of at least 8.0 cm2V−1s−1. 11. The conductive organic-framework of claim 1, wherein the COF can hold a charge for at least 75 μs. 12. A flexible display comprising the conductive organic-framework of claim 1. 13. A semiconductor comprising the conductive organic-framework of claim 1. 14. A gas storage device comprising the conductive organic-framework of claim 1. 15. A chemical sensor comprising the conductive organic-framework of claim 1. 16. The COF of claim 1, wherein the COF has the structure and properties of COF-366.
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