Recyclable and reconfigurable high-performance polymer networks and uses thereof

A composition comprising a polymer, or polymer network, having at least one unit of the formula (I), (II), (III), (IV), (V), (VI), (VII), (VIII), (IX), (X), (XI), (XII), (XIII), (XIV), (XV), (XVI), (XVII), (XVIII), (XIX), and/or (XX), or a mixture thereof;

• wherein said polymer, or polymer network, is obtained by connecting one compound Y comprising at least two functional groups selected from the group (A), (B), (C), (D), (E), (F), (G), (H), (I), (J), (K), (L), (M), (N), (O), (P), (Q), (R), (S), (T), (U), (V), and/or (W), or a mixture thereof;
• with at least one compound Z comprising at least two amine functional groups of the type —NH2, —NHR4, —NH3+ and/or —NHR4R5+ groups, or at least two functional groups that generates —NH2, —NHR4, —NH3+ and/or —NHR4R5+ in situ, or a mixture thereof;
• wherein said amine is optionally (C1-20)alkyl, (C2-20)alkenyl;
• (C2-20)alkynyl;
• (C6-12)aryl, (C3-8)cycloalkyl;
• (C6-12)aryl (C1-20)alkyl;
• (C3-8)cycloalkyl(C1-20)alkyl;
• hetero(C1-20)alkyl;
• heterocyclyl;
• heterocyclyl(C1-20)alkyl;
• heteroaryl;
• or heteroaryl(C1-20)alkyl;
• wherein said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C3-8)cycloalkyl(C1-20)alkyl;
• (C6-12)aryl(C1-20)alkyl, heterocyclyl(C1-20)alkyl;
• and heteroaryl(C1-20)alkyl, optionally comprises one or more heteroatoms in the alkyl, alkenyl, alkynyl, moiety, said heteroatoms being each independently a C, Si, chalcogenide (such as O, S, or Se), or a pnictide (such as N, or P);
• wherein at least one carbon atom or heteroatom of said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl (C1-20)alkyl, hetero(C1-20)alkyl;
• heterocyclyl;
• heteroaryl;
• (C3-8)cycloalkyl(C1-20)alkyl;
• heterocyclyl(C1-20)alkyl;
• and heteroaryl(C1-20)alkyl;
• can optionally be oxidized to form at least one C═O, C═S, N═O, N═S, S═O or S(O)2;
• wherein said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-s) cycloalkyl, (C6-12)aryl (C1-20)alkyl, hetero(C1-20)alkyl;
• heterocyclyl;
• heteroaryl;
• (C3-8)cycloalkyl (C1-20)alkyl;
• heterocyclyl(C1-20)alkyl;
• and heteroaryl(C1-20)alkyl;
• can be unsubstituted or substituted with one or more Z1;
• each Z1 is independently selected from the group consisting of halogen;
• (C1-20)alkyl;
• (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
• heterocyclyl;
• heteroaryl;
• (C3-8)cycloalkyl(C1-20)alkyl;
• heterocyclyl(C1-20)alkyl;
• heteroaryl(C1-20)alkyl;
• halo(C1-20)alkyl;
• halo(C1-20)alkyloxy;
• —OR5, —SR5;
• —S(O)R4;
• —S(O)2R4;
• —SO2NR6R7;
• —NO2;
• —NR5C(O)R4, —NR5S(O)2R4;
• —NR5C(O)NR6R7, NR6R7;
• cyano;
• —CO2R5;
• —C(O)NR6R7;
• and —C(O)R4, and wherein the ratio R is less than, or equal to 1 (R≤1), where R=(sum (functionality of compound Y (FY)×number of moles of compound Y (NY))/(sum (functionality of compound Z (FZ)×number of moles of all molecules of compound Z (NZ)).
• R
• =
• ∑
• F
• Y
• ⁢
• N
• Y
• ∑
• F
• Z
• ⁢
• N
• Z
• ≤
• 1
• ;
• wherein R1 is selected from the group consisting of (C1-20)alkyl, (C2-20)alkenyl;
• (C2-20)alkynyl;
• (C6-12)aryl, (C3-8)cycloalkyl;
• (C6-12)aryl (C1-20)alkyl;
• (C3-8)cycloalkyl(C-20)alkyl, hetero(C1-20)alkyl;
• heterocyclyl;
• heterocyclyl(C1-20)alkyl;
• heteroaryl;
• and heteroaryl(C1-20)alkyl;
• wherein said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C3-8)cycloalkyl(C1-20)alkyl;
• (C6-12)aryl(C1-20)alkyl, heterocyclyl(C1-20)alkyl;
• and heteroaryl(C1-20)alkyl, optionally comprises one or more heteroatoms in the alkyl, alkenyl, alkynyl moiety, each heteroatom is independently a C, Si, chalcogenide (such as O, S, or Se), or a pnictide (such as N, or P);
• wherein at least one carbon atom or heteroatom of said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl (C1-20)alkyl, hetero(C1-20)alkyl;
• heterocyclyl;
• heteroaryl;
• (C3-8)cycloalkyl(C1-20)alkyl;
• heterocyclyl(C1-20)alkyl;
• and/or heteroaryl(C1-20)alkyl;
• can be oxidized to form at least one C═O, C═S, N═O, N═S, S═O or S(O)2;
• wherein said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl, heterocyclyl;
• heteroaryl;
• (C3-8)cycloalkyl (C1-20)alkyl;
• heterocyclyl(C1-20)alkyl;
• and/or heteroaryl(C1-20)alkyl;
• is unsubstituted or substituted with one or more Z1;
• each Z1 is independently selected from the group consisting of halogen;
• (C1-20)alkyl;
• (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
• heterocyclyl;
• heteroaryl;
• (C3-8)cycloalkyl(C1-20)alkyl;
• heterocyclyl(C1-20)alkyl;
• heteroaryl(C1-20)alkyl;
• halo(C1-20)alkyl;
• halo(C1-20)alkyloxy;
• —OR5;
• —SR5;
• —S(O)R4;
• —S(O)2R4;
• —SO2NR6R7;
• nitro;
• —NR5C(O)R4;
• —NR5S(O)2R4;
• —NR5C(O)NR6R7;
• NR6R7;
• cyano;
• —CO2R5;
• —C(O)NR6R7;
• and —C(O)R4;
• and
• wherein R2 is selected from the group consisting of (C1-20)alkyl, (C2-20)alkenyl;
• (C2-20)alkynyl;
• (C6-12)aryl, (C3-8)cycloalkyl;
• (C6-12)aryl (C1-20)alkyl;
• (C3-8)cycloalkyl (C1-20)alkyl;
• hetero(C1-20)alkyl;
• heterocyclyl;
• heterocyclyl(C1-20)alkyl;
• heteroaryl;
• and heteroaryl(C1-20)alkyl;
• wherein said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C3-8)cycloalkyl(C1-20)alkyl;
• (C6-12)aryl(C1-20)alkyl, heterocyclyl(C1-20)alkyl;
• and heteroaryl(C1-20)alkyl, optionally comprises one or more heteroatoms in the alkyl, alkenyl, alkynyl moiety, each heteroatom is independently a C, Si, chalcogenide (such as O, S, or Se), or a pnictide (such as N, or P);
• wherein at least one carbon atom or heteroatom of said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
• heterocyclyl;
• heteroaryl;
• (C3-8)cycloalkyl(C1-20)alkyl;
• heterocyclyl(C1-20)alkyl;
• and/or heteroaryl(C1-20)alkyl;
• can be oxidized to form at least one C═O, C═S, N═O, N═S, S═O or S(O)2;
• wherein said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl (C1-20)alkyl, hetero(C1-20)alkyl;
• heterocyclyl;
• heteroaryl;
• (C3-8)cycloalkyl (C1-20)alkyl;
• heterocyclyl(C1-20)alkyl;
• and/or heteroaryl(C1-20)alkyl;
• is unsubstituted or substituted with one or more Z1;
• each Z1 is independently selected from the group consisting of halogen;
• (C1-20)alkyl;
• (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl (C1-20)alkyl, hetero(C1-20)alkyl;
• heterocyclyl;
• heteroaryl;
• (C3-8)cycloalkyl(C1-20)alkyl;
• heterocyclyl(C1-20)alkyl;
• heteroaryl(C1-20)alkyl;
• halo(C1-20)alkyl;
• halo(C1-20)alkyloxy;
• —OR5;
• —SR5;
• —S(O)R4;
• —S(O)2R4;
• —SO2NR6R7;
• nitro;
• —NR5C(O)2R4;
• —NR5S(O)2R4;
• —NR5C(O)NR6R7;
• NR6R7;
• cyano;
• —CO2R5;
• —C(O)NR6R7;
• and —C(O)2R4;
• and
• wherein R2 and R3 are optionally directly bonded together to form a, 5 membered cycloalkyl, heterocyclyl, or heteroaryl;
• wherein R2 and R3 are optionally bonded together with a linker X1 to form a 6, 7, or 8 membered cycloalkyl, heterocyclyl, or heteroaryl;
• wherein X1 within said cycloalkyl, heterocyclyl, or heteroaryl is independently selected from the group consisting of C, Si, chalcogenide (preferably O, S, or Se), or a pnictide (preferably N, or P);
• wherein each said heterocyclyl;
• or heteroaryl is independently optionally substituted with one or more Z2 wherein each Z2 is independently selected from the following group consisting of halogen;
• (C1-20)alkyl;
• (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
• heterocyclyl;
• heteroaryl;
• (C3-8)cycloalkyl(C1-20)alkyl;
• heterocyclyl(C1-20)alkyl;
• heteroaryl(C1-20)alkyl;
• halo(C1-20)alkyl;
• halo(C1-20)alkyloxy;
• —OR5;
• —SR3;
• —S(O)R4, —S(O)2R4;
• —SO2NR6R7;
• nitro;
• —NR5C(O)R4;
• —NRSS(O)R4;
• —NR5C(O)NR6R7;
• NR6R7;
• cyano;
• —CO2R5;
• —C(O)NR6R7;
• and —C(O)R4;
• wherein R2 and R1 are optionally directly bonded together to form a, 5 membered cycloalkyl, heterocyclyl, or heteroaryl;
• wherein R2 and R1 are optionally bonded together with a linker X1 to form a 6, 7, or 8 membered cycloalkyl, heterocyclyl, or heteroaryl;
• wherein X1 within said cycloalkyl, heterocyclyl, or heteroaryl is independently selected from the group consisting of C, Si, chalcogenide (such as O, S, or Se), or a pnictide (such as N, or P);
• wherein X1 and R2 are optionally directly bonded together to form a, 5, 6, 7, or 8 membered heterocyclyl, or heteroaryl;
• wherein X1 and R3 are optionally directly bonded together to form a, 5, 6, 7, or 8 membered cycloalkyl, heterocyclyl, or heteroaryl;
• wherein each said heterocyclyl;
• or heteroaryl is optionally substituted with one or more Z2 where each Z2 is independently selected from the following group consisting of halogen;
• (C1-20)alkyl;
• (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl (C1-20)alkyl, hetero(C1-20)alkyl;
• heterocyclyl;
• heteroaryl;
• (C3-8)cycloalkyl (C1-20)alkyl;
• heterocyclyl(C1-20)alkyl;
• heteroaryl(C1-20)alkyl;
• halo(C1-20)alkyl;
• halo(C1-20)alkyloxy;
• —OR5;
• —SR5;
• —S(O)R4;
• —S(O)2R4;
• —SO2NR5R6;
• nitro;
• —NR5C(O)R4;
• —NR5S(O)2R4;
• —NR5C(O)NR6R7;
• NR6R7;
• cyano;
• —CO2R5;
• —C(O)NR6R7;
• and —C(O)R4,
• wherein R3 is selected from the group consisting of (C1-20)alkyl, (C2-20)alkenyl;
• (C2-20)alkynyl;
• (C6-12)aryl, (C3-8)cycloalkyl;
• (C6-12)aryl (C1-20)alkyl;
• (C3-8)cycloalkyl (C1-20)alkyl;
• hetero(C1-20)alkyl;
• heterocyclyl;
• heterocyclyl(C1-20)alkyl;
• heteroaryl;
• and heteroaryl(C1-20)alkyl;
• wherein said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C3-8)cycloalkyl(C1-20)alkyl;
• (C6-12)aryl (C1-20)alkyl, heterocyclyl(C1-20)alkyl;
• and heteroaryl(C1-20)alkyl, optionally comprises one or more heteroatoms in the alkyl, alkenyl, alkynyl moiety, each heteroatom is independently a C, Si, chalcogenide (such as O, S, or Se), or a pnictide (such as N, or P);
• wherein at least one carbon atom or heteroatom of said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl (C1-20)alkyl, hetero(C1-20)alkyl;
• heterocyclyl;
• heteroaryl;
• (C3-8)cycloalkyl(C1-20)alkyl;
• heterocyclyl(C1-20)alkyl;
• and heteroaryl(C1-20)alkyl;
• is optionally oxidized to form at least one C═O, C═S, N═O, N═S, S═O or S(O)2;
• wherein said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl (C1-20)alkyl, hetero(C1-20)alkyl;
• heterocyclyl;
• heteroaryl;
• (C3-8)cycloalkyl (C1-20)alkyl;
• heterocyclyl(C1-20)alkyl;
• and heteroaryl(C1-20)alkyl;
• is unsubstituted or substituted with one or more Z1;
• wherein each Z1 is independently selected from the group consisting of halogen;
• (C1-20)alkyl;
• (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
• heterocyclyl;
• heteroaryl;
• (C3-8)cycloalkyl(C1-20)alkyl;
• heterocyclyl(C1-20)alkyl;
• heteroaryl(C1-20)alkyl;
• halo(C1-20)alkyl;
• halo(C1-20)alkyloxy;
• —OR5;
• —SR5;
• —S(O)R4, —S(O)2R4;
• —SO2NR6R7;
• nitro;
• —NR5C(O)R4;
• —NR5S(O)2R4;
• —NR5C(O)NR67;
• cyano;
• —CO2R5;
• —C(O)NR67;
• and —C(O)R4;
• and wherein R3 and R1 are optionally directly bonded together to form a, 5 membered cycloalkyl, heterocyclyl, or heteroaryl;
• wherein R3 and R1 are optionally bonded together with a linker X1 to form a 6, 7, or 8 membered cycloalkyl, heterocyclyl, or heteroaryl;
• wherein X1 within said cycloalkyl, heterocyclyl, or heteroaryl is independently selected from the group consisting of C, Si, chalcogenide (such as O, S, or Se), or a pnictide (such as N, or P);
• wherein each said heterocyclyl;
• or heteroaryl is optionally substituted with one or more Z2 where each Z2 is independently selected from the following group consisting of halogen;
• (C1-20)alkyl;
• (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl (C1-20)alkyl, hetero(C1-20)alkyl;
• heterocyclyl;
• heteroaryl;
• (C3-8)cycloalkyl (C1-20)alkyl;
• heterocyclyl(C1-20)alkyl;
• heteroaryl(C1-20)alkyl;
• halo(C1-20)alkyl;
• halo(C1-20)alkyloxy;
• —OR5;
• —SR5;
• —S(O)R4;
• —S(O)2R4;
• —SO2NR5R6;
• nitro;
• —NR5C(O)R4;
• —NR5S(O)2R4;
• —NR67C(O)NR6R7;
• NR6R7;
• cyano;
• —CO2R5;
• —C(O)NR6R7;
• and —C(O)R4
• wherein R3 is linked to R1 with a linker X1 to form a 4, 5, 6, or 7 membered cycloalkyl, heterocyclyl, or heteroaryl;
• wherein X1 within said cycloalkyl, heterocyclyl, or heteroaryl is independently selected from the group consisting of C, Si, chalcogenide (preferably O, S, or Se), or a pnictide (preferably N, or P);
• wherein each said heterocyclyl;
• or heteroaryl is optionally substituted with one or more Z2 where each Z2 is independently selected from the following group consisting of halogen;
• (C1-20)alkyl;
• (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
• heterocyclyl;
• heteroaryl;
• (C3-8)cycloalkyl (C1-20)alkyl;
• heterocyclyl(C1-20)alkyl;
• heteroaryl(C1-20)alkyl;
• halo(C1-20)alkyl;
• halo(C1-20)alkyloxy;
• —OR5, —SR5;
• —S(O)R4, —S(O)2R4, —SO2NR5R6;
• nitro;
• —NR5C(O)R4, —NR5S(O)2R4;
• —NR5C(O)NR6R7;
• NR6R7;
• cyano;
• —CO2R5;
• —C(O)NR6R7, and —C(O)R4;
• each R4 is independently selected from the group consisting of hydrogen, C(1-20)alkyl, C(2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl (C1-20)alkyl, hetero(C1-20)alkyl;
• heterocyclyl;
• heteroaryl;
• heterocyclyl (C1-20)akyl;
• and heteroaryl(C1-20)alkyl;
• wherein said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl (C1-20)alkyl, heterocyclyl(C1-20)alkyl;
• heteroaryl(C1-20)alkyl, optionally comprise one or more heteroatoms in the alkyl, alkenyl or alkynyl moiety, said heteroatoms being each independently selected from O, S and N;
• and wherein at least one carbon atom or heteroatom of said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl (C1-20)alkyl, hetero(C1-20)alkyl;
• heterocyclyl;
• heteroaryl;
• heterocyclyl(C1-20)alkyl;
• and heteroaryl(C1-20)alkyl;
• is optionally oxidized to form at least one C═O, C═S, N═O, N═S, S═O or S(O)2;
• each R5 is independently selected from the group consisting of hydrogen, (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
• heterocyclyl;
• heteroaryl;
• heterocyclyl(C1-20)akyl;
• and heteroaryl(C1-20)alkyl;
• wherein said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl(C1-20)alkyl, heterocyclyl(C1-20)alkyl;
• heteroaryl(C1-20)alkyl, optionally comprise one or more heteroatoms in the alkyl, alkenyl or alkynyl moiety, said heteroatoms being each independently selected from O, S and N;
• and wherein at least one carbon atom or heteroatom of said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
• heterocyclyl;
• heteroaryl;
• heterocyclyl(C1-20)alkyl;
• and heteroaryl(C1-20)alkyl;
• is optionally oxidized to form at least one C═O, C═S, N═O, N═S, S═O or S(O)2;
• each R6 and R7 is independently selected from the group consisting of hydrogen;
• (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
• heterocyclyl;
• heteroaryl;
• heterocyclyl(C1-20)alkyl;
• and heteroaryl(C1-20)alkyl;
• wherein said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C3-8)cycloalkyl(C1-20)alkyl;
• (C6-12)aryl (C1-20)alkyl, heterocyclyl(C1-20)alkyl;
• and heteroaryl(C1-20)alkyl, optionally comprises one or more heteroatoms in the alkyl, alkenyl, alkynyl moiety, each heteroatom is independently a C, Si, chalcogenide (such as O, S, or Se), or a pnictide (such as N, or P);
• and wherein at least one carbon atom or heteroatom of said (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl;
• heterocyclyl;
• heteroaryl;
• heterocyclyl(C1-20)alkyl;
• and heteroaryl(C1-20)alkyl, is optionally oxidized to form at least one C═O, C═S, N═O, N═S, S═O or S(O)2;
• or wherein R6 and R7 together with the atom to which they are attached form a 5-, 6-, or 7-membered heterocyclyl.