Tethered Alkylidyne and Methods of Making the Same

A compound having a structure represented by formula (I) or formula (I-dimer):

• wherein the dashed lines are optional double bonds;
• M is a transition metal;
• L is a neutral or anionic ligand;
• each L′ is independently absent or a neutral or anionic ligand;
• Q is selected from S, O, N, NR5, N(R5)2, P(R6)2, C, CR7, C(R7)2, BR8, Si(R9)2, Se, and Te;
• X is selected from a bond, S, O, N, NR5, Se, Te, C1-C4haloalkyl, C1-C4alkyl, C2-C4alkenyl, C4-C10cycloalkyl, Ar1, C1-C4heteroalkyl comprising 1 to 5 heteroatoms selected from O, N, and S, and C1-C8heterocycloalkyl comprising 1 to 5 heteroatoms selected from O, N, and S;
• R3 is selected from a bond, —C(R1)2—, —C(R1)2C(R1)2—, —C(R1)2C(R1)2C(R1)2—, —C(R1)2C(R1)2C(R1)2C (R1)2—, and —C(R1)2C(R1)2C(R1)2C(R1)2C(R1)2—;
• each R1 is independently selected from H, C1-C20haloalkyl, C1-C20alkyl, C2-C20alkenyl, C4-C20cycloalkyl, Ar1, C1-C20heteroalkyl comprising 1 to 5 heteroatoms selected from O, N, and S, and C1-C20heterocycloalkyl comprising 1 to 5 heteroatoms selected from O, N, and S, or two geminal R1 together with the carbon atom to which they are attached, form a five- to eight-member cycloalkyl or heterocycloalkyl comprising 1 to 5 heteroatoms selected from O, N, and S, or two vicinal R1 together with the carbon atoms to which they are attached, form a six-member aryl or heteroaryl comprising 1 to 4 heteroatoms selected from O, N, and S, or a five- to eight-member cycloalkyl or heterocycloalkyl comprising 1 to 5 heteroatoms selected from O, N, and S;
• each R2 is independently selected from H, C1-C20haloalkyl, C1-C20alkyl, C2-C20alkenyl, C4-C20cycloalkyl, Ar1, C1-C20heteroalkyl comprising 1 to 5 heteroatoms selected from O, N, and S, and C1-C20heterocycloalkyl comprising 1 to 5 heteroatoms selected from O, N, and S, or both R2 together with the carbon atoms to which they are attached, form a five- to eight-member cycloalkyl or heterocycloalkyl comprising 1 to 5 heteroatoms selected from O, N, and S;
• each R6 and R9 are independently selected from C1-C22 alkyl, C4-C8 cycloalkyl, Ar1, C1-C20heteroalkyl comprising 1 to 5 heteroatoms selected from O, N, and S, and C1-C20heterocycloalkyl comprising 1 to 5 heteroatoms selected from O, N, and S, or two vicinal R5, two vicinal R6, two vicinal R8, or two vicinal R9, together with the atoms to which they are attached, form a five- to eight-member cycloalkyl, aryl, heteroaryl, or heterocycloalkyl comprising 1 to 5 heteroatoms selected from O, N, and S;
• each R5, R7, and R8 are independently selected from H, C1-C22 alkyl, C4-C8 cycloalkyl, Ar1, C1-C20heteroalkyl comprising 1 to 5 heteroatoms selected from O, N, and S, and C1-C20heterocycloalkyl comprising 1 to 5 heteroatoms selected from O, N, and S, or two vicinal R7 together with the atoms to which they are attached, form a five- to eight-member cycloalkyl, aryl, heteroaryl, or heterocycloalkyl comprising 1 to 5 heteroatoms selected from O, N, and S;
• and,
• each Ar1 is independently selected from C6-C22 aryl and a 5-12 membered heteroaryl comprising from 1 to 3 ring heteroatoms selected from O, N, and S.