Substituted azadibenzocyclooctyne compounds and their use in metal-free click reactions

A compound of the Formula (5):

• wherein:
• R1, R2, R3, R4, R5, R6, R7 and R8 are independently selected from the group consisting of hydrogen, halogen, C1-C12 haloalkyl, —CN, —N3, —NO2, —NCX, —XCN, —N(R9)2, —N+(R9)3, —C(X)N(R9)2, —C(X)R9, —C(X)XR9, —S(O)R9, —S(O)2R9, —S(O)OR9, —S(O)2OR9, —S(O)N(R9)2, —S(O)2N(R9)2, —OS(O)R9, —OS(O)2R9, —OS(O)OR9, —OS(O)2OR9, —P(O)(R9)(OR9), —P(O)(OR9)2, —OP(O)(OR9)2, —XC(X)R9, —XC(X)XR9, —XC(X)N(R9)2, —N(R9)C(X)R9, —N(R9)C(X)XR9 and —N(R9)C(X)N(R9)2, wherein X is oxygen or sulfur and wherein R9 is independently selected from the group consisting of hydrogen, halogen, C1-C24 alkyl groups, C2-C24 (hetero)aryl groups, C3-C24 alkyl(hetero)aryl groups and C3-C24 (hetero)arylalkyl groups;
• with the proviso that at least one of R1, R2, R3, R4, R5, R6, R7 and R8 is selected from the group consisting of halogen, C1-C12 haloalkyl, —CN, —N3, —NO2, —NCX, —XCN, —N(R9)2, —N+(R9)3, —C(X)N(R9)2, —C(X)R9, —C(X)XR9, —S(O)R9, —S(O)2R9, —S(O)OR9, —S(O)2OR9, —S(O)N(R9)2, —S(O)2N(R9)2, —OS(O)R9, —OS(O)2R9, —OS(O)OR9, —OS(O)2OR9, —P(O)(R9)(OR9), —P(O)(OR9)2, —OP(O)(OR9)2, —XC(X)R9, —XC(X)XR9, —XC(X)N(R9)2, —N(R9)C(X)R9, —N(R9)C(X)XR9 and —N(R9)C(X)N(R9)2, wherein X and R9 are as defined above;
• p is 0 or 1;
• L is a linking group selected from the group consisting of linear or branched C1-C200 alkylene groups, C2-C200 alkenylene groups, C2-C200 alkynylene groups, C3-C200 cycloalkylene groups, C5-C200 cycloalkenylene groups, C8-C200 cycloalkynylene groups, C2-C200 (hetero)arylene groups, C3-C200 alkyl(hetero)arylene groups, C3-C200 (hetero)arylalkylene groups, C4-C200 (hetero)arylalkenylene groups, C5-C200 (hetero)arylalkynylene groups, the alkylene groups, alkenylene groups, alkynylene groups, cycloalkylene groups, cycloalkenylene groups, cycloalkynylene groups, (hetero)arylene groups, alkyl(hetero)arylene groups, (hetero)arylalkylene groups, (hetero)arylalkenylene groups, (hetero)arylalkynylene groups optionally being substituted and/or optionally interrupted by one or more heteroatoms;
• and
• Q is a functional group selected from the group consisting of hydrogen, halogen, R11, —CH═C(R11)2, —C≡CR11, —[C(R11)2C(R11)2O]q—R11 wherein q is in the range of 1 to 200, —CN, —N3, —NCX, —XCN, —XR11, —N(R11)2, —+N(R11)3, —C(X)N(R11)2, —C(R11)2XR, —C(X)R11, —C(X)XR11, —S(O)R11, —S(O)2R11, —S(O)OR11, —S(O)2OR11, —S(O)N(R11)2, —S(O)2N(R11)2, —OS(O)R11, —OS(O)2R11, —OS(O)OR11, —OS(O)2OR11, —P(O)(R11)(OR11), —P(O)(OR11)2, —OP(O)(OR11)2, —Si(R11)3, —XC(X)R11, —XC(X)XR11, —XC(X)N(R11)2, —N(R11)C(X)R11, —N(R11)C(X)XR11 and —N(R11)C(X)N(R11)2, wherein X is oxygen or sulphur and wherein R11 is independently selected from the group consisting of hydrogen, halogen, C1-C24 alkyl groups, C2-C24 (hetero)aryl groups, C3-C24 alkyl(hetero)aryl groups and C3-C24 (hetero)arylalkyl groups.