Probes for imaging b-amyloid and inhibition of β-amyloid aggregation

An aggregation-induced emission luminogen (AIEgen) having a Formula 1:

• or a pharmaceutically acceptable salt thereof, wherein:
• m is a whole number selected from 1-4;
• n for each instance is a whole number selected from 1-6;
• p is a whole number selected from 1-4;
• q is a whole number selected from 2-6;
• A is a bond or a moiety having the structure:
• Y is O, S, or —NR6—;
• X is —O(C═O)— or —(R4)C═C(R4)—;
• R1 for each instance is independently hydrogen, halide, cyano, nitro, —OR7, —SR7, —N(R7)2, —(C═O)R7, —(C═O)OR7, —(C═O)N(R7)2, —N(R7)(C═O)R7, —O(C═O)R7, —N(R7)(C═O)OR7, —O(C═O)N(R7)2, —SO2R7, —SO2N(R7)2, alkyl, cycloalkyl, alkenyl, alkynyl, aryl, aralkyl, heterocycloalkyl, heteroaryl, or —(CH2)nZ;
• R2 is a moiety having structure:
• R3 is hydrogen or cyano;
• R3 for each instance is independently hydrogen, alkyl, cycloalkyl, alkenyl, alkynyl, aryl, aralkyl, heterocycloalkyl, or heteroaryl;
• R5 is hydrogen, halide, cyano, nitro, —OR7, —SR7, —N(R7)2, —(C═O)R7, —(C═O)OR7, —(C═O)N(R7)2, —N(R7)(C═O)R7, —O(C═O)R7, —N(R7)(C═O)OR7, —O(C═O)N(R7)2, —SO2R7, —SO2N(R7)2, alkyl, cycloalkyl, alkenyl, alkynyl, aryl, aralkyl, heterocycloalkyl, heteroaryl, or —(CH2)nZ;
• R6 is hydrogen, alkyl, cycloalkyl, alkenyl, alkynyl, aryl, aralkyl, heterocycloalkyl, or heteroaryl;
• R7 for each occurrence is independently hydrogen, alkyl, cycloalkyl, alkenyl, alkynyl, aryl, aralkyl, heterocycloalkyl, heteroaryl, or —(CH2)2Z;
• or two instances of R7 taken together with the atom or atoms to which they are covalently bonded form a 3-7 membered cycloalkyl, or 3-7 membered heterocycloalkyl;
• R8 for each instance is independently hydrogen, halide, cyano, nitro, —OR7, —SR7, —N(R7)2, —(C═O)R7, —(C═O)OR7, —(C═O)N(R7)2, —N(R7)(C═O)R7, —O(C═O)R7, —N(R7)(C═O)OR7, —O(C═O)N(R7)2, —SO2R7, —SO2N(R7)2, alkyl, cycloalkyl, alkenyl, alkynyl, aryl, aralkyl, heterocycloalkyl, heteroaryl, or —(CH2)nZ;
• R9 is alkyl, cycloalkyl, alkenyl, alkynyl, aryl, aralkyl, heterocycloalkyl, heteroaryl, —(CH2)qOH, or —(CH2)qNH2;
• Q is an anion;
• and
• Z for each instance is independently halide, —C≡CH, —N3, —NCS, —NCO, —OR7, —SR7, —N(R7)2, —(C═O)R7, —(C═O)OR7, —(C═O)N(R7)2, —N(R7)(C═O)R7, —O(C═O)R7, —N(R7)(C═O)OR7, —O(C═O)N(R7)2, —SO2R7, —SO2N(R7)2, or N-maleimide.