Dyes with phosphinic acid, phosphinate, phosphonate and phosphonamidate substituents as auxochromic groups and methods for preparing the same

A compound which is a fluorescent dye and has the structural formula:

• wherein:
• each of X1, X2, X3 and X4 is a member independently selected from the group consisting of H, F, Cl, Br, I, CN, NO2, OR1, SR1, NR1R2, COR1, COOR1, CONR1R2, PO3R1R2, SO2R1, SO3R1 and R3, where:
• R1 and R2 are independently selected from H, alkyl, aryl or heteroaryl, and R1 and R2 can optionally form together a substituted or unsubstituted 4-7 membered ring;
• R3 is alkyl, alkenyl, alkynyl, aryl or cycloalkyl, optionally substituted with one or more heteroatoms independently selected from N, O, S, F, Cl, Br, I, N3, amine, OH, OR1, OCOR1, aryl, COOR1, CONR1R2, PO3H2 and SO3H, where R1 and R2 are defined as above;
• Y is selected from OR1, NR1R2, or NR1R3, where R1, R2 and R3 are defined as above;
• Q is selected from O, S, SO2, NR3, C(R3)2, Si(R3)2, Ge(R3)2, P(═O)R3, or P(═O)OR3, where R3 is defined as above, and wherein Q and X1, taken together with the atoms to which they are bonded, can optionally form a substituted or unsubstituted 5-7 membered ring;
• L and M are independently selected from OR1, SR1, NR1R2 or R3, where R1, R2 and R3 are defined as above, and wherein L and M, taken together with the atoms to which they are bonded, can optionally form a substituted or unsubstituted 5-7 membered ring;
• and
• Z is selected from O, S, NR1, CR1R3 or aryl, where R1 and R3 are defined as above, and wherein Z and X4, taken with the atoms to which they are bonded, can optionally form a substituted or unsubstituted 5-7 membered ring.