Electron-deficient fluorous porphyrins and methods of making and their use in organic solar cells

An electron deficient fluorous porphyrin having the structure (I):

• in which each R1, R2, R3, R4 is independently an aryl group bearing substituents having 3 to 60 carbon atoms and other atoms including one or more of F, Cl, Br, N, O, S, P and H;
• each R5, R6, R7, R8, R5′, R6′, R7′, R8′, R5″, R6″, R7″, R8″, R5′″, R6′″, R7′″, R8′″ are each independently a perfluoroalkyl group with a formula of CmF(2m+1) or a perfluoropolyether group with a formula of CkF(2k+1)Ox wherein m is integer from 1 to 30, k is an integer from 1 to 1000 and x is an integer less than k;
• or R5, R6, R7, R8, R5′, R6′, R7′, R8′, R5″, R6″, R7″, R8″, R5′″, R6′″, R7′″, R8′″ are each independently combination of perfluoroalkyl group with a formula of CmF(2m+1) wherein m is integer from 1 to 30, a perfluoropolyether group with a formula of CkF(2k+1)Ox wherein k isinteger from 1 to 1000, wherein x is an integer from 1 to k−1, or groups having 3 to 60 carbons and other atoms including one or more of F, Cl, Br, N, O, S, P and H, wherein the group of substituents R5, R6, R7, R8, R5′, R6′, R7′, R8′, R5″, R6″, R7″, R8″, R5′″, R6′″, R7′″, R8′″ includes at least two of the perfluoroalkyl group, the perfluoropolyether group, and the group having 3 to 60 carbons and other atoms;
• n is integer from 1 to 3;
• and
• M is selected from the group consisting of 2H, Li, Na, K, Mg, Ca, Al, P, S, Se, As, Ge, Ga, In, Sn, Sb, TI, Pb, Bi, Sr, Ba, Sc, Y, Ti, V, Cr, Mn, Zr, Nb, Mo, Ru, Rh, Pd, Ag, Cd, Fe, Co, Ni, Cu, Au, Hf, Ta, W, Re, Os, Ir, Pt, Zn, Hg and Lanthanides with formal oxidation states from +1 to +6.