Design and synthesis of porphyrin materials for highly efficient organic photovoltaics

A porphyrin small molecule having a molecular formula represented by Type 1, Type 2, Type 3, or Type 4:

• wherein,
• m is an integer selected from 2, 3, 4, or 5;
• M is selected from the group consisting of Fe2+, Fe3+, Co2+, Co3+, Ni2+, Zn2+, Cu2+, Ru2+, Pd2+, and Pt2+;
• Ar1 for each occurrence is independently selected from the group consisting of:
• Ar2 for each occurrence is independently selected from the group consisting of:
• A1 for each instance is independently selected from the group consisting of hydrogen, alkyl, cycloalkyl, cyclohexyl, cycloheptyl, cyclooctytl, haloalkyl, perhaloalkyl, ether, —R3, —CH(R3)(R4), —CH2CH(R3)(R4), —CH2CH2CH(R3)(R4), —CH2(OCH2CH2)nOCH3, —CH2(OCH2CH2)2OCH3, —CH2(CH2)nCF3, —CH2(CH2)5CF3, and —CF2(CF2)5CF3;
• A2 for each instance is independently selected from the group consisting from the group consisting of:
• A3 for each instance is independently selected fro the group consisting of:
• each instance of R1, R2, R5, and R6, is independently selected from the group consisting of hydrogen, halogen, cyano, alkyl, haloalkyl, alkoxy, haloalkoxy, aryl, haloaryl, aryloxy, halogenated aryloxy, cycloalkyl, heterocyclic alkyl, halogenated heterocyclic alkyl, heterocyclic alkoxy, halogenated heterocyclic alkoxy, heteroaryl, halogenated heteroaryl, heteroaryloxy, halogenated heterocyclic aryloxy, amino, halogenated amino, nitro
• R3 and R4 are independently selected from the group consisting of C1-C20 alkyl, C2-C8 alkyl, C4-C12 alkyl, C5-C8 alkyl, cycloalkyl, alkoxyl, aryloxyl, thioalkoxyl, and thioaryloxyl.