Fusing porphyrins with polycyclic aromatic hydrocarbons and heterocycles for optoelectronic applications

摘要

A compound that can be used as a donor material in organic photovoltaic devices comprising a non-activated porphyrin fused with one or more non-activated polycyclic aromatic rings or one or more non-activated heterocyclic rings can be obtained by a thermal fusion process. The compounds can include structures of Formula I:;
By heating the reaction mixture of non-activated porphyrins with non-activated polycyclic aromatic rings or heterocyclic rings to a fusion temperature and holding for a predetermined time, fusion of one or more polycyclic rings or heterocyclic rings to the non-activated porphyrin core in meso,β fashion is achieved resulting in hybrid structures containing a distorted porphyrin ring with annulated aromatic rings. The porphyrin core can be olygoporphyrins.

主权项

1. A compound comprising a non-activated porphyrin fused with one or more non-activated polycyclic aromatic rings, said compound having a formula selected from the group consisting of: M is any element selected from the group consisting of Mg, Ca, Sr, Ba, Sc, Y, La, Ce, Ti, Nb, Ta, Cr, Mo, W, Mn, Tc, Re, Fe, Ru, Os, Co, Rh, Ir, Ni, Pd, Pt, Cu, Ag, Au, Zn, Cd, Hg, Al, Ga, In, Ti, Si, Ge, Sn, Pb, P, As, Sb, Bi, Pr, Nd, Sm, Eu, Gd, Tb, Dy, Ho, Er, Tm, Yb, Lu, Th, and U; wherein R1, R3-R5, R7-R8 and R51-R82 are independently selected from the group consisting of hydrogen, alkyl, fluoroalkyl, hydroxyl, halo, mercapto group, amino, cyano, alkenyl, alkynyl, and aryl, wherein R2 and R6 are independently selected from the group consisting of hydrogen, alkyl, fluoroalkyl, hydroxyl, alkoxy, halo, mercapto group, amino, cyano, alkenyl, alkynyl, 3,5-di-tert-butylphenyl, and aryl, and wherein adjacent substituents R51-R82 optionally form fused rings, wherein the fused rings are aromatic, unsaturated, or combinations of both aromatic and unsaturated rings, including four, five, six, seven, eight, or nine-membered rings, wherein the fused rings can include one or more heteroatoms independently selected from the group consisting of O, S, Se, Te, N, P, As, Si, Ge, and B.