Regioisomerically pure oxochlorins and methods of synthesis

A trans substituted oxochlorin compound of Formula X:

• wherein:
• M is a metal selected from the group consisting of Zn, Mg, Pt, Pd, Sn and Al;
• K1, K2, K3, and K4 are independently selected from the group consisting of N, O, S, Se, Te, and CH;
• S1, S2, S3, S4, S5, S6, S8, S9, S10, S11, S12, and S14 are independently selected from the group consisting of H, aryl, phenyl, alkyl, cycloalkyl, spiroalkyl, alkenyl, alkynyl, halogen, alkoxy, alkylthio, perfluoroalkyl, perfluoroaryl, pyridyl, cyano, thiocyanato, nitro, amino, alkylamino, acyl, sulfoxyl, sulfonyl, imido, amido, and carbamoyl;
• wherein S7 and S13 are together ═O;
• and wherein either (i) S1 and S5 are trans-substituted linking groups Q1 and Q2, (ii) S2 and S6 are trans-substituted linking groups Q1 and Q2, (iii) S10 and S12 are trans-substituted linking groups Q1 and Q2, or (iv) S9 and S11 are trans-substituted linking groups Q1 and Q2;
• and
• Q1 and Q2 are independently selected linking groups of the formula:
• wherein:
• n is from 0 or 1 to 5 or 10;
• R3 may be present or absent;
• R1, R2, and R3 are each independently selected from the group consisting of ethene, ethyne, aryl, and heteroaryl groups, which aryl and heteroaryl groups may be unsubstituted or substituted one or more times with H, aryl, phenyl, cycloalkyl, alkyl, alkenyl, alkynyl, halogen, alkoxy, alkylthio, perfluoroalkyl, perfluoroaryl, pyridyl, cyano, thiocyanato, nitro, amino, alkylamino, acyl, sulfoxyl, sulfonyl, imido, amido, and carbamoyl;
• and
• Y is a protected or unprotected reactive substituent selected from the group consisting of hydroxy, thio, seleno, telluro, ester, carboxylic acid, boronic acid, phenol, silane, sulfonic acid, phosphonic acid, alkylthiol, formyl, halo, alkenyl, alkynyl, haloalkyl, dialkyl phosphonate, alkyl sulfonate, acetylacetone, and dialkyl boronate groups.