A systematic approach to the synthesis of σ-organometallophthalocyanines is described. Structurally characterized σ-organoPcM complexes are presented, including the first PcCr-aryl, PcCr-alkynyl, and PcCr-Wittig complexes - representing the first examples of these classes of complexes for any metallophthalocyanine - and the first PcCr-alkyl complexes, which span three chromium and two Pc-ring oxidation states. This represents a rational marriage of the broad organometallic and phthalocyanine fields, opening the door for the exploration of this classical, stable, redox-active macrocycle as an ancillary ligand in metal-carbon chemistry.
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