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The conversion of meso-aryl-porphyrins/chlorins to porphyrinoids containing nonpyrrolic heterocycles (so-called pyrrole-modified porphyrins, PMPs) along an approach we dubbed "the breaking and mending of porphyrins" is well known. However, examples are limited to the synthesis of PMPs containing up to six-membered heterocycles; the syntheses of larger rings failed. We report here hitherto unavailable eight-membered chlorin-type PMPs using an inverted "mending and breaking" approach. All examples are based on the addition of N,N'-dimeth
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