Synthesis of a Bisdienophilic Phthalocyanine and of Precursors for Repetitive Diels-Alder Reactions Based on Hemiporphyrazines and Phthalocyanines

The specific synthesis of a metal‐free bisdienophilic phthalocyanine 193, suitable for repetitive Diels‐Alder reactions, is reported. This was achieved by condensation of 191,3,3‐trichloro‐6/7‐nitroioindolenine (191) and 4,9‐dibutoxy‐2,3,5,8‐tetrahydro‐1,3‐diimino‐1H‐5,8‐epoxybenz[f]isoindoline (2). The ability of 3 to undergo Diels‐Alder reactions was tested by reaction with an excess of 1,2,3,4‐tetraphenylcyclopentadienone (5). Experimental data of the hemiporphyrazines 9, 10, and 11, which can be used as precursors for the synthesis of ladder polymers, are also given in the Experimental Section.