Synthesis of meso -Unsubstituted and/or meso -Spiroadamantyl-Substituted Tetrapyrrole Macrocycles Scrambling Oligopyrrole Precursors into cis - and trans -Arranged Cyclic Arrays

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Abstract
Calix[4]pyrroles with unsubstituted meso-positions were synthesized by precipitating the products from reaction mixtures. The introduction of meso-spiroadamantyl subunits resulted in the scrambling of oligopyrrole intermediates during [2 + 2] condensation reactions. This process afforded a combination of cis- and trans-arranged isomers, as well as significant spectroscopic modifications arising from close contacts between the adjacent π-planes by the bulky adamantyl groups attached to the meso-positions in a spiro configuration.
Funding Information
  • Japan Society for the Promotion of Science (22K05081)
  • Japan Society for the Promotion of Science (25K08611)

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