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Two-Step Synthesis of Stable Dioxadicarbaporphyrins from Bis(3-indenyl)methane


  • Part 62 in the series “Conjugated Macrocycles Related to the Porphyrins”. This work was supported by the National Science Foundation (NSF) (CHE-0911699 and CHE-1212691) and the Petroleum Research Fund, administered by the American Chemical Society. The authors also thank the Youngstown State University Structure & Chemical Instrumentation Facility’s Matthias Zeller for X-ray data collection. The diffractometer was funded by the NSF (0087210), the Ohio Board of Regents (CAP-491), and YSU.


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Porphyrin without N: Bilin analogues and related aromatic dicarbaporphyrinoids have been prepared from bis(3-indenyl)methane. Even though all four pyrrole rings from the porphyrin macrocycle have been replaced by two furan and two indene subunits, the system retains porphyrin-like UV/Vis spectra and highly diatropic characteristics.