Ab icyclo[2.2.2]octadiene(BCOD)-fused bis(dipyrromethane) derivative was reacted with methylal in the presence of trifluoroacetic acid followed by oxidation with chloranil to give ad oubly N-confused phlorin derivative,w hich did not undergo the retro-Diels-Alder reaction extruding an ethylenem olecule on heating. In contrast, a7 -tert-butoxybicyclo[2.2.1]heptadiene(7-BuOBCHD)-fused bis(dipyrromethane) yieldedb enzene-ring-fused doubly N-confused porphyrins by following similar reaction sequences.[a] Prof.Supporting information (Experimental details,N MR spectra, and X-ray analysis data) and the ORCID identification number(s)for the author(s) of this articlecan be foundu nder:https://doi.Figure 7. ACID plot (left) and NICS(0)v alues(right) of 2a''.Inthe ACID plot, diamagnetic ring current paths are emphasized by blue lines with arrows. Bold bondsint he right drawing highlight two 18p macrocyclic pathways (black and magenta vs. black and green).
Benzene-fused bis(acenaphthoBODIPY)s prepared by retro-Diels–Alder reaction of bicyclo[2.2.2]octadiene-fused precursors showed strong absorption bands in the near-infrared region and very weak absorptions in the visible region.
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