Influence of Acid Catalyst on the Synthesis of trans-Porphyrins and Crystal Structure of a 5-(Pyren-1-yl)dipyrromethane

A family of trans-porphyrins (A(2)B(2), A(2)BC and A(2)C(2)), including fewer fused cyclic aromatics, was synthesized using 5-mesityldipyrromethane under negligible scrambling reaction conditions in high yields (15-48 %) with BF3(OEt2)/EtOH relative to that in trifluoroacetic acid (12-22 %) in CHCl3. The push-pull trans-A(2)BC, Zn(II)-carboxy porphyrins were prepared from their ester porphyrins and examined their fluorescence and electrochemical redox properties. In addition, the synthesis and single-crystal X-ray structure of a 5-(pyren-1-yl)dipyrromethane are also reported.