5-(4-Iodophenyl)-l,9-dimethyldipyrromethane ua). This condensation follows nearly the same
conditions employed for forming meso-porphyrins (29). In a 1 L one-neck round bottom flask with a stir
bar was placed 2-methylpyrrole (35) (648 mg, 8 mmol), 44odobenzaldehyde (928 mg, 4 mmol), and 800
mL CH2C12. The clear solution was purged with Ar for 30 min. Trifluoroacetic acid (62 pL, 0.8 mmol,
10-3 M) was added to initiate the condensation. After 1.5 h TLC (silica, CH2C12) showed that all of the
aldehyde had been consumed. The light yellow reaction mixture was then washed with 100 mL of 0.1 N
NaOH, 200 mL of H20, dried (NqSOq), filtered, and rotary evaporated to a viscous green oil. The oil was
quickly placed on a vacuum line to remove residual solvent and prevent decomposition. A light green solid
(1.44 g) was immediately obtained (95% yield). *H NMR (CDC13) 6 2.20 (s, 6 H, CH3), 5.28 (s, 1 H,
CH), 5.76 (d, 4 H, p-pyrrole), 7.00 (AA'BB', 2 H, ArH), 7.60 (AABB', 2 H, ArH).

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