New functionalized C3-cyclotriveratrylenes bearing iodide groups at the periphery of the ring system were synthesized from the corresponding C3-tris(amino)-tris(methoxy)derivative (+/-)-3. On reaction with HNO 2 and KI, (+/-)-3 afforded (+/-)-5, which in turn was demethylated (BBr 3 ) to the triphenol (+/-)-6. Resolution of (+/-)-6 was effected by chromatographic separation of the diastereoisomeric triesters 9 obtained from this triphenol andR -(+)-2-(4-chlorophenoxy)propionic acid 8 as the resolving agent. The resolved (+) and (-)-6 were eventually converted to (+) and (-)-5, respectively, on methylation, and (+)-6 on reaction with acetic anhydride gave the triacetate (+)-10. The absolute configuration of 5 was established to be M-(+) by chemical transformation to the known P-(-)-cyclotrianisylene7 . Thus, all (+)-enantiomers of 5, 6, and 10 have M absolute stereochemistry. The inversion barrier of the cyclotriveratrylene ring in 6 was calculated to be ΔG < > 2 9 8 114.9 +/- 0.4 kJ mol - 1 from its racemization rate. Finally, the circular dichroism spectra of 5 and 6 were analyzed in the light of the exciton theory. It was concluded that the spectroscopic moment of the iodide group was smaller in magnitude than that of the CH 3 O or OH groups for the 1 L b transition of the benzene ring.