Synthesis and Characterization of New Metal-free and Metallophthalocyanines Substituted with Tetrathiadiazamacrobicyclic Moieties

Abstract

New metal-free (5, 8) and metallophthalocyanines (6, 9) containing four diazatetrathiamacrobicycles or crosswise-disubstituted attached with two nitro and two macrobicyclic groups were synthesized by cyclotetramerization of 7,8-dicyano-4,11,22,23-tetrathia-1,14-diazapentacyclo[12.10.10.05,10.016,21.026,31]tetratriconta-5,7,12,19,20,21,28,30,32-nonane (3), 8,10-dihydro-8,11-diimino-4,14,24,34,-tetrathia-1,17-diazapentacyclo[15.13.13.05,13.019,23.028,33]tetratriconta-5,7,12,19,20,22,28,30,32-nonaisoiminoindoline (4) or 6-nitro-1,3,3-trichloroisoindolenine (7) in the presence of the corresponding metal salt or a strong organic base. The new compounds were characterized by a combination of elemental analysis and 1H NMR, 13C NMR, IR, UV–Vis and MS spectral data.