First selective one-stage transformation of A4-to A3B- type Phthalocyanineстатья
Статья опубликована в высокорейтинговом журнале
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Аннотация:In this work, we show for the first time that low-symmetry phthalocyanines of A3B-type can be readily obtained in one stage from the corresponding symmetric alkoxy-substituted A4-type precursors by cleavage of a single ether bond. Namely, two 2,3,9,10,16,17,23,24-octa-n-butoxyphthalocyanines (BuOPcM, where M = 2H, Cu) were selectively transformed to the corresponding 2-hydroxy-3,9,10,16,17,23,24-hepta-n-butoxyphthalocyanine derivatives in acidic conditions. The selectivity of the ether bond cleavage largely depends on the temperature and time of action of sulfuric acid on toluene solutions of the starting A4-type compounds. The new method gives superior overall yields of A3B-type phthalocyanines (>70%) compared to the common approach, which implies statistical cyclization of two different phthalogens. The target compounds can be considered as precursors for polymacrocyclic structures, as well as the basis for optical materials.