WATER-SOLUBLE PHTHALOCYANINES CONTAINING AZA-CROWN ETHER SUBSTITUENTS

A straightforward and generalizable synthesis of metal-free and metal (Ni, Pb, Lu) derivatives of symmetrically tetrasubstituted phthalocyanines derived from 15,16-dibromo- or -dicyano-2,3,6,7,8,9,11,12-octahydro-5H-benzo[e][1,4,7,13]tetroxazacyclopentadecine (1) is described. Quaternarization of the N-acetyl derivatives 7 in a chloroform/dimethyl sulfate mixture gives phthalocyanines 9 soluble in the pH range of 1 - 13. The electronic spectra of the phthalocyanines in buffered solutions (pH 4, 7, and 10) are examined. Furthermore, the electronic spectra of lutetium bis(phthalocyaninate) 9 d in water and in DMSO are compared for the first time.