Synthesis and Properties of Copper(II) Phthalocyanines with Monoazacrown and Crown Ethers as Peripheral Substituents

Abstract

Soluble and less soluble phthalocyaninatocopper(II) derivatives (4a and 4b) were prepared from the corresponding 7-[(4′-benzo-15-crown-5)oyl]-15, 16-dibromo-2,3,6,7,8,9,11,12-octahydro-5H-benzo[e]-[1,4,10,13,7] tetraoxaazacyclopentadecine (3a) and 7-(2′-tosylaminoethyl)-15, 16-dibromo-2,3,6,7,8,9,11, 12-octahydro-5H-benzo[e]-[1,4,10,13,7] tetraoxaazacyclopentadecine (3b) and CuCN in pyridine. A less soluble novel multifunctionalized scorpiand macrocycle-substituted phthalocyanine (4c) in which an NH2CH2CH2— chain is appended to a monoazacrown ether ring was obtained by detosylation of 4b with concentrated sulfuric acid.