Room-temperature synthesis of phthalocyanines (pcs) by condensation of phthalonitriles in the presence of solid sodium methoxide in THF is proposed for the synthesis of metal-free pcs with temperature- and/or base-sensitive substituents. The addition of metal salts after metal-free pc formation in the same vessel produces metallopcs in moderate to high (ca. 30–90%) yields.
The reaction of zinc tetrakis(3-pyridyloxy)phthalocyanine (1) with NH 4[ PtNH 3 Cl 3] leads to zinc tetrakis(cis-[3-oxypyridyl]-N]amminedichloroplatinum(II))phthalocyanine (2), while the reaction of 1 with cis- Pt ( DMSO )2 Cl 2 or 2 with DMSO forms zinc tetrakis(cis-[(3-oxypyridyl)-N]dichloro[sulfinylbis(methane)-S]platinum (II))phthalocyanine (3). The new phthalocyanines 2 and 3, with potentially combined photodynamic activity and cytotoxicity, have been characterized by means of electronic, 1 H NMR and IR spectroscopies.
The Solid Phase, Room-Temperature Synthesis of Particularly of 2,3,9,10,16,17,23,Octacyanophthalocyanines.-The condensation of phthalonitriles in the presence of sodium methoxide leads to metal-free phthalocyanines (pc). Furthermore, the one-pot addition of metal salt after pc formation produces the metallophthalocyanines, e.g.(III) and (IV). This room temperature pc-synthesis in THF has several advantages over previously known methods. - (NEMYKIN, VICTOR N.; KOBAYASHI, NAGAO; MYTSYK, VLADISLAV M.; VOLKOV, SERGEY V.; Chem. Lett. (2000) 5, 546-547; Dep. Chem., Grad. Sch. Sci., Tohoku Univ., Aoba, Sendai 980, Japan; EN)
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