TY - JOUR
T1 - Syntheses of Monometalated and Unsymmetrically Substituted Binuclear Phthalocyanines and a Pentanuclear Phthalocyanine by Solution and Polymer Support Methods
AU - Leznoff, Clifford C.
AU - Svirskaya, Polina I.
AU - Khouw, Ben
AU - Seymour, Penny
AU - Lever, A. B.P.
AU - Cerny, Ronald L.
PY - 1991/1/1
Y1 - 1991/1/1
N2 - Binuclear phthalocyanines in which two different phthalocyanine nuclei are covalently linked through five-atom bridges, derived from 2-ethyl-2-methylpropane-1,3-diol, are prepared. In the examples, one phthalocyanine ring is always substituted with neopentoxy substituents, while the other phthalocyanine ring is unsubstituted or contains tert-butyl substituents or a neopentoxy-substituted copper phthalocyanine, constituting a binuclear phthalocyanine in which only one ring is metalated. The precursor, 2-(2-(hydroxymethyl)-2-methylbutoxy)-9, 16, 23-trineopentoxyphthalocyanine was prepared in solution and also by solid-phase methods, using polymer-bound trityl chloride derived from a 1 % divinylbenzene-co-styrene copolymer. A metal-free pentanuclear phthalocyanine, in which four phthalocyaninyl groups are covalently bound to the four benzo groups of a central phthalocyanine nucleus, is described and characterized by FAB mass spectroscopy. In some experiments some rare examples of demetalation of some zinc phthalocyanines are noted during phthalocyanine formation. A modified flash chromatography procedure proved to be useful for separating similarly substituted mononuclear phthalocyanines.
AB - Binuclear phthalocyanines in which two different phthalocyanine nuclei are covalently linked through five-atom bridges, derived from 2-ethyl-2-methylpropane-1,3-diol, are prepared. In the examples, one phthalocyanine ring is always substituted with neopentoxy substituents, while the other phthalocyanine ring is unsubstituted or contains tert-butyl substituents or a neopentoxy-substituted copper phthalocyanine, constituting a binuclear phthalocyanine in which only one ring is metalated. The precursor, 2-(2-(hydroxymethyl)-2-methylbutoxy)-9, 16, 23-trineopentoxyphthalocyanine was prepared in solution and also by solid-phase methods, using polymer-bound trityl chloride derived from a 1 % divinylbenzene-co-styrene copolymer. A metal-free pentanuclear phthalocyanine, in which four phthalocyaninyl groups are covalently bound to the four benzo groups of a central phthalocyanine nucleus, is described and characterized by FAB mass spectroscopy. In some experiments some rare examples of demetalation of some zinc phthalocyanines are noted during phthalocyanine formation. A modified flash chromatography procedure proved to be useful for separating similarly substituted mononuclear phthalocyanines.
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U2 - 10.1021/jo00001a019
DO - 10.1021/jo00001a019
M3 - Article
AN - SCOPUS:0001848241
SN - 0022-3263
VL - 56
SP - 82
EP - 90
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 1
ER -