Syntheses of Monometalated and Unsymmetrically Substituted Binuclear Phthalocyanines and a Pentanuclear Phthalocyanine by Solution and Polymer Support Methods

Clifford C. Leznoff, Polina I. Svirskaya, Ben Khouw, Ronald L. Cerny, Penny Seymour, Ronald Cerny

Research output: Contribution to journalArticle

78 Citations (Scopus)

Abstract

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.

Original languageEnglish (US)
Pages (from-to)82-90
Number of pages9
JournalJournal of Organic Chemistry
Volume56
Issue number1
DOIs
StatePublished - Jan 1 1991

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Polymers
divinyl benzene
phthalocyanine
Chromatography
Metals
Spectroscopy
Atoms
Experiments

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Syntheses of Monometalated and Unsymmetrically Substituted Binuclear Phthalocyanines and a Pentanuclear Phthalocyanine by Solution and Polymer Support Methods. / Leznoff, Clifford C.; Svirskaya, Polina I.; Khouw, Ben; Cerny, Ronald L.; Seymour, Penny; Cerny, Ronald.

In: Journal of Organic Chemistry, Vol. 56, No. 1, 01.01.1991, p. 82-90.

Research output: Contribution to journalArticle

Leznoff, Clifford C. ; Svirskaya, Polina I. ; Khouw, Ben ; Cerny, Ronald L. ; Seymour, Penny ; Cerny, Ronald. / Syntheses of Monometalated and Unsymmetrically Substituted Binuclear Phthalocyanines and a Pentanuclear Phthalocyanine by Solution and Polymer Support Methods. In: Journal of Organic Chemistry. 1991 ; Vol. 56, No. 1. pp. 82-90.
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