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An efficient two-step synthesis of metal-free phthalocyanines using a Zn(II) template


Alzeer, J; Roth, P J C; Luedtke, N W (2009). An efficient two-step synthesis of metal-free phthalocyanines using a Zn(II) template. Chemical Communications, (15):1970-1971.

Abstract

The templating effects of strongly coordinating ions like Co(II), Cu(II), and Zn(II) can dramatically improve the yields of phthalocyanine synthesis. The main problem with this approach is the lack of reported conditions for the subsequent removal of such ions to generate metal-free phthalocyanines. During our synthesis of guanidine-containing phthalocyanines we discovered a new demetallation reaction that, to the best of our knowledge, provides the first examples of Zn(II) removal without destroying the phthalocyanine itself. This demetallation reaction appears to be general as it works for electron rich, electron poor, and unsubstituted phthalocyanines. Zn(II)-templated cyclotetramerization, followed by Zn(II) removal provides a high-yielding route (80 – 90 %) to diverse, metal-free phthalocyanines. In contrast, the reported yields with existing methods are typically 10 – 60 %. Given the general importance of metal-free phthalocyanines in photovoltaic devices, chemical sensors, and data storage devices, we are confident this new route to metal-free phthalocyanines will be of general interest.

Abstract

The templating effects of strongly coordinating ions like Co(II), Cu(II), and Zn(II) can dramatically improve the yields of phthalocyanine synthesis. The main problem with this approach is the lack of reported conditions for the subsequent removal of such ions to generate metal-free phthalocyanines. During our synthesis of guanidine-containing phthalocyanines we discovered a new demetallation reaction that, to the best of our knowledge, provides the first examples of Zn(II) removal without destroying the phthalocyanine itself. This demetallation reaction appears to be general as it works for electron rich, electron poor, and unsubstituted phthalocyanines. Zn(II)-templated cyclotetramerization, followed by Zn(II) removal provides a high-yielding route (80 – 90 %) to diverse, metal-free phthalocyanines. In contrast, the reported yields with existing methods are typically 10 – 60 %. Given the general importance of metal-free phthalocyanines in photovoltaic devices, chemical sensors, and data storage devices, we are confident this new route to metal-free phthalocyanines will be of general interest.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:2009
Deposited On:05 Jan 2010 11:43
Last Modified:05 Apr 2016 13:41
Publisher:Royal Society of Chemistry
ISSN:1359-7345
Publisher DOI:https://doi.org/10.1039/b822985f
PubMed ID:19333460

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