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Expanded porphyrins

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Macrocycles

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 161))

Abstract

Although considerable effort has been devoted to the synthesis and study of porphyrins and other tetrapyrrolic macrocycles, larger aromatic pyrrole-containing systems, the so-called “expanded porphyrins”, have received considerably less attention. Such systems, by virtue of containing a greater number of π electrons, a greater number of donating (e.g. pyrrolic) groups, or a larger central binding core, however, might have properties which differ substantially from their far better studied porphyrin analogues. In this review, the synthesis and properties of various large, pyrrole-, furan-, and thiopene-containing macrocycles will be discussed and the aromaticity properties of several of the better known expanded porphyrins, namely the sapphyrins, superphthalocyanines, pentaphyrins, texaphyrins, and vinylogous porphyrin-like annulenes, highlighted. In addition, to the extent they are known, the metal binding properties of the various “expanded” pyrrolic systems will be discussed and reviewed in terms of such variables as core size, donor number, and ligand geometry. Potential applications of the expanded porphyrins will also be presented with the use of certain systems as possible gadolinium (III) chelating agents for use in magnetic resonance imaging enhancement and as far-red absorbing photosensitizers for use in photodynamic therapy detailed. Opportunities for further work, both in regards to these potential applications and in terms of general expanded porphyrin chemical development, will also be presented.

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  1. Department of Chemistry and Biochemistry, University of Texas at Austin, 78712, Austin, Texas, USA

    Jonathan L. Sessler & Anthony K. Burrell

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© 1992 Springer-Verlag

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Sessler, J.L., Burrell, A.K. (1992). Expanded porphyrins. In: Macrocycles. Topics in Current Chemistry, vol 161. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3-540-54348-1_10

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  • DOI: https://doi.org/10.1007/3-540-54348-1_10

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