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Title: Establishing a library of porphyrin building blocks for superstructured assemblies: porphyrin dienes and dienophiles for cycloaddition reactions
Contributor(s): Gunter, Maxwell John (author); Tang, Hesheng (author); Warrener, RN (author)
Publication Date: 2002
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Abstract: The synthesis and utility of a series of porphyrins with (masked) diene and dienophile functionality are described. The key porphyrin diene is synthesised from a sulfolenopyrrole by a 3+1 strategy. A range of Diels-Alder cycloadducts is readily accessed from the diene by mild thermal extrusion of sulfur dioxide from the sulfolenoporphyrin, which produces the reactive porphodimethylidene. Each of these cycloadducts is fused to the porphyrin nucleus through a cyclohexene ring thus retaining some conformational flexibility in the resultant structures. The structures can be rigidified by mild oxidation to the corresponding benzo-derivatives. Diels-Alder reaction of the porphyrin 1,3-diene resulting from the sulfolenoporphyrin with norbornadiene produces the norbornene derivative, which can serve as a dienophile or dipolarophile in subsequent cycloaddition reactions. Nevertheless, a preferred route to this structure is through a corresponding 1+3 route, where the norbornene component is part of the tripyrrane. Extension of the synthetic protocols allows ready access to a "mixed function" porphyrin, containing both diene and dienophile components. Likewise, the synthesis of a bis-norbornene porphyrin is described. A collection of each of these reactive components is the basis for a library of building blocks which allows easy and simple entry to a wide variety of complex porphyrin-containing superstructures.
Publication Type: Journal Article
Source of Publication: Journal of Porphyrins and Phthalocyanines, v.6 (11), p. 673
Publisher: World Scientific Publishing Co Pte Ltd
Place of Publication: Singapore
ISSN: 1088-4246
Field of Research (FOR): 030302 Nanochemistry and Supramolecular Chemistry
Peer Reviewed: Yes
HERDC Category Description: C1 Refereed Article in a Scholarly Journal
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