Hinged bis-porphyrin scaffolds I. The synthesis of a new porphyrin diene and its role in constructing hinged porphyrin dyads and cavity systems

Autor:	Zemin Dong, Ronald N. Warrener, David L. Officer, Hesheng Tang, Zul Merican, Maxwell J. Gunter, Davor Margetić, Douglas N. Butler, Željko Marinić
Rok vydání:	2009
Předmět:	Cyclobutene Diene Stereochemistry Norbornadiene Organic Chemistry Epoxide porphyrins cycloaddition Diels-Alder supramolecular Biochemistry Porphyrin Cycloaddition chemistry.chemical_compound chemistry Drug Discovery Molecular tweezers Norbornene
Zdroj:	Tetrahedron Letters. 50:667-670
ISSN:	0040-4039
DOI:	10.1016/j.tetlet.2008.11.109
Popis:	Norbornene building BLOCKs formed by the reaction of porphyrin 1,3-dienes with norbornadiene or dimethyl tricyclo[4.2.1.0 2,5 ]nona-2,7-diene-3,4-dicarboxylate were coupled with an ester-activated cyclobutene epoxide BLOCK to afford the first examples of hinged porphyrin-spacer-acceptor dyads. Similar dual coupling with a bis-(cyclobutene epoxide) formed doubly hinged POR-spacer-POR scaffolds separated by up to 16σ-bonds. The ability of the doubly hinged ZnPOR-16σ-ZnPOR scaffold to adopt cavity-shaped conformations was indicated by semiempirical AM1 calculations of these conformationally flexible bis-porphyrin scaffolds.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::8ab2b10405c0f81e0ea782e611c37cb8 https://doi.org/10.1016/j.tetlet.2008.11.109 Zobrazit plný text záznamu Full Text from ScienceDirect