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

Hesheng Tang; Zemin Dong; Zul Merican; Davor Margetic; Zaljko Marinic; Maxwell J Gunter; David Officer; Douglas Butler; Ronald Warrener

doi:10.1016/j.tetlet.2008.11.109

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

Hesheng Tang, Zemin Dong, Zul Merican, Davor Margetic, Zaljko Marinic, Maxwell J Gunter, David Officer, Douglas Butler, Ronald Warrener

Research output: Contribution to journal › Article › peer-review

19 Citations (Scopus)

Abstract

Norbornene building BLOCKs formed by the reaction of porphyrin 1,3-dienes with norbornadiene or dimethyl tricyclo[4.2.1.02,5]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.

Original language	English
Pages (from-to)	667-670
Journal	Tetrahedron Letters
Volume	50
Issue number	6
DOIs	https://doi.org/10.1016/j.tetlet.2008.11.109
Publication status	Published - 2009

Keywords

Nanochemistry and Supramolecular Chemistry

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https://hdl.handle.net/1959.11/7817

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title = "Hinged bis-porphyrin scaffolds I: The synthesis of a new porphyrin diene and its role in constructing hinged porphyrin dyads and cavity systems",

abstract = "Norbornene building BLOCKs formed by the reaction of porphyrin 1,3-dienes with norbornadiene or dimethyl tricyclo[4.2.1.02,5]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.",

keywords = "Nanochemistry and Supramolecular Chemistry",

author = "Hesheng Tang and Zemin Dong and Zul Merican and Davor Margetic and Zaljko Marinic and Gunter, \{Maxwell J\} and David Officer and Douglas Butler and Ronald Warrener",

year = "2009",

doi = "10.1016/j.tetlet.2008.11.109",

language = "English",

volume = "50",

pages = "667--670",

journal = "Tetrahedron Letters",

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T1 - Hinged bis-porphyrin scaffolds I

T2 - The synthesis of a new porphyrin diene and its role in constructing hinged porphyrin dyads and cavity systems

AU - Tang, Hesheng

AU - Dong, Zemin

AU - Merican, Zul

AU - Margetic, Davor

AU - Marinic, Zaljko

AU - Gunter, Maxwell J

AU - Officer, David

AU - Butler, Douglas

AU - Warrener, Ronald

PY - 2009

Y1 - 2009

N2 - Norbornene building BLOCKs formed by the reaction of porphyrin 1,3-dienes with norbornadiene or dimethyl tricyclo[4.2.1.02,5]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.

AB - Norbornene building BLOCKs formed by the reaction of porphyrin 1,3-dienes with norbornadiene or dimethyl tricyclo[4.2.1.02,5]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.

KW - Nanochemistry and Supramolecular Chemistry

UR - https://www.scopus.com/pages/publications/57749190790

U2 - 10.1016/j.tetlet.2008.11.109

DO - 10.1016/j.tetlet.2008.11.109

M3 - Article

SN - 0040-4039

VL - 50

SP - 667

EP - 670

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 6

ER -

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

Abstract

Keywords

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