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

Tanga, Hesheng, Dong, Zemin, Merican, Zul, Margetić, Davor, Marinić, Željko, Gunter, Maxwell J., Officer, David, Butler, Douglas N. and Warrener, Ronald N. (2009) Hinged bis-porphyrin scaffolds I. The synthesis of a new porphyrin diene and its role in constructing hinged porphyrin dyads and cavity systems. Tetrahedron Letters, 50 6: 667-670. doi:10.1016/j.tetlet.2008.11.109


Author Tanga, Hesheng
Dong, Zemin
Merican, Zul
Margetić, Davor
Marinić, Željko
Gunter, Maxwell J.
Officer, David
Butler, Douglas N.
Warrener, Ronald N.
Title Hinged bis-porphyrin scaffolds I. The synthesis of a new porphyrin diene and its role in constructing hinged porphyrin dyads and cavity systems
Journal name Tetrahedron Letters   Check publisher's open access policy
ISSN 0040-4039
1873-3581
Publication date 2009-02-11
Sub-type Article (original research)
DOI 10.1016/j.tetlet.2008.11.109
Open Access Status Not yet assessed
Volume 50
Issue 6
Start page 667
End page 670
Total pages 4
Place of publication Oxford, U.K.
Publisher Pergamon Press
Language eng
Subject 0305 Organic Chemistry
Formatted 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.
© 2008 Elsevier Ltd. All rights reserved.
Keyword Molecular tweezers
Cyclic dimer
Cycloaddition
Host
Alkenes
Chemistry
Framework
Binding
Energy
Wires
Q-Index Code C1
Q-Index Status Provisional Code

 
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