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High-Yield, One-Step Synthesis of o-Phenylene Ethynylene Cyclic Trimer via Precipitation-Driven Alkyne Metathesis

Zhang, Wei and Brombosz, Scott M. and Mendoza, Jose L. and Moore, Jeffrey S. (2005) High-Yield, One-Step Synthesis of o-Phenylene Ethynylene Cyclic Trimer via Precipitation-Driven Alkyne Metathesis. Journal of Organic Chemistry, 70 (24). pp. 10198-10201. ISSN 0022-3263. https://resolver.caltech.edu/CaltechAUTHORS:20130528-132014449

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Abstract

A shape-persistent, conjugated o-phenylene ethynylene cyclic trimer was prepared in one step from tetrasubstituted benzene monomer 4 in 86% isolated yield through precipitation-driven alkyne metathesis. The template-free, selective generation of the molecular triangle 5 is a thermodynamically favored process and under equilibrium control. A novel tetrameric macrocycle 7 was generated via scrambling metathesis between tricycle 5 and hexacycle 6 using this dynamic covalent chemistry.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/jo0517803DOIUNSPECIFIED
http://pubs.acs.org/doi/abs/10.1021/jo0517803PublisherUNSPECIFIED
Additional Information:© 2005 American Chemical Society. Received August 23, 2005; Published In Issue November 25, 2005. This material is based upon work supported by the National Science Foundation under Grant No. 0345254 and the U.S. Department of Energy, Division of Materials Sciences, under Award No. DEFG02-91ER45439, through the Frederick Seitz Materials Research Laboratory at the University of Illinois at Urbana-Champaign.
Funders:
Funding AgencyGrant Number
NSF0345254
Department of Energy (DOE) Division of Materials SciencesDEFG02-91ER45439
Issue or Number:24
Record Number:CaltechAUTHORS:20130528-132014449
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20130528-132014449
Official Citation:A High-Yield, One-Step Synthesis of o-Phenylene Ethynylene Cyclic Trimer via Precipitation-Driven Alkyne Metathesis Wei Zhang,Scott M. Brombosz,†, Jose L. Mendoza,‡ and, and Jeffrey S. Moore* The Journal of Organic Chemistry 2005 70 (24), 10198-10201
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:38694
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:30 May 2013 19:35
Last Modified:03 Oct 2019 04:59

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