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Fully Aromatic High Performance Thermoset via Sydnone–Alkyne Cycloaddition

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Mitsubishi Chemical Center for Advanced Materials, §Department of Chemistry and Biochemistry, Materials Department, and Materials Research Laboratory, University of California, Santa Barbara, California 93106, United States
Mitsubishi Chemical USA, Inc., Chesapeake, Virginia 23320, United States
# Mitsubishi Chemical Group Science and Technology Research Center, Inc., Yokohama 227-8502, Japan
Institute of Pharmacy, Freie Universität Berlin, Königin-Luise-Str. 2-4, 14195 Berlin, Germany
Cite this: J. Am. Chem. Soc. 2016, 138, 20, 6400–6403
Publication Date (Web):May 16, 2016
https://doi.org/10.1021/jacs.6b03381
Copyright © 2016 American Chemical Society

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    Abstract

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    We have developed an efficient synthetic platform for the preparation of a new class of high performance thermosets based on the 1,3-dipolar cycloaddition of a bifunctional sydnone with a trifunctional alkyne. These processable materials possess outstanding thermal stability, with Td5% of 520 °C and a weight loss of <0.1% per day at 225 °C (both in air). Key to this performance is the stability of the starting functional groups that allows for reactive B-staging via simple thermal activation to give fully aromatic and highly cross-linked polypyrazole-based thermosets.

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