Mechanochemical Synthesis of Extended Iptycenes
Name
Mechanochemical Synthesis of Extended Iptycenes.pdf
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198.31 KB
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Checksum (MD5)
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Author(s)
Zhao, Yanchuan
Veleirinho de Oliveira Rocha, Silvia
Swager, Timothy M
Date Issued
October 2016
Journal
Journal of the American Chemical Society
Publisher
American Chemical Society (ACS)
Citation
Zhao, Yanchuan et al. “Mechanochemical Synthesis of Extended Iptycenes.” Journal of the American Chemical Society 138, 42 (October 2016): 13834–13837 © 2016 American Chemical Society
Version
Author's final manuscript
Abstract
Iptycenes are intriguing compounds receiving considerable attention as a result of their rigid noncompliant three-dimensional architecture. The preparation of larger iptycenes is often problematic, as a result of their limited solubility and synthetic procedures involving multiple Diels–Alder reactions under harsh extended reaction conditions. We report a mechanochemical synthesis of structurally well-defined iptycenes through an iterative reaction sequence, wherein Diels–Alder reactions and a subsequent aromatization afford higher order iptycenes. We further report that double Diels–Alder reactions under solvent-free condition provide facile access to highly functionalized iptycenes with molecular weights over 2000 Da. Quartz crystal microbalance measurements reveal that these materials efficiently absorb the aromatic hydrocarbons benzene and toluene.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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Article is made available in accordance with the publisher's policy and may be subject to US copyright law. Please refer to the publisher's site for terms of use.
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DOI of Published Version
https://doi.org/10.1021/jacs.6b09011
