Triptycene Diols: A Strategy for Synthesizing Planar pi Systems through Catalytic Conversion of a Poly(p-phenylene ethynylene) into a Poly(p-phenylene vinylene)

Author(s)
Swager, Timothy Manning; Vanveller, Brett Steven; Robinson, Dale
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Abstract
At level best: A strategic synthesis of a new class of poly(p-phenylene vinylene)-bearing annulated alkene units from a parent poly(p-phenylene ethynylene) is described (see scheme). The gold-mediated cycloisomerization reaction of alkynes with appended hydroxy-group reacting partners delivers products having a stark increase in chain rigidity and planarity, as evidenced by pronounced photophysical changes.
Date issued
2011-12
URI
http://hdl.handle.net/1721.1/74226
Department
Massachusetts Institute of Technology. Department of Chemistry
Journal
Angewandte Chemie International Edition
Publisher
Wiley Blackwell
Citation
VanVeller, Brett, Dale Robinson, and Timothy M. Swager. “Triptycene Diols: A Strategy for Synthesizing Planar π Systems Through Catalytic Conversion of a Poly(p-phenylene Ethynylene) into a Poly(p-phenylene Vinylene).” Angewandte Chemie International Edition 51.5 (2012): 1182–1186.
Version: Author's final manuscript
ISSN
1433-7851
1521-3773
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