4.8 Article

Waste Management of Chemically Activated Switches: Using a Photoacid To Eliminate Accumulation of Side Products

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 136, Issue 50, Pages 17438-17441

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ja511135k

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Funding

  1. National Science Foundation [CHE-1253385]
  2. American Chemical Society Petroleum Research Fund [51842-DNI4]
  3. Direct For Mathematical & Physical Scien
  4. Division Of Chemistry [1253385] Funding Source: National Science Foundation

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Molecular switches and machines that are powered by acid-base reactions are susceptible to low switching cycles because of the concomitant formation of waste products during their operation. Here, we demonstrate the fast, efficient, and reversible modulation of a hydrazone switch in methanol using a visible-light activated photoacid, with no generation of side products, high conversion rates (>95%), and no loss of activity over 100 cycles. TEG functionalization of the hydrazone switch allows for the process to be carried with high conversion (>90%) in water as well.

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