ArticleNature chemistry2012
A switching cascade of hydrazone-based rotary switches through coordination-coupled proton relays.
Article in Nature chemistry, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 32 papers.
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Who cites it
32 citing papers in PubMed, 182 citations in OpenAlex.
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- Solid-State Emissive Metallo-Supramolecular Assemblies of Quinoline-Based Acyl Hydrazone.Sensors (Basel, Switzerland) · 2020Article
- Using multiple self-sorting for switching functions in discrete multicomponent systems.Beilstein journal of organic chemistry · 2020Review
- Shape-Persistent Actuators from Hydrazone Photoswitches.Journal of the American Chemical Society · 2019Article
- Remote electrochemical modulation of pKProceedings of the National Academy of Sciences of the United States of America · 2018Article
- New molecular switch architectures.Proceedings of the National Academy of Sciences of the United States of America · 2018Article
- Selective Anion Extraction and Recovery Using a FeAngewandte Chemie (International ed. in English) · 2018Article
- A complementary pair of enantioselective switchable organocatalysts.Chemical science · 2017Article
- Article
- Redox Control over Acyl Hydrazone Photoswitches.Journal of the American Chemical Society · 2017Article
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- Quantification of Stereochemical Communication in Metal-Organic Assemblies.Angewandte Chemie (Weinheim an der Bergstrasse, Germany) · 2016Article
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4 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Imidazole, a subunit of histidine, plays a crucial role in proton-relay processes that are important for various biological activities, such as metal efflux, viral replication and photosynthesis. We show here how an imidazolyl ring incorporated into a rotary switch based on a hydrazone enables a switching cascade that involves proton relay between two different switches. The switching process starts with a single input, zinc(II), that initiates an E/Z isomerization in the hydrazone system through a coordination-coupled proton transfer. The resulting imidazolium ring is unusually acidic and, through proton relay, activates the E/Z isomerization of a non-coordinating pyridine-containing hydrazone switch. We hypothesize that the reduction in the acid dissociation constant of the imidazolium ring results from a combination of electrostatic and conformational effects, the study of which might help elucidate the proton-coupled electron-transfer mechanism in photosynthetic bacteria.
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