ArticleJournal of the American Chemical Society2025
Functionalized Terthiophene as an Ambipolar Redox System: Structure, Spectroscopy, and Switchable Proton-Coupled Electron Transfer.
Article in Journal of the American Chemical Society, 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 1 paper.
What it found
Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.
The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.
Who cites it
1 citing paper in PubMed.
- Feedstock-Derived Thiophene Radical Anions Exhibiting Redox Stability at Extreme Potentials.Angewandte Chemie (International ed. in English) · 2025Article
Corrections and comments
PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.
Authors and funding
4 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Organic redox systems that can undergo oxidative and reductive (ambipolar) electron transfer are elusive yet attractive for applications across synthetic chemistry and energy science. Specifically, the use of ambipolar redox systems in proton-coupled electron transfer (PCET) reactions is largely unexplored but could enable "switchable" reactivity wherein the uptake and release of hydrogen atoms are controlled using a redox stimulus. Here, we describe the synthesis and characterization of an ambipolar functionalized terthiophene (TTH) bearing methyl thioether and phosphine oxide groups that exhibits switchable PCET reactivity. Electrochemical studies established that the functionalized TTH can be reversibly oxidized and reduced, prompting the synthesis and characterization of cationic and anionic radicals on a single TTH platform. Combined structural, spectroscopic, and computational investigations revealed the influence of the methyl thioether and phosphine oxide moieties on the TTH electronic structure that results in the stabilization of both cationic and anionic radicals. Upon single-electron oxidation, the functionalized TTH serves as a hydrogen atom acceptor and undergoes PCET with 1,4-dihydroquinone to generate a TTH hydroxyphosphonium species. The process was found to be reversible upon single-electron reduction, with functionalized TTH acting as a hydrogen atom donor in a PCET reaction with 2,3-dimethylanthraquinone. The thermochemistry of the O-H bond formed and cleaved in functionalized TTH during the reaction sequence was investigated, revealing that a bond weakening of 30 kcal/mol underpins the switchable PCET reactivity. Overall, these studies provide an electrochemical, structural, spectroscopic, and thermochemical foundation for the use of ambipolarity to control PCET reactions in organic redox systems.
Identifiers
What OpenQuestion holds
Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.