Evidence map›Paper›PMID 38418536›Full record

ArticleNature chemistry2024

Photoinduced dual bond rotation of a nitrogen-containing system realized by chalcogen substitution.

Shotaro Nagami, Rintaro Kaguchi, Taichi Akahane, Yu Harabuchi, Tohru Taniguchi, Kenji Monde, Satoshi Maeda, Satoshi Ichikawa, Akira Katsuyama

Abstract read
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In one paragraph

Article in Nature chemistry, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.

0numbers the graph read from it
0cells of the map it votes in
7citing papers in PubMed
–field-weighted citation impact
1 · What the graph read from it

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.

2 · The registry

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.

3 · Its place in the literature

Who cites it

7 citing papers in PubMed.

  1. Article
  2. Dihydrobenzofuro[3,2-Chemical science · 2026
    Article
  3. Article
  4. Multistate photoswitches beyond on and off.Nature communications · 2026
    Review
  5. Article
  6. Article
  7. pH-Controlled isomerization kinetics ofBeilstein journal of organic chemistry · 2025
    Article
4 · The record

Corrections and comments

PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.

5 · Who and what money

Authors and funding

9 authors.

Shotaro NagamiFaculty of Pharmaceutical Sciences, Hokkaido University, Sapporo, Japan.ORCID http://orcid.org/0000-0002-1665-1786
Rintaro KaguchiFaculty of Pharmaceutical Sciences, Hokkaido University, Sapporo, Japan.ORCID http://orcid.org/0000-0002-0719-4982
Taichi AkahaneFaculty of Pharmaceutical Sciences, Hokkaido University, Sapporo, Japan.ORCID http://orcid.org/0009-0003-8440-1687
Yu HarabuchiInstitute for Chemical Reaction Design and Discovery (WPI-ICReDD), Hokkaido University, Sapporo, Japan.ORCID http://orcid.org/0000-0001-8313-3236
Tohru TaniguchiFrontier Research Center of Advanced Material and Life Science, Faculty of Advanced Life Science, Hokkaido University, Sapporo, Japan.
Kenji MondeFrontier Research Center of Advanced Material and Life Science, Faculty of Advanced Life Science, Hokkaido University, Sapporo, Japan.ORCID http://orcid.org/0000-0002-1424-1054
Satoshi MaedaInstitute for Chemical Reaction Design and Discovery (WPI-ICReDD), Hokkaido University, Sapporo, Japan.ORCID http://orcid.org/0000-0001-8822-1147
Satoshi IchikawaFaculty of Pharmaceutical Sciences, Hokkaido University, Sapporo, Japan. ichikawa@pharm.hokudai.ac.jp.ORCID http://orcid.org/0000-0001-5345-5007
Akira KatsuyamaFaculty of Pharmaceutical Sciences, Hokkaido University, Sapporo, Japan. katsuyama@pharm.hokudai.ac.jp.ORCID http://orcid.org/0000-0002-4062-5561

Funding

Japan Agency for Medical Research and Development (AMED) JP22ama121039MEXT | Japan Science and Technology Agency (JST) JST-FORESTMEXT | Japan Society for the Promotion of Science (JSPS) 22K19002MEXT | Japan Society for the Promotion of Science (JSPS) JP18K19384MEXT | JST | Exploratory Research for Advanced Technology (ERATO) JPMJER1903
6 · The paper itself

Abstract

Photoinduced concerted multiple-bond rotation has been proposed in some biological systems. However, the observation of such phenomena in synthetic systems, in other words, the synthesis of molecules that undergo photoinduced multiple-bond rotation upon photoirradiation, has been a challenge in the photochemistry field. Here we describe a chalcogen-substituted benzamide system that exhibits photoinduced dual bond rotation in heteroatom-containing bonds. Introduction of the chalcogen substituent into a sterically hindered benzamide system provides sufficient kinetic stability and photosensitivity to enable the photoinduced concerted rotation. The presence of two different substituents on the phenyl ring in the thioamide derivative enables the generation of a pair of enantiomers and E/Z isomers. Using these four stereoisomers as indicators of which bonds are rotated, we monitor the photoinduced C-N/C-C concerted bond rotation in the thioamide derivative depending on external stimuli such as temperature and photoirradiation. Theoretical calculations provide insight on the mechanism of this selective photoinduced C-N/C-C concerted rotation.

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Registered trials

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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.