Evidence map›Paper›PMID 29732087›Full record

ArticleChemical science2018

Spironaphthoxazine switchable dyes for biological imaging.

Yaoyao Xiong, Andreas Vargas Jentzsch, Johannes W M Osterrieth, Erdinc Sezgin, Igor V Sazanovich, Katharina Reglinski, Silvia Galiani, Anthony W Parker, Christian Eggeling, Harry L Anderson

Erratum issuedOpen access · diamondAbstract read
In one paragraph

Article in Chemical science, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. An erratum has been issued. Cited by 19 papers.

0numbers the graph read from it
0cells of the map it votes in
19citing papers in PubMed
3.9field-weighted citation impact, top 5% of its field
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

19 citing papers in PubMed, 60 citations in OpenAlex.

  1. Photokinetics of Photothermal Reactions.Molecules (Basel, Switzerland) · 2025
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  12. Review
  13. Article
  14. A Chalcogen-Bonding Cascade Switch for Planarizable Push-Pull Probes.Angewandte Chemie (International ed. in English) · 2019
    Article
  15. Article
  16. Article
  17. Article
  18. Solution and Solid-State Emission Toggling of a Photochromic Hydrazone.Journal of the American Chemical Society · 2018
    Article
  19. Review
4 · The record

Corrections and comments

5 · Who and what money

Authors and funding

10 authors at 4 institutions in 4 countries.

Yaoyao XiongDepartment of Chemistry , University of Oxford , Chemistry Research Laboratory , Oxford OX1 3TA , UK . Email: harry.anderson@chem.ox.ac.uk.ORCID 0000-0002-3741-7454
Andreas Vargas JentzschDepartment of Chemistry , University of Oxford , Chemistry Research Laboratory , Oxford OX1 3TA , UK . Email: harry.anderson@chem.ox.ac.uk.ORCID 0000-0003-1386-3174
Johannes W M OsterriethDepartment of Chemistry , University of Oxford , Chemistry Research Laboratory , Oxford OX1 3TA , UK . Email: harry.anderson@chem.ox.ac.uk.
Erdinc SezginMRC Human Immunology Unit , Weatherall Institute of Molecular Medicine , University of Oxford , OX3 9DS , Oxford , UK.
Igor V SazanovichCentral Laser Facility , Research Complex at Harwell, Science and Technology Facilities Council , Harwell Campus , Didcot OX11 0QX , UK.
Katharina ReglinskiMRC Human Immunology Unit , Weatherall Institute of Molecular Medicine , University of Oxford , OX3 9DS , Oxford , UK.
Silvia GalianiMRC Human Immunology Unit , Weatherall Institute of Molecular Medicine , University of Oxford , OX3 9DS , Oxford , UK.
Anthony W ParkerCentral Laser Facility , Research Complex at Harwell, Science and Technology Facilities Council , Harwell Campus , Didcot OX11 0QX , UK.ORCID 0000-0003-3094-9762
Christian EggelingMRC Human Immunology Unit , Weatherall Institute of Molecular Medicine , University of Oxford , OX3 9DS , Oxford , UK.
Harry L AndersonDepartment of Chemistry , University of Oxford , Chemistry Research Laboratory , Oxford OX1 3TA , UK . Email: harry.anderson@chem.ox.ac.uk.ORCID 0000-0002-1801-8132
Oxfam · GBUniversity of Oxford · GBScience and Technology Facilities Council · GBLeibniz Institute of Photonic Technology · DE

Funding

Medical Research Council MC_UU_00008/9Medical Research Council MC_UU_12010/9Medical Research Council MR/K01577X/1Wellcome Trust
6 · The paper itself

Abstract

Recent developments in super-resolution microscopy have significantly expanded the requirements for switchable dyes, leading to demand for specially designed molecular switches. We report the synthesis and characterization of a spironaphthoxazine photochromic switch (a derivative of palatinate purple) displaying high photoconversion (85-95%) under readily accessible 405 nm light, broad absorption in the visible, and excellent fatigue resistance. The indole substituent on this spironaphthoxazine is twisted out of conjugation with the naphthalene unit, yet it is crucial for activation with visible light. The open colored merocyanine form of the spironaphthoxazine reverts to the closed form with a lifetime of 4.7 s in dichloromethane at 20 °C; this thermal reversion is even faster in more polar solvents. The photochemical quantum yields for ring-opening and ring-closing are approximately 8% and 1%, respectively, in dichloromethane. The ring-opening and ring-closing reactions have been characterized by time-resolved infrared and transient absorption spectroscopies. Ring opening occurs rapidly (

Identifiers

PMID29732087
PMCPMC5916019
OpenAlexW2788197191

What OpenQuestion holds

Textmetadata
LicenceCC BY
Read underepoch 390

Registered trials

None linked

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.