ArticleChemical science2018
Photolabile coumarins with improved efficiency through azetidinyl substitution.
Article in Chemical science, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 27 papers.
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
27 citing papers in PubMed.
- Article
- Caged Monomethyl Auristatin F (MMAF) for Cell-Specific Activation Using a 488-nm-Optimized Photolabile Group.JACS Au · 2026Article
- Optimized Xanthenium Photocages with Fused Ring Systems for Photoactivated Chemotherapy and G Protein-Coupled Receptor Photopharmacology.Journal of the American Chemical Society · 2026Article
- Article
- Printed photonic crystal biochips for rapid and sensitive detection of biomarkers in various body fluids.Nature protocols · 2025Review
- Photocleavable Systems for Cell Biology: Conceptual Design across Molecular Modalities.Chembiochem : a European journal of chemical biology · 2025Review
- Orthogonal and Multiresponsive Quinolinone Systems for Reversible and Recyclable Polymer Networks.Journal of the American Chemical Society · 2025Article
- Breaking Bonds with Short-Wave Infrared Light: BODIPY Photocages for Two-Photon Activation in the 900-1500 nm NIR-II Window.Journal of the American Chemical Society · 2025Article
- Fluorogenic Coumarins Activated via Bioorthogonal Reactions.The Journal of organic chemistry · 2025Article
- Remote Silyl Groups Enhance Hydrolytic Stability and Photocleavage Efficiency in Carbamates for Protein Release.Angewandte Chemie (International ed. in English) · 2025Article
- Highly efficient CaOrganic & biomolecular chemistry · 2024Article
- Elucidating and Optimizing the Photochemical Mechanism of Coumarin-Caged Tertiary Amines.Journal of the American Chemical Society · 2024Article
- The fate of the contact ion pair determines the photochemistry of coumarin-based photocleavable protecting groups.Chemical science · 2024Article
- Exploring Structure-Activity Relationships in Photodynamic Therapy Anticancer Agents Based on Ir(III)-COUPY Conjugates.Journal of medicinal chemistry · 2023Article
- Inactivation of Competitive Decay Channels Leads to Enhanced Coumarin Photochemistry.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Synthesis, Optical Characterization in Solution and Solid-State, and DFT Calculations of 3-Acetyl and 3-(1'-(2'-Phenylhydrazono)ethyl)-coumarin-(7)-substituted Derivatives.Molecules (Basel, Switzerland) · 2022Article
- Rethinking Uncaging: A New Antiaromatic Photocage Driven by a Gain of Resonance Energy.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- Quadrupolar Dyes Based on Highly Polarized Coumarins.Organic letters · 2021Article
- Polarized Helical Coumarins: [1,5] Sigmatropic Rearrangement and Excited-State Intramolecular Proton Transfer.The Journal of organic chemistry · 2021Article
- Selective Modification for Red-Shifted Excitability: A Small Change in Structure, a Huge Change in Photochemistry.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
Corrections and comments
PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.
Authors and funding
6 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Azetidinyl substituents have been recently used to improve the fluorescence quantum yield of several classes of fluorophores. Herein, we demonstrate that other useful photochemical processes can be modulated using this strategy. In particular, we prepared and measured the quantum yield of photorelease of a series of 7-azetidinyl-4-methyl coumarin esters and compared it to their 7-diethylamino and julolidine-fused analogues. The efficiency of the photorelease reactions of the azetidinyl-substituted compounds was 2- to 5-fold higher than the corresponding diethylamino coumarins. We investigated the origin of this effect in model fluorophores and in the photoactivatable esters, and found that H-bonding with the solvent seems to be the prominent deactivation channel inhibited upon substitution with an azetidinyl ring. We anticipate that this substitution strategy could be used to modulate other photochemical processes with applications in chemical biology, catalysis and materials science.
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.