ArticleThe journal of physical chemistry. B2013
Characterization of the thermal and photoinduced reactions of photochromic spiropyrans in aqueous solution.
Article in The journal of physical chemistry. B, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 30 papers.
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Who cites it
30 citing papers in PubMed, 120 citations in OpenAlex.
- Molecular Engineering for Nonlinear Fluorescence: En Route to Three-Photon Absorption via Sequential One-Photon Excitation.Journal of the American Chemical Society · 2026Article
- Bridging light and sound: A spironaphtopyran-rhodamine dyad with high-contrast photoswitching between fluorescence and photoacoustic signal.Photoacoustics · 2026Article
- Optical Force Monitoring in Polymeric Materials with a Coumarin-Based Mechanophore.Angewandte Chemie (International ed. in English) · 2025Article
- Photoswitchable Merocyanine-Amphiphiles with Programmable Self-Assembly Times.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- Arylpyrrolylidene-indanones as readily synthesised photoswitches offering dual- and single-colour fluorescence toggling with nearly quantitativeChemical science · 2025Article
- Photoswitches beyond azobenzene: a beginner's guide.Beilstein journal of organic chemistry · 2025Review
- Amplified Light-Induced pThe Journal of organic chemistry · 2024Article
- Spiropyran as Building Block in Peptide Synthesis and Modulation of Photochromic Properties.Organic letters · 2024Article
- Dynamic Manipulation of Droplets on Liquid-Infused Surfaces Using Photoresponsive Surfactant.ACS central science · 2024Article
- Solvation-Tuned Photoacid as a Stable Light-Driven pH Switch for COChemistry of materials : a publication of the American Chemical Society · 2024Article
- Autonomous hydrogel locomotion regulated by light and electric fields.Science advances · 2023Article
- Spiropyran-based chromic hydrogels for COFrontiers in chemistry · 2023Article
- Spiropyran/Merocyanine Amphiphile in Various Solvents: A Joint Experimental-Theoretical Approach to Photophysical Properties and Self-Assembly.International journal of molecular sciences · 2022Article
- Spontaneous Isomerization of a Hydroxynaphthalene-Containing Spiropyran in Polar Solvents Enhanced by Hydrogen Bonding Interactions.ACS omega · 2021Article
- Molecular photoswitches in aqueous environments.Chemical Society reviews · 2021Review
- Proton-Transfer Dynamics of Photoacidic Merocyanines in Aqueous Solution.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- Spiropyran-Based Drug Delivery Systems.Frontiers in chemistry · 2021Review
- Spiropyran Meets Guanine Quadruplexes: Isomerization Mechanism and DNA Binding Modes of Quinolizidine-Substituted Spiropyran Probes.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
- Thermodynamics and kinetics of protonated merocyanine photoacids in water.Chemical science · 2020Article
- Preparation and analysis of photochromic behavior of carboxymethyl chitin derivatives containing spiropyran moieties.Designed monomers and polymers · 2020Article
Corrections and comments
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Authors and funding
5 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Six water-soluble spiropyran derivatives have been characterized with respect to the thermal and photoinduced reactions over a broad pH-interval. A comprehensive kinetic model was formulated including the spiro- and the merocyanine isomers, the respective protonated forms, and the hydrolysis products. The experimental studies on the hydrolysis reaction mechanism were supplemented by calculations using quantum mechanical (QM) models employing density functional theory. The results show that (1) the substitution pattern dramatically influences the pKa-values of the protonated forms as well as the rates of the thermal isomerization reactions, (2) water is the nucleophile in the hydrolysis reaction around neutral pH, (3) the phenolate oxygen of the merocyanine form plays a key role in the hydrolysis reaction. Hence, the nonprotonated merocyanine isomer is susceptible to hydrolysis, whereas the corresponding protonated form is stable toward hydrolytic degradation.
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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.