Red-light responsive metastable-state photoacid

Alghazwat, Osamah; Elgattar, Adnan; Khalil, Thaaer; Wang, Zhuozhi; Liao, Yi

doi:10.1016/j.dyepig.2019.107719

Cited by 11 publications

(5 citation statements)

References 34 publications

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“…This unique mPAH can be activated by red light (700 nm) in comparison to blue or green light for other mPAHs. 54 However, the quantum yield (0.007) is much lower than that of other mPAHs. Given the long lifetime of the acidic state, the achievable [H + ] of most mPAHs is mainly limited by the concentration in solution or loading in polymer.…”

Section: Coupling Mpahs With Functional Systemsmentioning

confidence: 92%

Reversible photo control of proton chemistry

Liao

2022

Phys. Chem. Chem. Phys.

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Section: Coupling Mpahs With Functional Systemsmentioning

confidence: 92%

Reversible photo control of proton chemistry

Liao

2022

Phys. Chem. Chem. Phys.

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“…[30] Reversible pH change over 2 units in aqueous conditions has been routinely achieved using MCH1. When MCH1 is used to control a functional proton acceptor, the proton acceptor must have a pK a between the pK a GS and pK a MS of MCH1, [12,16,18,19,[31][32][33] which limits the application of MCH1. Another major concern is the chemical stability in aqueous conditions.…”

Section: Introductionmentioning

confidence: 99%

Inclusion Complexes of a Metastable‐State Photoacid with High Acidity and Chemical Stability

et al. 2023

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Metastable‐state merocyanine photoacids (MCHs) have been widely applied to various chemical, material and biomedical areas to drive or control chemical processes with light. In this work, stoichiometry and association constants have been determined for inclusion complexes of a photoacid MCH1 with β‐cyclodextrin (β‐CD), 2‐hydroxypropyl‐β‐CD (HP‐β‐CD), γ‐CD and HP‐γ‐CD by means of UV‐Vis absorption titrations. The inclusion complexes were studied to enhance its acidity and chemical stability. Kinetic study showed that CDs stabilized the acidic metastable‐state and slowed its thermal relaxation. The acidity of the ground and metastable‐state (pKaGS and pKaMS) increased upon addition of CDs. The pKaMS of [MCH1·(γ‐CD)2] is as low as 0.92 in comparison with 2.25 for MCH1, which is close to the lowest pKaMS values (1.20 and 1.03) reported previously, in which case the MCH1 was structurally modified with alkylammonium side chains. Addition of CDs also significantly enhanced the chemical stability of MCH1 against hydrolysis, which is one of the major concerns for the application of MCHs. In particular, the addition of HP‐β‐CD increased the half‐life of MCH1 in aqueous solution by more than four times. Moreover, the quantum chemical calculations confirmed the stoichiometry and analyzed the binding sites and hydrogen bonds of the inclusion complexes.

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“…However, to the best of our knowledge, demonstration of prolonged light cycling stability with such molecular approaches is still limited to a maximum of 17 h of operation . Stability of photoacids is known to be affected by the solvent environment, , where higher stability can be achieved in nonaqueous solutions (e.g., methanol, ,− DMF, DMSO ,− ). In aprotic solvents, higher stability is enabled by natural suppression of the hydrolytic degradation pathway .…”

Section: Introductionmentioning

confidence: 99%

Solvation-Tuned Photoacid as a Stable Light-Driven pH Switch for CO₂ Capture and Release

de Vries,

Goloviznina,

Reiter

et al. 2023

Chem. Mater.

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Photoacids are organic molecules that release protons under illumination, providing spatiotemporal control of the pH. Such light-driven pH switches offer the ability to cyclically alter the pH of the medium and are highly attractive for a wide variety of applications, including CO 2 capture. Although photoacids such as protonated merocyanine can enable fully reversible pH cycling in water, they have a limited chemical stability against hydrolysis (<24 h). Moreover, these photoacids have low solubility, which limits the pH-switching ability in a buffered solution such as dissolved CO 2 . In this work, we introduce a simple pathway to dramatically increase stability and solubility of photoacids by tuning their solvation environment in binary solvent mixtures. We show that a preferential solvation of merocyanine by aprotic solvent molecules results in a 60% increase in pH modulation magnitude when compared to the behavior in pure water and can withstand stable cycling for >350 h. Our results suggest that a very high stability of merocyanine photoacids can be achieved in the right solvent mixtures, offering a way to bypass complex structural modifications of photoacid molecules and serving as the key milestone toward their application in a photodriven CO 2 capture process.

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Red-light responsive metastable-state photoacid

Cited by 11 publications

References 34 publications

Reversible photo control of proton chemistry

Reversible photo control of proton chemistry

Inclusion Complexes of a Metastable‐State Photoacid with High Acidity and Chemical Stability

Solvation-Tuned Photoacid as a Stable Light-Driven pH Switch for CO₂ Capture and Release

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Red-light responsive metastable-state photoacid

Cited by 11 publications

References 34 publications

Reversible photo control of proton chemistry

Reversible photo control of proton chemistry

Inclusion Complexes of a Metastable‐State Photoacid with High Acidity and Chemical Stability

Solvation-Tuned Photoacid as a Stable Light-Driven pH Switch for CO2 Capture and Release

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Solvation-Tuned Photoacid as a Stable Light-Driven pH Switch for CO₂ Capture and Release