Tuning Merocyanine Photoacid Structure to Enhance Solubility and Temporal Control: Application in Ring Opening Polymerization

Zayas, Manuel Sanchez; Dolinski, Neil D.; Self, Jeffrey L.; Abdilla, Allison; Hawker, Craig J.; Bates, Christopher M.; Alaniz, Javier Read de

doi:10.1002/cptc.201800255

Cited by 38 publications

(59 citation statements)

References 28 publications

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“…equilibrium processes for av ariety of photochromic molecules. [39,40] Additionally,t he kinetics of the reverse visible- light-driven ring opening reaction are well described by afirst-order decay. As expected, the equilibrium amount of closed form for the small molecule,D AE-BF 4 ,i ncreases as the solvent is changed from DCM (ca.…”

Section: Resultsmentioning

confidence: 99%

“…Significantly, the UV triggered isomerization reaction is well described by a first order dynamic equilibrium model [Eq. ] that has been previously used to characterize equilibrium processes for a variety of photochromic molecules . Additionally, the kinetics of the reverse visible‐light‐driven ring opening reaction are well described by a first‐order decay.

true \frac{{([], C, l, o, s, e, d, f, o, r, m)}_{t}}{{([], O, p, e, n, f, o, r, m)}_{0}} = 1 - \frac{k_{normalo normalp normale normaln} + k_{normalc normall normalo normals normale} normalE normalx normalp [- (k_{normalo normalp normale normaln} + k_{normalc normall normalo normals normale}) t]}{k_{normalo normalp normale normaln} + k_{normalc normall normalo normals normale}}

…”

Section: Resultsmentioning

confidence: 99%

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Light‐Controllable Ionic Conductivity in a Polymeric Ionic Liquid

et al. 2020

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Polymeric ionic liquids (PILs) have attracted considerable attention as electrolytes with high stability and mechanical durability. Light‐responsive materials are enabling for a variety of future technologies owing to their remote and noninvasive manipulation, spatiotemporal control, and low environmental impact. To address this potential, responsive PIL materials based on diarylethene units were designed to undergo light‐mediated conductivity changes. Key to this modulation is tuning of the cationic character of the imidazolium bridging unit upon photoswitching. Irradiation of these materials with UV light triggers a circa 70 % drop in conductivity in the solid state that can be recovered upon subsequent irradiation with visible light. This light‐responsive ionic conductivity enables spatiotemporal and reversible patterning of PIL films using light. This modulation of ionic conductivity allows for the development of light‐controlled electrical circuits and wearable photodetectors.

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Section: Resultsmentioning

confidence: 99%

true \frac{{([], C, l, o, s, e, d, f, o, r, m)}_{t}}{{([], O, p, e, n, f, o, r, m)}_{0}} = 1 - \frac{k_{normalo normalp normale normaln} + k_{normalc normall normalo normals normale} normalE normalx normalp [- (k_{normalo normalp normale normaln} + k_{normalc normall normalo normals normale}) t]}{k_{normalo normalp normale normaln} + k_{normalc normall normalo normals normale}}

…”

Section: Resultsmentioning

confidence: 99%

Light‐Controllable Ionic Conductivity in a Polymeric Ionic Liquid

et al. 2020

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true \frac{{([], C, l, o, s, e, d, f, o, r, m)}_{t}}{{([], O, p, e, n, f, o, r, m)}_{0}} = 1 - \frac{k_{normalo normalp normale normaln} + k_{normalc normall normalo normals normale} normalE normalx normalp [- (k_{normalo normalp normale normaln} + k_{normalc normall normalo normals normale}) t]}{k_{normalo normalp normale normaln} + k_{normalc normall normalo normals normale}}

…”

Section: Resultsmentioning

confidence: 99%

Light‐Controllable Ionic Conductivity in a Polymeric Ionic Liquid

et al. 2020

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“…For example, MC‐based photoacids with long disassociation lifetimes and reversible pH change (as much as 2.2 units) were recently developed by the Liao group . The Liao group and recently our group have been working on further development of several photoacids compatible in a range of different environments, from aqueous buffer solutions to organic solvents, to meet demand for applications in different areas. Azobenzene derivatives are another type of photoacids that take advantage of photochromic switching.…”

Section: Photo‐ and Ph‐addressable Architecturesmentioning

confidence: 99%

“…As the proton affinity is consistent with the stability of the photoisomers, light‐controlled acidity change can be realized by the isomerization of SP. Several SP‐based photoacids have been designed by Liao and co‐workers, Heckel and co‐workers, and our group . These have been integrated with different proton‐responsive moieties, such as acid‐catalyzed chemical reactions, hydrogen bond modulation, light‐controlled polymerization, and self‐assembly .…”

Section: Introduction To Commonly Used Photoswitches For Multiaddressmentioning

confidence: 99%

Multiaddressable Photochromic Architectures: From Molecules to Materials

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et al. 2019

Advanced Optical Materials

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the interplay between different stimuli. When multiple stimuli can be synergistically employed, there is often a significantly larger benefit as compared to the sum of analogous systems using a single stimulus. [38][39][40] Herein, we highlight recent examples of research advances using multiaddressable systems (Scheme 1). This review is broken down into six parts: i) photoand chemical-addressable architectures; ii) photo-and pHaddressable architectures; iii) photo-and thermal-addressable architectures; iv) photo-and redox-addressable architectures; v) multi-photoaddressable architectures; and vi) photo-and less common stimuli-addressable architectures. We focus on multiaddressable systems that leverage photoswitches as one of their key design features. For each section, we highlight applications in soft materials that demonstrate the potential of these multiaddressable photochromic systems. We exclude multiaddressable systems that don't contain a photoswitching molecule as they have been reviewed elsewhere. [38][39][40][41][42][43][44]

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Tuning Merocyanine Photoacid Structure to Enhance Solubility and Temporal Control: Application in Ring Opening Polymerization

Abstract: This is the author manuscript accepted for publication and has undergone full peer review but has not been through the copyediting, typesetting, pagination and proofreading process, which may lead to differences between this version and the Version of Record.

Cited by 38 publications

References 28 publications

Light‐Controllable Ionic Conductivity in a Polymeric Ionic Liquid

Light‐Controllable Ionic Conductivity in a Polymeric Ionic Liquid

Light‐Controllable Ionic Conductivity in a Polymeric Ionic Liquid

Multiaddressable Photochromic Architectures: From Molecules to Materials

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