Visible light-responsive materials: the (photo)chemistry and applications of donor–acceptor Stenhouse adducts in polymer science

Clerc, Michèle; Sandlass, Sara; Rifaie-Graham, Omar; Peterson, Julie A.; Bruns, Nico; Read de Alaniz, Javier; Boesel, Luciano F.

doi:10.1039/d3cs00508a

Cited by 21 publications

(16 citation statements)

References 174 publications

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“…[37] The DASAs transition from a non-polar triene-enol to a more polar cyclopentenone isomer in presence of light and back isomerize to the initial state in darkness. [38,39] The selection of DASA substituents on the polymer membranes associated to different encapsulated enzymes permitted wavelength selective modulation of non-equilibrium ON/OFF orthogonal enzymatic reactions in one pot. Similar transient ON/OFF permeability switching could be achieved by dissolving a merocyanine photoacid in dispersions of pH-sensitive polymer- somes that swelled in presence of blue light and reverted to the initial non-permeable state in darkness.…”

Section: Passive Transportmentioning

confidence: 99%

“…functionalized the hydrophobic leaflet of polymersome membranes composed of PEG‐ b ‐PHMA with Donor Acceptor Stenhouse Adducts (DASA) that enable solute transport only in presence of visible light (Figure 3). [37] The DASAs transition from a non‐polar triene‐enol to a more polar cyclopentenone isomer in presence of light and back isomerize to the initial state in darkness [38,39] . The selection of DASA substituents on the polymer membranes associated to different encapsulated enzymes permitted wavelength selective modulation of non‐equilibrium ON/OFF orthogonal enzymatic reactions in one pot.…”

Section: Membrane Transportmentioning

confidence: 99%

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Emergence of Cell Behavior Through Feedback Control of Polymersome Membrane Transport

Rifaie‐Graham

2023

ChemSystemsChem

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Artificial cell and organelle construction has recently gained substantial attention to generate simplified models for understanding of biological phenomena, or micro‐ and nanomachines for biomedical and biotechnological applications. A wide array of building blocks has been employed to build these systems as membraneless structures with the ability to compartmentalize chemical reactions by enhanced partitioning, or as membrane‐defined entities that provide a physical barrier that inhibits the interference of external factors. While these systems present unique properties that enable high fidelity to biological processes, they present limited ability to recreate the high selectivity and specificity of small molecule trafficking observed in biological membranes. Owing to their high chemical versatility, polymers can be leveraged to generate 3D structures that resemble biological membranes while providing transmembrane chemical motifs that enable responsiveness to a wide array of stimuli. This Concept Article discusses the ability to control membrane transport facilitating the emergence of out‐of‐equilibrium feedback mechanisms that ultimately modulate enzymatic rates. This can be employed to engineer future artificial cells and organelles that display homeostasis as a mechanism of self‐adaptation to continuously evolving environments.

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Section: Passive Transportmentioning

confidence: 99%

Section: Membrane Transportmentioning

confidence: 99%

Emergence of Cell Behavior Through Feedback Control of Polymersome Membrane Transport

Rifaie‐Graham

2023

ChemSystemsChem

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“…But different compounds showed different mechanisms, including photo–dependent fatigue mechanism and interactions with additives [ 71 ]. Due to the unique properties of DASAs described above, these compounds have potential applications in chemical and thermal sensors [ 72 ], drug delivery [ 73 , 74 ], liquid crystals, rewritable paper [ 68 ], polymer science [ 75 ], and so on.…”

Section: Negatively Photochromic Compoundsmentioning

confidence: 99%

From Visible to Near–Infrared Light–Triggered Photochromism: Negative Photochromism

Li,

Mou,

Yamada

et al. 2023

Molecules

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Photochromic compounds, whose key molecular properties can be effectively modulated by light irradiation, have attracted significant attention for their potential applications in various research fields. The restriction of photoisomerization coloration induced by ultraviolet light limits their applications in the biomedical field and some other fields. Negative photochromism, wherein a relatively stable colored isomer transforms to a colorless metastable isomer under low–energy light irradiation, offers advantages in applications within materials science and life science. This review provides a summary of negatively photochromic compounds based on different molecular skeletons. Their corresponding design strategies and photochromic properties are presented to provide practical guidelines for future investigations. Negatively photochromic compounds can effectively expand the range of photochromic switches for future applications, offering unique properties such as responsiveness to visible to near–infrared light.

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“…A critical assessment of prevailing controversies and counterarguments provides a brief view of various aspects of FA polymerization chemistry . Moreover, FA stands out, and its complex mechanism and polymerization kinetics as primary alcohol have attracted the interest of chemical scientists and continue to be the subject of discussion . In addition, biomass-derived furans such as FA may have greater potential, as the search for sustainable chemical and environmental remediation continues .…”

Section: Introductionmentioning

confidence: 99%

“…16 Moreover, FA stands out, and its complex mechanism and polymerization kinetics as primary alcohol have attracted the interest of chemical scientists and continue to be the subject of discussion. 22 In addition, biomass-derived furans such as FA may have greater potential, as the search for sustainable chemical and environmental remediation continues. 23 Furthermore, studies on the tunable performance of FA polymers involving chemical reactivity, mechanical strength, and thermal stability may open new routes for designing useful materials.…”

Section: Introductionmentioning

confidence: 99%

Boron Nitride-Based Polyester Nanocomposite Films with Enhanced Barrier and Mechanical Performances

Miah,

Ding,

Zhao

et al. 2024

ACS Appl. Polym. Mater.

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Developing sustainable plastics, for instance, green poly(ethylene 2,5furandicarboxylate) (PEF), is a promising pathway to decrease the reliance on petroleumbased plastics and the pollution of the environment. However, the preparation of highperformance PEF materials that integrate superior barrier and mechanical properties remains a huge challenge. In this study, a BNNSs/PEF composite film with excellent mechanical and barrier performance was fabricated by using furfuryl alcohol simultaneously acting as a high-level dispersant and interfacial reinforcement matrix for BNNSs. The optimized BNNS/PEF composite film with 0.2 wt % BNNSs (BP2) shows a compacted aligned structure and excellent comprehensive performance with 79.2 MPa tensile strength (43% enhancement), 4.2 GPa Young's modulus (83% enhancement), high gas barrier, and enhanced thermal stability. Remarkably, fruit testing conditions (e.g., relative humidity of 90−95%, temperature of 30, and natural light) showed that the BP2 composite film extended the shelf life of fresh strawberries by at least at least 5 days in an ambient environment. The overall performance of the BP2 composite film is optimized to be superior, which opens up an avenue for practical applications in the field of packaging materials.

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Visible light-responsive materials: the (photo)chemistry and applications of donor–acceptor Stenhouse adducts in polymer science

Abstract: In this review, the recent developments and challenges in the field of donor–acceptor Stenhouse adduct (DASA)-containing polymers are discussed, aiming at providing a better understanding of the interplay between the properties of both matrix and photoswitch.

Cited by 21 publications

References 174 publications

Emergence of Cell Behavior Through Feedback Control of Polymersome Membrane Transport

Emergence of Cell Behavior Through Feedback Control of Polymersome Membrane Transport

From Visible to Near–Infrared Light–Triggered Photochromism: Negative Photochromism

Boron Nitride-Based Polyester Nanocomposite Films with Enhanced Barrier and Mechanical Performances

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