Reversible Cross-Linking of Aliphatic Polyamides Bearing Thermo- and Photoresponsive Cinnamoyl Moieties

Tunc, Deniz; Coz, Cédric Le; Alexandre, Michaël; Desbois, Philippe; Lecomte, Philippe; Carlotti, Stéphane

doi:10.1021/ma502083p

Cited by 75 publications

(61 citation statements)

References 42 publications

(88 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Photochemical cross-linking of the polymer solutions was achieved with 364 nm light and de-cross-linking occurred with 254 nm (Figure 4c). 82 Photo-cross-linking can induce a decrease in the NP size 83 that can be exploited as for cargo release from a nanocarrier. 36 In one study, Shi et al 84 synthesized 100 nm hydrophilic PEG-grafted poly(4-cinnamic acid)- co -poly(3,4-cinnamic acid) self-assembled NPs, which were photo-cross-linked via UV irradiation with a decrease in NP size (Figure 4d).…”

Section: Miscellaneous Phototriggered Drug Release Mechanismsmentioning

confidence: 99%

See 1 more Smart Citation

Smart Nanostructures for Cargo Delivery: Uncaging and Activating by Light

et al. 2017

View full text Add to dashboard Cite

Nanotechnology has begun to play a remarkable role in various fields of science and technology. In biomedical applications, nanoparticles have opened new horizons, especially for biosensing, targeted delivery of therapeutics, and so forth. Among drug delivery systems (DDSs), smart nanocarriers that respond to specific stimuli in their environment represent a growing field. Nanoplatforms that can be activated by an external application of light can be used for a wide variety of photoactivated therapies, especially light-triggered DDSs, relying on photoisomerization, photo-cross-linking/un-cross-linking, photoreduction, and so forth. In addition, light activation has potential in photodynamic therapy, photothermal therapy, radiotherapy, protected delivery of bioactive moieties, anticancer drug delivery systems, and theranostics (i.e., real-time monitoring and tracking combined with a therapeutic action to different diseases sites and organs). Combinations of these approaches can lead to enhanced and synergistic therapies, employing light as a trigger or for activation. Nonlinear light absorption mechanisms such as two-photon absorption and photon upconversion have been employed in the design of light-responsive DDSs. The integration of a light stimulus into dual/multiresponsive nanocarriers can provide spatiotemporal controlled delivery and release of therapeutic agents, targeted and controlled nanosystems, combined delivery of two or more agents, their on-demand release under specific conditions, and so forth. Overall, light-activated nanomedicines and DDSs are expected to provide more effective therapies against serious diseases such as cancers, inflammation, infections, and cardiovascular disease with reduced side effects and will open new doors toward the treatment of patients worldwide.

show abstract

Section: Miscellaneous Phototriggered Drug Release Mechanismsmentioning

confidence: 99%

“…(c) Effect of 254 nm irradiation on gel-to-sol transition of Polyamide 6 bearing pendant cinnamoyl moieties in hexafluoroisopropanol milieu. Reprinted with permission from ref 82; copyright 2014, American Chemical Society. (d) Photo-cross-linking of cinnamate moieties under 280 nm UV irradiation leading to a size decrease in the NP.…”

Section: Figurementioning

confidence: 99%

Smart Nanostructures for Cargo Delivery: Uncaging and Activating by Light

et al. 2017

View full text Add to dashboard Cite

show abstract

“…However, inhomogeneous film morphologies caused by the inorganic nanoparticles and unreacted hydroxyl groups lead to charge trapping at the OSC/dielectric interface causing performance instabilities in these devices. Photo cross‐linked poly(vinyl cinnamate) layers have also been used,29 but the thermal reversibility of the [2 + 2] photodimerization reaction of the cinnamoyl group causes unstable film morphologies reducing reproducibility and preventing prolonged transistor operation 30. Poly(methyl methacrylate) PMMA (see Figure 1b) has also been employed as a suitable buffer layer.…”

mentioning

confidence: 99%

“…Photo cross-linked poly(vinyl cinnamate) layers have also been used, [29] but the thermal reversibility of the [2 + 2] photodimerization reaction of the cinnamoyl group causes unstable film morphologies reducing reproducibility and preventing prolonged transistor operation. [30] Poly(methyl methacrylate) PMMA (see Figure 1b) has also been employed as a suitable buffer layer. In top-gated devices, vertical phase segregation of a blend with the fluoropolymer forms a thin low-k PMMA layer at the OSC/dielectric interface, [26] while in bottom-gated devices, the OSC was generally vacuum deposited due to the PMMA layer easily dissolving in the solvents typically used to process OSCs (e.g., chlorobenzene, toluene, chloroform).…”

mentioning

confidence: 99%

Robust High‐Capacitance Polymer Gate Dielectrics for Stable Low‐Voltage Organic Field‐Effect Transistor Sensors

Rahmanudin

Tate

Marcial-Hernández

et al. 2020

Adv Elect Materials

View full text Add to dashboard Cite

Organic field‐effect transistors (OFETs) have shown great promise for use as chemical sensors for applications that range from the monitoring of food spoilage to the determination of air quality and the diagnosis of disease. However, for these devices to be truly useful, they must deliver reliable and stable low‐voltage operation over extended timescales. An important element to address this challenge is the development of a high‐capacitance gate dielectric that delivers excellent insulation with robust chemical resistance against the solution processing of organic semiconductors (OSC). The development of a bilayer gate dielectric containing a high‐k fluoropolymer relaxor ferroelectric layer modified at the OSC/dielectric interface with a photo‐crosslinked chemically resistant low‐k methacrylate‐based copolymer buffer layer is reported. Bottom‐gate OFET chemical sensors using this bilayer dielectric operate at low‐voltage with exceptional operational stability. They deliver reliable sensing performance over multiple cycles of ammonia exposure (2 to 50 ppm) with an estimated limit‐of‐detection below 1 ppm.

show abstract

“…Among different PAs, poly(ε‐caprolactam), P(ε‐CLa), commercially named nylon6 or PA6 has attained interest due to its high strength, good fatigue resistance, moderate water absorption (about 8–10%), and good resistance to most common solvents and weak acids . Besides those attractive properties, PA6 is difficult to process due to its poor solubility and to its high softening and melting temperatures caused by its high crystallinity . The ring opening polymerization (ROP) of ε‐caprolactam (ε‐CLa) constituted the most employed method to obtain PA6, P(ε‐CLa).…”

Section: Introductionmentioning

confidence: 99%

Organic-acid mediated bulk polymerization of ε-caprolactam and its copolymerization with ε-caprolactone

Sanchez‐Sanchez

Basterretxea

Mantione

et al. 2016

J. Polym. Sci. Part A: Polym. Chem.

View full text Add to dashboard Cite

Polyamides (PA) constitute one of the most important classes of polymeric materials and have gained strong position in different areas, such as textiles, fibers, and construction materials. Whereas most PA are synthesized by step‐growth polycondensation, PA 6 is synthesized by ring opening polymerization (ROP) of ε‐caprolactam (ε‐CLa). The most popular ROP methods involve the use of alkaline metal catalyst difficult to handle at large scale. In this article, we propose the use of organic acids for the ROP of ε‐CLa in bulk at 180 °C (below the polymer's melting point). Among evaluated organic acids, sulfonic acids were found to be the most effective for the polymerization of ε‐CLa , being the Brønsted acid ionic liquid: 1‐(4‐sulfobutyl)−3‐methylimidazolium hydrogen sulfate the most suitable due to its higher thermal stability. End‐group analysis by 1H nuclear magnetic resonance and model reactions provided mechanistic insights and suggested that the catalytic activity of sulfonic acids was a function of not only the acid strength, but of the nucleophilic character of conjugate base as well. Finally, the ability of sulfonic acid to promote the copolymerization of ε‐CLa and ε‐caprolactone is demonstrated. As a result, poly(ε‐caprolactam‐co‐ε‐caprolactone) copolymers with considerably randomness are obtained. This benign route allows the synthesis of poly(ester amide)s with different thermal and mechanical properties. © 2016 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2016, 54, 2394–2402

show abstract

Reversible Cross-Linking of Aliphatic Polyamides Bearing Thermo- and Photoresponsive Cinnamoyl Moieties

Cited by 75 publications

References 42 publications

Smart Nanostructures for Cargo Delivery: Uncaging and Activating by Light

Smart Nanostructures for Cargo Delivery: Uncaging and Activating by Light

Robust High‐Capacitance Polymer Gate Dielectrics for Stable Low‐Voltage Organic Field‐Effect Transistor Sensors

Organic-acid mediated bulk polymerization of ε-caprolactam and its copolymerization with ε-caprolactone

Contact Info

Product

Resources

About