Synthesis and Characterization of N,N-Bis(2-hydroxyethyl) Cinnamamide as a Photo-Responsive Monomer

Jin, Chunli; Sun, Xiaojie; Wu, Linbo

doi:10.1163/138577210x541196

Cited by 15 publications

(15 citation statements)

References 18 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The chain‐extension reaction leading to PURs was carried out by reactive extrusion. For photo‐responsive SME, N,N ‐bis(2‐hydroxyethyl) cinnamide (BHECA) was selected due to the presence of a pendant cinnamide moiety undergoing photoreversible [2+2] cycloaddition reactions in function of a certain wavelength (λ switch = 254 nm) . PCL served as a semicrystalline segment ensuring the permanent domains.…”

Section: Introductionmentioning

confidence: 99%

Poly(ε‐caprolactone) and Poly(ω‐pentadecalactone)‐Based Networks with Two‐Way Shape‐Memory Effect through [2+2] Cycloaddition Reactions

Pilate

Stoclet

Mincheva

et al. 2017

Macro Chemistry & Physics

View full text Add to dashboard Cite

In this work, the synthesis and characterization of triple-shape and twoway shape-memory effect of novel poly(ester-urethane)s (PURs) made of a poly(ε-caprolactone) (PCL) and poly(ω-pentadecalactone) (PPDL) segments and N,N-bis(2-hydroxyethyl)cinnamide (BHECA) monomer by reactive extrusion (REx) is reported. PCL and PPDL are chosen as semicrystalline segments because of their inherent ability to undergo tensile elongation upon cooling, as prerequisite for the two-way shape-memory effect. BHECA is used as the "cross-linker" due to its ability to participate in reversible [2+2] cycloaddition reaction and to mainly maintain the crystalline features of semicrystalline precursors within these PURs. This novel simple strategy is considered extremely versatile and adaptive because of the possibility to vary crystallizable segments and coupling agents, thus paving the way to the design of a multitude of triple (or more) shape-memory polymers with two-way behavior. Feasibility with PURs containing PCL, PPDL, and BHECA is demonstrated by adjusting the shape-memory behavior (one and two-way effects), and studying the structure-property relationships of the resulting PURs by DSC, DMTA, and 2D wide angle X-ray scattering analyses while varying the weight composition of the two semicrystalline segments.

show abstract

Section: Introductionmentioning

confidence: 99%

Poly(ε‐caprolactone) and Poly(ω‐pentadecalactone)‐Based Networks with Two‐Way Shape‐Memory Effect through [2+2] Cycloaddition Reactions

Pilate

Stoclet

Mincheva

et al. 2017

Macro Chemistry & Physics

View full text Add to dashboard Cite

show abstract

“…Some of the most prominent focus on the development of polymer devices with visible and near-IR imaging modalities for soft tissue optical visualization, Diels–Alder dynamic cross-linked polyurethane (PUR) structures containing polydopamine particles with conferred self-healing properties, polymer systems containing photothermal fillers for improved spatiotemporal shape control under the exposure of different light illumination sequences, as well as polymer composites loaded with carbon nanotubes or graphene nanoplatelets for good electrical and self-driven ability. Different SMPs were described using small photoreactive molecular reversible switches such as cinnamic acid and its analogues (cinnamylidene acetic acid or N , N -bis-2-(hydroxyethyl)cinnamide or nitro-cinnamate) in PUR multiblocks − and azobenzene . However, the most frequent difficulties, affecting the performances and the reproducibility in these systems, are related to the multistep synthetic approaches for active agent incorporation along the polymer backbone, the precise working wavelengths, the spatioselective geometrical position of the molecule fragments to form the cycloadditive dimers, and the required soft material properties ensuring the chain mobility.…”

Section: Introductionmentioning

confidence: 99%

Fast IR-Actuated Shape-Memory Polymers Using in Situ Silver Nanoparticle-Grafted Cellulose Nanocrystals

Toncheva

Khelifa

Paint

et al. 2018

ACS Appl. Mater. Interfaces

View full text Add to dashboard Cite

In recent years, shape-memory polymers (SMPs) have gained a key position in the realm of actuating applications from daily life products to biomedical and aeronautic devices. Most of these SMPs rely mainly on shape changes upon direct heat exposure or after stimulus conversion (e.g., magnetic field and light) to heat, but this concept remains significantly limited when both remote control and fine actuation are demanded. In the present study, we propose to design plasmonic silver nanoparticles (AgNPs) grafted onto cellulose nanocrystals (CNCs) as an efficient plasmonic system for fast and remote actuation. Such CNC- g-AgNPs "nanorod-like" structures thereby allowed for a long-distance and strong coupling plasmonic effect between the AgNPs along the CNC axis, thus ensuring a fast photothermal shape-recovery effect upon IR light illumination. To demonstrate the fast and remote actuation promoted by these structures, we incorporated them at low loading (1 wt %) into poly(ε-caprolactone) (PCL)-based networks with shape-memory properties. These polymer matrix networks were practically designed from biocompatible PCL oligomers end-functionalized with maleimide and furan moieties in the melt on the basis of thermoreversible Diels-Alder reactions. The as-produced materials could find application in the realm of soft robotics for remote object transportation or as smart biomaterials such as self-tightening knots with antibacterial properties related to the presence of the AgNPs.

show abstract

“…LaSMP realizes the shape memory function through reversible photochemical reactions structures (Lendlein et al, 2005;Snyder and Tong, 2005). The photochemical reactions occur with the stimulus of ultraviolet lights and do not generate heat (Jin et al, 2011). With the dynamic stiffness feature, flexible LaSMP provides a non-contact alternative for the experimental data and constitutive model of LaSMP (Beblo, 2010;Sodhi and Rao, 2010a), it is promising to establish a generic LaSMP (both forward and reverse reactions) model and to analyze the dynamic response of LaSMP-laminated structures.…”

Section: Introductionmentioning

confidence: 99%

Responses of rings with light-activated shape memory polymers regulated by neural network and phase shift

Dong

Tzou

2017

Journal of Intelligent Material Systems and Structures

View full text Add to dashboard Cite

Light-activated shape memory polymer is able to hold the temporary shape and to change the permanent shape upon exposures of ultraviolet lights with specific wavelengths. The study aims to provide a non-contact and temperature-independent technique to suppress the vibration of rings using light-activated shape memory polymer. Forced responses of flexible rings laminated with light-activated shape memory polymer patches are evaluated. Dynamic equations of light-activated shape memory polymer–laminated rings are established first. With the modal expansion method, the modal force of light-activated shape memory polymer actuators is derived and then the modal responses (with or without control) are evaluated. A generic kth order and its simplified light-activated shape memory polymer constitutive equations are established based on the chemical kinetics. Light-activated shape memory polymer shows the dynamic stiffness when exposed to ultraviolet lights, and this feature is reflected in its constitutive equations influenced by light intensity, material constant, thickness, and so on. With these derivations, the relationship of light intensity and modal force is established and it exhibits a hysteresis phenomenon. The procedure of identifying the hysteresis model using the neural network is described. Then, the phase shift and neural network control techniques are, respectively, applied to enhance the control effects. The neural network vibration control (with a maximal reduction in 98.1%) is very effective to improve light-activated shape memory polymer’s actuation capability.

show abstract

Synthesis and Characterization of N,N-Bis(2-hydroxyethyl) Cinnamamide as a Photo-Responsive Monomer

Cited by 15 publications

References 18 publications

Poly(ε‐caprolactone) and Poly(ω‐pentadecalactone)‐Based Networks with Two‐Way Shape‐Memory Effect through [2+2] Cycloaddition Reactions

Poly(ε‐caprolactone) and Poly(ω‐pentadecalactone)‐Based Networks with Two‐Way Shape‐Memory Effect through [2+2] Cycloaddition Reactions

Fast IR-Actuated Shape-Memory Polymers Using in Situ Silver Nanoparticle-Grafted Cellulose Nanocrystals

Responses of rings with light-activated shape memory polymers regulated by neural network and phase shift

Contact Info

Product

Resources

About