Azopolymers with imide structures as light-switchable membranes in controlled gas separation

Bujak, Karolina; Nocoń, Klaudia; Jankowski, Andrzej; Wolińska‐Grabczyk, Aleksandra; Schab‐Balcerzak, Ewa; Janeczek, Henryk; Konieczkowska, Jolanta

doi:10.1016/j.eurpolymj.2019.05.051

Cited by 17 publications

(17 citation statements)

References 49 publications

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“…1 H NMR (400 MHz, DMSO- d 6 ) δ = 10.61 (br, 1H), 7.90–7.84 (m, 4H), 2.14 (s, 3H). The NMR spectrum is in good agreement to that reported in the literature …”

Section: Methodssupporting

confidence: 90%

Photoswitchable Antagonists for a Precise Spatiotemporal Control of β₂-Adrenoceptors

et al. 2020

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β2-Adrenoceptors (β2-AR) are prototypical G-protein-coupled receptors and important pharmacological targets with relevant roles in physiological processes and diseases. Herein, we introduce Photoazolol-1–3, a series of photoswitchable azobenzene β2-AR antagonists that can be reversibly controlled with light. These new photochromic ligands are designed following the azologization strategy, with a p-acetamido azobenzene substituting the hydrophobic moiety present in many β2-AR antagonists. Using a fluorescence resonance energy transfer (FRET) biosensor-based assay, a variety of photopharmacological properties are identified. Two of the light-regulated molecules show potent β2-AR antagonism and enable a reversible and dynamic control of cellular receptor activity with light. Their photopharmacological properties are opposite, with Photoazolol-1 being more active in the dark and Photoazolol-2 demonstrating higher antagonism upon illumination. In addition, we provide a molecular rationale for the interaction of the different photoisomers with the receptor. Overall, we present innovative tools and a proof of concept for the precise control of β2-AR by means of light.

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“…1 H NMR (400 MHz, DMSO- d 6 ) δ = 10.61 (br, 1H), 7.90–7.84 (m, 4H), 2.14 (s, 3H). The NMR spectrum is in good agreement to that reported in the literature …”

Section: Methodssupporting

confidence: 90%

Photoswitchable Antagonists for a Precise Spatiotemporal Control of β₂-Adrenoceptors

et al. 2020

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“…Scientific research on the modification and functionalization of PIs in order to endow them with smart functions is of particular challenge nowadays, one perspective route being the incorporation of ABn structural unit in their macromolecular chains. In this context, several synthetic routes have been developed so far, most of them involving the general condensation reaction of ABn-functionalized monomers ,− or the postfunctionalization strategy which allows ABn chromophores to be introduced into reactive precursor polymers. − The first method is the most used because of the better control of sequence chromophore distribution.…”

Section: Introductionmentioning

confidence: 99%

Structural Chemistry-Assisted Strategy toward Fast Cis–Trans Photo/Thermal Isomerization Switch of Novel Azo-Naphthalene-Based Polyimides

Constantin¹,

Sava²,

Damaceanu³

2021

Macromolecules

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Pursuing the research toward smart material development, novel azopolyimides containing highly photoresponsive azo-naphthalene moieties are synthesized and fully characterized toward efficient, fast, and stable cis−trans photo/ thermal isomerization switch. To this aim, a novel triphenylmethane diamine carrying a photochromic receptor is prepared and used in polycondensation with aromatic dianhydrides. Insights into molecular weights and thermal, optical, and electrochemical characteristics are employed to accomplish basic characterizations. To prove the switching characteristics insufficiently explored for polyimides (PIs), trans−cis and cis−trans photo/thermal isomerizations are surveyed by UV−vis and 1 H NMR investigations. UV− vis absorption studies reveal unprecedented fast trans−cis switches (47−130 s) through rotation mechanism in dimethylformamide, with one of the highest efficiencies reported nowadays for PIs, up to 90.2%. Slower thermal cis−trans relaxation is experienced owing to a nonpolarity-assisted inversion mechanism. After 15 repetitive trans−cis−trans switching cycles, an excellent stability up to 96.29% is recorded. The PI films obtained without any dilution in solid state reach the photostationary state after longer irradiation time but with excellent efficiency, up to 75.7%, and trans−cis−trans conversion stability, up to 92.68%, after 10 cycles. The photoisomerization studies are completed by 1 H NMR that evidences spectral profiles change during irradiation. Perspective optoelectronic applications that demand photocontrollable functions are foreseen.

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“…According to previous reports, the trans / cis isomerization of azobenzene is able to generate apparent geometrical and dipole changes [ 52 , 53 , 54 , 55 ]. CO 2 sorption tests were carried out to obtain the uptake capacity, which can be used to investigate the dynamic photoswitching for controllable CO 2 adsorption of JJU-1.…”

Section: Resultsmentioning

confidence: 92%

Rational Construction of a Responsive Azo-Functionalized Porous Organic Framework for CO2 Sorption

Yuan

Sun

2021

Molecules

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An azo-functionalized porous organic framework (denoted as JJU-1) was synthesized via FeCl3-promoted oxidative coupling polymerization. By virtue of a porous skeleton and a light/heat responsive azo functional group, this task-specific JJU-1 displays a reversible stimuli-responsive adsorption property triggered by UV irradiation and heat treatment. The initial Brunauer–Emmet–Teller (BET) surface area of this porous material is 467 m2 g–1. The CO2 sorption isotherms exhibit a slight decrease after UV irradiation because of the trans to cis conversion of the azo functional skeleton. It is worth mentioning that the responsive CO2 adsorption performance can be recycled for three cycles via alternating external stimuli, confirming the excellently reversible switchability of trans-to-cis isomerization and controllable CO2 adsorption.

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Azopolymers with imide structures as light-switchable membranes in controlled gas separation

Cited by 17 publications

References 49 publications

Photoswitchable Antagonists for a Precise Spatiotemporal Control of β₂-Adrenoceptors

Photoswitchable Antagonists for a Precise Spatiotemporal Control of β₂-Adrenoceptors

Structural Chemistry-Assisted Strategy toward Fast Cis–Trans Photo/Thermal Isomerization Switch of Novel Azo-Naphthalene-Based Polyimides

Rational Construction of a Responsive Azo-Functionalized Porous Organic Framework for CO2 Sorption

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Azopolymers with imide structures as light-switchable membranes in controlled gas separation

Cited by 17 publications

References 49 publications

Photoswitchable Antagonists for a Precise Spatiotemporal Control of β2-Adrenoceptors

Photoswitchable Antagonists for a Precise Spatiotemporal Control of β2-Adrenoceptors

Structural Chemistry-Assisted Strategy toward Fast Cis–Trans Photo/Thermal Isomerization Switch of Novel Azo-Naphthalene-Based Polyimides

Rational Construction of a Responsive Azo-Functionalized Porous Organic Framework for CO2 Sorption

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Product

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Photoswitchable Antagonists for a Precise Spatiotemporal Control of β₂-Adrenoceptors

Photoswitchable Antagonists for a Precise Spatiotemporal Control of β₂-Adrenoceptors