Theoretical insight into azobis-(benzo-18-crown-6) ether combined with the alkaline earth metal cations

Pang, Juan; Ye, Yuanfeng; Tian, Ziqi; Pang, Xiaoying; Wu, Chunyan

doi:10.1016/j.comptc.2015.04.012

Cited by 15 publications

(10 citation statements)

References 47 publications

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“…The interactions between photoswitchable azobis-(benzo-18-crown-6) and alkaline earth metal cations were studied by DFT and reactive molecular dynamics (reactive MD) by Pang et al [ 170 ]. Optimized structures of complexes revealed that in the case of Ba 2+ complex the distance between two cations is the largest among tested complexes in their trans form, and the shortest among cis complexes.…”

Section: Crown Ethers With Azobenzene Moiety(-ies)mentioning

confidence: 99%

Azo group(s) in selected macrocyclic compounds

Wagner‐Wysiecka

Łukasik

Biernat

et al. 2018

J Incl Phenom Macrocycl Chem

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Azobenzene derivatives due to their photo- and electroactive properties are an important group of compounds finding applications in diverse fields. Due to the possibility of controlling the trans–cis isomerization, azo-bearing structures are ideal building blocks for development of e.g. nanomaterials, smart polymers, molecular containers, photoswitches, and sensors. Important role play also macrocyclic compounds well known for their interesting binding properties. In this article selected macrocyclic compounds bearing azo group(s) are comprehensively described. Here, the relationship between compounds’ structure and their properties (as e.g. ability to guest complexation, supramolecular structure formation, switching and motion) is reviewed.

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Section: Crown Ethers With Azobenzene Moiety(-ies)mentioning

confidence: 99%

Azo group(s) in selected macrocyclic compounds

Wagner‐Wysiecka

Łukasik

Biernat

et al. 2018

J Incl Phenom Macrocycl Chem

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“…Recently, on account of photo-controlled reversible supermolecular interaction between azobenzenes and cyclodextrins, hydrogels as well as films with controllable pores or passages crosslinked by the supermolecular interaction have been designed and synthesized to respond to photo-stimuli from external environment (Chen et al, 2009 ; Chiang and Chu, 2015 ; Wang et al, 2015 ). In addition to these reports, visible light driven azobenzene-based photo-switching molecules have been theoretically designed by different substitute groups (Pang et al, 2014 , 2016 ; Ye et al, 2015 ).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Photoresponsive Macromolecule for Biomedical Application

et al. 2018

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Azobenzene, a photo switcher, has attracted increasing interest due to its structural response to photo stimulus in the field of information science and chemical sensing in the recent decades. However, limited water solubility and cytotoxicity restrained their applications in the biomedical field. In research, HA-AZO has been designed as a water soluble photo switcher in biomedical application. Synthesized HA-AZO had good water-solubility and a stable π-π* transition absorbance peak trans-isomer. With exposure to UV, transformation from trans-isomer to cis-isomer of HA-AZO could be realized according to UV spectra. Reversely, trans-isomer could be gradually recovered from cis-isomer in the dark. Simultaneously, quick response and slow recovery could be detected in the process of structural change. Moreover, repeated illumination was further used to detect the antifatigue property of HA-AZO, which showed no sign of fatigue during 20 circles. The influence of pH value on UV spectrum for HA-AZO was investigated in the work. Importantly, in acid solution, HA-AZO no longer showed any photoresponsive property. Additionally, the status of HA-AZO under the effect of UV light was investigated by DLS results and TEM image. Finally, in vitro cytotoxicity evaluations were performed to show the effects of photoresponsive macromolecule on cells.

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“…Our results suggest that the polymer's PL intensity enhancement can be attributed to the coordination of the ethylene glycol ligands binding to Ba 2+ and Ru 3+ ions and to the suitable match of ion radius to cavity size, leading to the generation of a macrocycle, bearing adjacent crown ether rings and azobenzene groups, and closed azobenzene packing. Pang et al [57] employed density functional theory and reactive molecular dynamics to Figure 8a presents the DLS distribution of spherical micelles formed from the poly(NIPAM-b-Azo), with the D h being approximately 257.7 nm. After UV irradiation for 10 min, there was an obvious increase in the average diameter to 405.4 nm.…”

Section: Ion Sensing Propertiesmentioning

confidence: 99%

“…Our results suggest that the polymer's PL intensity enhancement can be attributed to the coordination of the ethylene glycol ligands binding to Ba 2+ and Ru 3+ ions and to the suitable match of ion radius to cavity size, leading to the generation of a macrocycle, bearing adjacent crown ether rings and azobenzene groups, and closed azobenzene packing. Pang et al [57] employed density functional theory and reactive molecular dynamics to demonstrate that macrocycles with azobis-(benzo-18-crown-6) and alkaline metal ions faced each other when Ba 2+ ions were complexed. They also indicated that the amide functionality that was stabilized within the cavity was provided by not only chelation of its C=O group to a metal complexed to one of the macrocycle's oligo(ethylene glycol) loops but also hydrogen bonding between the oxygen atoms of the other loops and its NH protons [58].…”

Section: Ion Sensing Propertiesmentioning

confidence: 99%

Synthesis and Self-Assembly of Multistimulus-Responsive Azobenzene-Containing Diblock Copolymer through RAFT Polymerization

et al. 2019

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This paper gathered studies on multistimulus-responsive sensing and self-assembly behavior of a novel amphiphilic diblock copolymer through a two-step reverse addition-fragmentation transfer (RAFT) polymerization technique. N-Isopropylacrylamide (NIPAM) macromolecular chain transfer agent and diblock copolymer (poly(NIPAM-b-Azo)) were discovered to have moderate thermal decomposition temperatures of 351.8 and 370.8 °C, respectively, indicating that their thermal stability was enhanced because of the azobenzene segments incorporated into the block copolymer. The diblock copolymer was determined to exhibit a lower critical solution temperature of 34.4 °C. Poly(NIPAM-b-Azo) demonstrated a higher photoisomerization rate constant (kt = 0.1295 s−1) than the Azo monomer did (kt = 0.088 s−1). When ultraviolet (UV) irradiation was applied, the intensity of fluorescence gradually increased, suggesting that UV irradiation enhanced the fluorescence of self-assembled cis-isomers of azobenzene. Morphological aggregates before and after UV irradiation are shown in scanning electron microscopy (SEM) and dynamic light scattering (DLS) analyses of the diblock copolymer. We employed photoluminescence titrations to reveal that the diblock copolymer was highly sensitive toward Ru3+ and Ba2+, as was indicated by the crown ether acting as a recognition moiety between azobenzene units. Micellar aggregates were formed in the polymer aqueous solution through dissolution; their mean diameters were approximately 205.8 and 364.6 nm at temperatures of 25.0 and 40.0 °C, respectively. Our findings contribute to research on photoresponsive and chemosensory polymer material developments.

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Theoretical insight into azobis-(benzo-18-crown-6) ether combined with the alkaline earth metal cations

Cited by 15 publications

References 47 publications

Azo group(s) in selected macrocyclic compounds

Azo group(s) in selected macrocyclic compounds

Synthesis and Characterization of Photoresponsive Macromolecule for Biomedical Application

Synthesis and Self-Assembly of Multistimulus-Responsive Azobenzene-Containing Diblock Copolymer through RAFT Polymerization

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