Understanding the torsion effects on optical properties of azobenzene derivatives

Ye, Yuanfeng; Pang, Juan; Zhou, Xiaojie; Huang, Jingwei

doi:10.1016/j.comptc.2015.11.022

Cited by 21 publications

(16 citation statements)

References 33 publications

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“…From previous research, azobenzene could not satisfy thermostability and fatigue durability, which restricted its application as a photo switch (Pang et al, 2018). Attempting to solve the problem, many efforts including our research have been applied to design new azobenzenes through all kinds of substitutions at opposite position to improve their properties as photo switches (Pang et al, 2014, 2015, 2018; Ye et al, 2016). Besides these reports, visible light driven azobenzene-based photo-switching molecules have also previously been theoretically designed by different substitute groups (Pang et al, 2014, 2015; Ye et al, 2016).…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, Investigation, and Application of a Macromolecule Photoswitch

et al. 2019

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Azobenzene (AZO) has attracted increasing interest due to its reversible structural change upon a light stimulus. However, poor fatigue durability and the photobleaching phenomenon restricts its further application. Herein, the AZO domain as a pendent group, was incorporated into copolymers, which was synthesized by radical copolymerization in the research. Structure-properties of synthesized copolymer can be adjusted by monomer ratios. Emphatically, responsive properties of copolymer in different solutions were investigated. In the DMSO solution, copolymer exhibited effective structural change, stable rapid responsive time (1 min) upon UV light at room temperature, stable relative acceptable recovery time (100 min) upon white light at room temperature, and good fatigue resistance property. In an aqueous solution, even more controllable responsive properties and fatigue resistance properties for copolymer were verified by results. More pervasively, the recovery process could be controlled by light density and temperature. In order to clarify reasons for the difference between the AZO molecule and the AZO domain of copolymer, energy barrier or interactions between single atoms or even structural units was calculated using the density functional theory (DFT). Furthermore, the status of copolymer was characterized by dynamic light scattering (DLS) and transmission electron microscope (TEM). Finally, copolymer was further functionalized with bioactive protein (concanavalin, ConA) to reduce the cytotoxicity of the AZO molecule.

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Section: Introductionmentioning

confidence: 99%

Design, Synthesis, Investigation, and Application of a Macromolecule Photoswitch

et al. 2019

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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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“…As was observed previously with the p ‐amido analogs,[11a,b] the positions of the π – π * and n – π * transitions in the UV–vis spectrum of to M‐ABDM were solvent sensitive (spectra in DMSO are shown in Figure ). This behavior is predicted to be a result of differences in solvent H‐bonding to the methoxy groups as well as to changes in the degree of twist between the aromatic rings in the trans isomer . Spectra of to M‐ABDM ( 4 ) conjugated to β‐mercaptoethanol are similar to those of to M‐ABDM ( 4 ) conjugated to the peptide and to those of to M‐ABDM ( 4 ) alone (not shown).…”

Section: Resultsmentioning

confidence: 91%

A Red‐Light Azobenzene Di‐Maleimide Photoswitch: Pros and Cons

Dong²,

Collins

et al. 2016

Advanced Optical Materials

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using BSBCA, photocontrol of peptide helicity was achieved. [ 2 ] Azobenzene dimaleimide cross-linkers (e.g., 3 (ABDM)) were described much earlier, not for the purpose of photocontrol, but as cleavable intramolecular linkages used to probe distances between thiols in proteins. [ 3 ] After the discovery of peptide conformational control by ( 1 ), di-maleimide crosslinkers were also tested as peptide and protein photocontrol elements. [ 4 ] ABDM ( 3 ) and analogs have now been used successfully to control structure and function in myosin, in restriction enzymes, in P2X receptor ion channels, and group II chaperonins. [ 5 ] The mechanism by which these azobenzene-based switches control peptide and protein conformation appears to be primarily through the end-to-end distance change that occurs upon isomerization. [ 6 ] Since the number and type of bonds connecting the two sulfur atoms in the target is the same in each case (e.g., for 1 vs 3 ), these compounds should exhibit similar end-to end-distance changes upon isomerization. The relative reactivity and selectivity of maleimides for thiols at neutral pH is reported to be higher than that of haloacetamides, [ 6c ] so that maleimide-based photoswitches would seem to be attractive reagents for complex biological targets. However, a priori, three features originally discouraged us from using the maleimide-based cross-linker ( 3 ) for peptide and protein photocontrol. The fi rst is that thiol addition to a maleimide produces Azobenzene-containing intramolecular cross-linkers with maleimide functional groups (e.g., azobenzene di-maleimide (ABDM)) have been used successfully for photocontrol of protein conformation and activity. However, the ABDM cross-linker requires short wavelength UV light (340 nm) for photoisomerization, which is highly scattered and can be absorbed by biological materials. In addition, the maleimide functional groups of ABDM are expected to lead to a mixture of stereoisomeric products upon crosslinking and these may undergo ring-opening via hydrolysis. This study reports the design and synthesis of a tetraortho -methoxy substituted ABDM crosslinker, which can be photoisomerized using red light (617 nm) and blue light (450 nm), thereby avoiding the use of UV. This new cross-linker is used to cross-link a peptide, 30ER that undergoes helix-coil transitions. As predicted, hydrolyzed succinimide cross-linked products are observed by mass spectrometry. However, although, hydrolyzed products are present, and a mixture of stereoisomers presumably forms, photoisomerization of the cross-linker nevertheless enables control of peptide helical conformation using red light. Thus, azobenzene di-maleimides are practically useful, although chemically ill-defi ned, photoswitchable cross-linkers. Scheme 1. Chemical structures of azobenzene-based thiol-reactive compounds 1 -4 .

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Understanding the torsion effects on optical properties of azobenzene derivatives

Cited by 21 publications

References 33 publications

Design, Synthesis, Investigation, and Application of a Macromolecule Photoswitch

Design, Synthesis, Investigation, and Application of a Macromolecule Photoswitch

Synthesis and Characterization of Photoresponsive Macromolecule for Biomedical Application

A Red‐Light Azobenzene Di‐Maleimide Photoswitch: Pros and Cons

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