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azobenzene‑Based Solar Thermal Fuels:A Review

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Nano-Micro Letters 2022年第8期14卷 232-268页

作者： Bo Zhang Yiyu Feng Wei Feng School of Materials Science and Engineering Tianjin UniversityTianjin 300350People’s Republic of China Tianjin Key Laboratory of Composite and Functional Materials Tianjin 300350People’s Republic of China Key Laboratory of Materials Processing and Mold Ministry of EducationZhengzhou UniversityZhengzhou 450002People’s Republic of China

The energy storage mechanism of azobenzene is based on the transformation of molecular cis and trans isomerization,while NBD/QC,DHA/VHF,and fulvalene dimetal complexes realize the energy storage function by changing the molecular structure.Acting as“molecular batteries,”they can exhibit excellent charging and discharging behavior by converting between trans and cis isomers or changing molecular structure upon absorption of ultraviolet light.Key properties determining the performance of STFs are stored energy,energy density,half-life,and solar energy conversion efficiency.This review is aiming to provide a comprehensive and authoritative overview on the recent advancements of azobenzene molecular photoswitch system in STFs fields,including derivatives and carbon nano-templates,which is emphasized for its attractive performance.Although the energy storage performance of Azo-STFs has already reached the level of commercial lithium batteries,the cycling capability and controllable release of energy still need to be further explored.For this,some potential solutions to the cycle performance are proposed,and the methods of azobenzene controllable energy release are summarized.Moreover,energy stored by STFs can be released in the form of mechanical energy,which in turn can also promote the release of thermal energy from STFs,implying that there could be a relationship between mechanical and thermal energy in Azo-STFs,providing a potential direction for further research on Azo-STFs.

关键词： azobenzene Solar thermal fuels Nanocarbon template Controllable energy release Phase change materials

Fabrication of azobenzene-functionalized porous polymers for selective CO_(2) capture

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Chinese Journal of Chemical Engineering 2022年第3期35卷 24-30页

作者： Ding-Ming Xue Wen-Juan Zhang Xiao-Qin Liu Shi-Chao Qi Lin-Bing Sun State Key Laboratory of Materials-Oriented Chemical Engineering Jiangsu National Synergetic Innovation Center for Advanced Materials(SICAM)College of Chemical EngineeringNanjing Tech UniversityNanjing 211816China

Many solid adsorbents have been prepared for the CO_(2)capture.In particular,the photoresponsive adsorbents have attracted extensive interests because of their tunable pore structure and variable responsive behaviors provoked by the external light.However,it is challenging to fabricate the photoresponsive adsorbents featured the big CO_(2)capacity and high CO_(2)selectivity.Herein,copolymerized between 4-phenylazobenzoyl chloride,2,4,6-trichloro-1,3,5-triazine and melamine,a series of azobenzenefunctionalized porous polymers(PTM-AZOs)are successfully synthesized.The PTM-AZOs are verified in possession of proper pore structures,large surface area and photoconductive properties through a series of characterization.The PTM-AZO-2 with the trans-isomerization exhibits the best CO_(2)adsorption amount of 2.7 mmol·g^(-1)(273 K and 0.1 MPa),while the CO_(2)/N_(2)selectivity can reach 2459 and 607 on the trans-and cis-isomerization,respectively.The regulatable pore structures controlled by the photoresponsive azobenzene groups affect the CO_(2)capture performance of the PTM-AZOs.

关键词： Adsorption CO_(2)capture Selectivity azobenzene Photoresponse

The Shackling Effect in Cyclic azobenzene Liquid Crystal

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Chinese Journal of Polymer Science 2022年第6期40卷 584-592页

作者： Yang Xiao Chong He Zi-Fan Yang Er-Qiang Chen Huan-Jun Lu Xiao-Hong Li Ying-Feng Tu State and Local Joint Engineering Laboratory for Novel Functional Polymeric Materials College of ChemistryChemical Engineering and Materials ScienceSoochow UniversitySuzhou 215123China Beijing National Laboratory for Molecular Sciences Key Laboratory of Polymer Chemistry and Physics of Ministry of EducationCenter for Soft Matter Science and EngineeringCollege of ChemistryPeking UniversityBeijing 100871China Jiangsu Key Laboratory of Micro and Nano Heat Fluid Flow Technology and Energy Application School of Physical Science and TechnologySuzhou University of Science and TechnologySuzhou 215009China

We demonstrate here a novel method for the design of liquid crystals(LCs)via the cyclization of mesogens by flexible chains.For two azobenzene-4,4′-dicarboxylate derivatives,the cyclic dimer,cyclic bis(tetraethylene glycol azobenzene-4,4′-dicarboxylate)(CBTAD),shows LC properties with smectic A phase,while its linear counterpart,bis(2-(2′-hydroxyethyloxy))ethyl azobenzene-4,4′-dicarboxylate(BHAD),has no LC phase.The difference is ascribed to the shackling effect from the cyclic topology,which leads to the much smaller entropy change during phase transitions and increases the isotropic temperature greatly for cyclics.In addition,the trans-to-cis isomerization of azobenzene groups under UVlight is also limited in CBTAD.With the reversible isomerization of azobenzene groups,CBTAD showed interesting isothermal phase transition behaviors,where the LC phase disappeared upon photoirradiation of 365 nm UV-light,and recovered when the UV-light was off.Combined with the smectic LC nature,a novel UV-light tuned visible light regulator was designed,by simply placing CBTAD in two glass plates.The scattered phase of smectic LC was utilized as the“OFF”state for light passage,while the UV-light induced isotropic phase was utilized as the“ON”state.The shackling effect outlined here should be applicable for the design of cyclic LC oligomers/polymers with special properties.

关键词： azobenzene Cyclic Liquid crystals Isothermal phase transition

Chiroptical Generation,Switching,and Long-Term Memory in Supramolecular azobenzene-Pendant Polymer: Regulation by Cellulose Peralkyl Esters,D-/L-Glucose Permethyl Esters,Solvents,UV Light Irradiation,and Thermal Annealing Process

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Chinese Journal of Chemistry 2023年第24期41卷 3625-3632页

作者： Shiyuan Yi Laibing Wang Xiaoxiao Cheng Michiya Fujiki Wei Zhang State and Local Joint Engineering Laboratory for Novel Functional Polymeric Materials Jiangsu Engineering Laboratory of Novel Functional Polymeric MaterialsSuzhou Key Laboratory of Macromolecular Design and Precision SynthesisCollege of Chemistry Chemical Engineering and Materials ScienceSoochow UniversitySuzhouJiangsu215123 China Graduate School of Science and Technology Nara Institute of Science and Technology8916-5 TakayamaIkomaNara630-0192 Japan School of Chemical and Environmental Engineering Anhui Polytechnic UniversityWuhuAnhui241000 China

Various optically active polymers are known to afford sophisticated chirality-related functionalities,i.e.,asymmetric catalysis,chiroptical switching and memory in UV-vis-NIR region,chromatographic separation of enantiomers,and sensors for molecular chirality.Recently,material researchers have paid much attention to the design of chiral supramolecular architectures from achiral polymers upon intermolecular interactions with help of greener biosources.The present article reports an instantaneous generation of ambidextrous supramolecules revealing light-driven chiroptical switching/memory in UV-vis region when achiral azobenzene-containing vinylpolymers are non-covalently interacted with alkyl ester derivatives of natural cellulose and D-/L-glucose.It was recognized that the semi-synthetic biomaterials efficiently work as chirality-inducing scaffoldings to several achiral and optically inactive molecules,oligomers,and polymers.Our successful results shed light on a new approach of how inexpensive poly-/mono-saccharide derivatives can afford supramolecular chiroptical systems with the azobenzene pendant polymer as aggregates in suspension and liquid-crystalline films with minimal energy,time,and cost.

关键词： Aggregation azobenzene Nanostructures Functional polymers Supramolecular chirality

Facile synthesis of azobenzene-embedded conjugated macrocycles for optically switchable single-crystal transistors and tunable supramolecular assemblies

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Aggregate

Aggregate 2023年第6期4卷 101-109页

作者： Dongdong Chang Xuetao Xiao Dongyue An Rong Zhang Xianyu Song Yunqi Liu Yan Zhao Xuefeng Lu Department of Materials Science State Key Laboratory of Molecular Engineering of PolymersFudan UniversityShanghaiChina Key Laboratory of Water Environment Evolution and Pollution Control in Three Gorges Reservoir School of Environmental and Chemical EngineeringChongqing Three Gorges UniversityChongqingChina

A series of newπ-conjugated macrocycles(AzoM-n-E,n 1–3)incorporating=azobenzene units have been synthesized by a facile strategy in one-pot reaction.The resultant azobenzene-embedded macrocycles feature intrinsic photoresponsive behaviors and intriguing supramolecular assembling properties.The smallest macro-cycle AzoM-1-E with a rigid planar conjugated backbone structure is used to prepare the single crystal transistors,showing reversible optical tunability.The moderate size macrocycle AzoM-2-E assembles into a dimer in the form of interpenetration throughπ-πstacking between azobenzene units.The largest macrocycle AzoM-3-E with enhancedﬂexibility can adaptively assemble with various types of electron-deﬁcient guests accompanied by distortion of azobenzene.Typically,AzoM-3-E assembles with the planar F4-TCNQ to form a tetragonal geometry by C-F⋅⋅⋅π and π-π interactions,while the assembly with ellipsoidal C70 viaπ-πinteractions induces AzoM-3-E to form a boat-shaped geometry.This work will shed new light on the development of functional conjugated macrocycles in organic electronics.

关键词： azobenzene conjugated macrocycle host-guest interaction photoresponsive transistors supramolecular assembly

Light-driven interconversion of Pd_(2)L_(4)cage and mononuclear PdL_(2)mediated by the isomerization of azobenzene ligand

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Chinese Chemical Letters 2023年第6期34卷 358-361页

作者： Jinkang Zhu Xujin Chen Xin Jin Qiaochun Wang Key Laboratory for Advanced Materials Joint International Research Laboratory of Precision Chemistry and Molecular EngineeringFeringa Nobel Prize Scientist Joint Research CenterFrontiers Science Center for Materiobiology and Dynamic ChemistryInstitute of Fine ChemicalsSchool of Chemistry and Molecular EngineeringEast China University of Science and TechnologyShanghai 200237China

The lantern-shaped cage Pd_(2)L_(4)and tweezer-like PdL_(2)can be synthesized from the trans-and cis-isomer of an azobenzene-containing ligand,respectively,which were characterized by^(1)H,^(13)C,^(1)H-^(1)H COSY,DOSY NMR spectroscopies,high-resolution ESI-MS and density function theory(DFT)calculations.The interconversion of Pd_(2)L_(4)and PdL_(2)can be achieved via the cis-trans isomerization of the azobenzene unit on the ligand upon alternative irradiation of light 365 nm or 420 nm.

关键词： Molecular cage azobenzene Isomerization Pd_(2)L_(4) PdL_(2)

azobenzene Based Photo-responsive Mechanical Actuator Fabricated by Intermolecular H-bond Interaction

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Chinese Journal of Polymer Science 2021年第4期39卷 417-424,I0005页

作者： Chun-Yan Yu Jia-Hui Mu Yun-Lei Fu Yun-Chao Zhang Ji-Shu Han Rui-Yang Zhao Jia Zhao Zi-Hao Wang Zhong-Cheng Zhao Wei-Jun Li Fu-Sheng Liu State Key Laboratory Base of Eco-chemical Engineering College of Chemical EngineeringQingdao University of Science and TechnologyQingdao 266042China Taishan Scholar Advantage and Characteristic Discipline Team of Eco Chemical Process and Technology College of Chemistry and Molecular EngineeringQingdao University of Science and TechnologyQingdao 266042China State Key Laboratory Breeding Base of Green Chemistry Synthesis Technology College of Chemical EngineeringZhejiang University of TechnologyHangzhou 310014China

Photo-responsive mechanical actuator is a class of stimuli-responsive materials transferring light to mechanical energy through macroscopic transformation.To fabricate photo-responsive mechanical actuator,soft polymeric materials crosslinked with functional bridging structures are desired.Supramolecular interaction is a relatively common way to fabricate crosslinked materials due to its excellent self-assembly performance.And azobenzene and derivatives are ideal candidates of photo-responsive materials because of the unique photo-induced trans-cis isomerization.Here,a new kind of crosslinked materials based on supramolecular interaction between 4,4'-dihydroxyazobenzene and chitosan is reported.Under 355 nm irradiation,the macroscopic bending of polymeric materials occurs rapidly due to the photo-isomerization of 4,4-dihydroxyazobenzene.Meanwhile,the photo-responsive mechanical actuator can also lift weight which is up to 200 times that of the actuator itself,and convert energy from light to mechanical work efficiently.This report suggests a new kind of photo-responsive actuator based on supramolecular interaction and may be helpful to contribute a theoretical basis to the design and synthesis of photo-responsive mechanical actuator suitable for large-scale manufacturing industrialization in future.

关键词： Photo-response Supramolecular interaction Mechanical actuator azobenzene Energy conversion

azobenzene quaternary ammonium salt for photo-controlled and reusable disinfection without drug resistance

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Chinese Chemical Letters 2023年第2期34卷 440-445页

作者： Yuhong Zhu Pengfei Li Caikun Liu Mengqi Jia Yadong Luo Dengfeng He Chunyan Liao Shiyong Zhang College of Chemistry Sichuan UniversityChengdu 610064China College of Biomedical Engineering and National Engineering Research Center for Biomaterials Sichuan UniversityChengdu 610064China

The abuse of antibiotics causes severe bacterial resistance, and the shortage of antibiotics has created a global public health crisis. This situation has prompted people to develop new antibacterial agents independent of traditional antibiotics. Here, we created a series of photosensitive azobenzene-quaternary ammonium salt smart antibacterial agents by connecting azobenzene with amines with different chain lengths to improve the antibacterial selectivity of quaternary ammonium salt(QAS) and prevent the accumulation of active QAS in the environment. After trans-cis isomerization, the solubility of the title compound(compound 4) increased and the antibacterial property enhanced. The experimental results suggested that the antibacterial effect of compound 4 was significantly enhanced after 365 nm light irradiation, and it had photosensitive intelligent antibacterial activity and could be reused. Notably, we did not obtain any mutants of Staphylococcus aureus or Escherichia coli resistant to compound 4. In general,compound 4 has the advantages of high yield, photo-controllable antibacterial properties, reusability, and does not induce bacterial resistance. This photosensitive antibacterial compound provides a new idea for the construction of intelligent disinfectants and is expected to be a candidate for disinfectants in public facilities and medical architecture.

关键词： azobenzene Quaternary ammonium salt Photosensitivity Repeatability Antibacterial agent

Copolymerization of azobenzene-bearing Monomer and 3,4-Ethylenedioxythiophene(EDOT): Improved Electrochemical Performance for Electrochromic Device Applications

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Chinese Journal of Polymer Science 2020年第2期38卷 109-117,I0004页

作者： Serife O.Hacioglu Iskenderun Technical University Department of Engineering Science

In this study,novel electrochromic copolymers of 3,4-ethylenedioxythiophene(EDOT)and(E)-1,2-bis(2-fluoro-4-(4-hexylthiophen-2-yl)phenyl)diazene(M1)with different monomer feed ratios were designed and synthesized electrochemically.Electrochemical and spectroelectrochemical characterizations were performed using voltammetry and UV-Vis-NIR spectrophotometry techniques to test the applicability of copolymers for electrochromic applications.In terms of electrochemical behaviors,addition of an electron-rich EDOT unit into the azobenzenecontaining copolymer increased the electron density on the polymer chain and afforded copolymers with very low oxidation potentials at around0.30 V.While the homopolymers(P1 and PEDOT)exhibited neutral state absorptions centered at 510 and 583 nm,EDOT-bearing copolymers showed red shifted absorptions compared to those of P1 with narrower optical band gaps.In addition,the poor optical contrast and switching times of azobenzene-bearing homopolymer were significantly improved with EDOT addition into the copolymer chain.As a result of the promising electrochromic and kinetic preperties,Co P1.5-bearing single layer electrochromic device that works between purple and light greenish blue colors was constructed and characterized.

关键词： azobenzene EDOT Copolymerization Electrochromic device