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Control of selectivity in organic synthesis via heterogeneous photocatalysis under visible light

Nano Research Energy 2022年第1期1卷 90-109页

作者： Yitao Dai Yujie Xiong Suzhou Institute for Advanced Research University of Science and Technology of ChinaSuzhou 215123China School of Chemistry and Materials Science University of Science and Technology of ChinaHefei 230026China

Organic synthesis driven by heterogeneous catalysis is a central research theme to both fundamental research and industrial production of fine ***,the employment of stoichiometric strong oxidizing or reducing reagents(e.g.,K_(2)Cr_(2)O_(7) and LiAlH_(4))and harsh reaction conditions(e.g.,high temperature and pressure)always leads to the products of overreaction and other by-product residues(e.g.,salt and acid waste).Thus the poor control of product selectivity and tremendous energy consumption result in the urgent demand to develop novel technologies for heterogeneous *** the current global theme of development in CO_(2) reduction and sustainable energy utilization,one promising protocol is heterogeneous *** enables sustainable solar-to-chemical energy conversion under mild conditions(e.g.,room temperature,ambient pressure,and air as the oxidant)and offers unique reaction pathways for improved selectivity *** accurately tailor the selectivity of desired products,the electronic structure(e.g.,positions of valence-band maximum and conduction-band minimum),geometric structure(e.g.,nanorod,nanosheet,and porous morphology),and surface chemical micro-environment(e.g.,vacancy sites and co-catalysts)of heterogeneous photocatalysts require rational design and *** this review,we will briefly analyze some effective photocatalytic systems with the excellent regulation ability of product selectivity in organic transformations(mainly oxidation and reduction types)under visible light irradiation,and put forward opinions on the optimal fabrication of nanostructured photocatalysts to realize selective organic synthesis.

关键词： organic synthesis selectivity control heterogeneous photocatalysis photocatalyst design visible light irradiation

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Solar-assisted photocatalytic water splitting using defective UiO-66 solids from modulated synthesis

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Nano Research 2024年第5期17卷 4134-4150页

作者： Celia M.Rueda-Navarro María Cabrero-Antonino Paula Escamilla Valentín Díez-Cabanes Dong Fan Pedro Atienzar Belén Ferrer Ignacio Vayá Guillaume Maurin Herme G.Baldoví Sergio Navalón Departamento de Química Universitat Politècnica de ValènciaCamino de Vera s/nValencia 46022Spain Instituto de Ciencia Molecular(ICMOL) Universitat de ValènciaPaterna 46980Spain ICGM Univ.MontpellierCNRSENSCMMontpellier34095France Instituto de Tecnología Química(UPV-CSIC) Universitat Politècnica de ValènciaAvenida de los Naranjos s/nValencia 46022Spain

Metal-organic frameworks(MOFs)are attracting increasing interests as photocatalysts for solar-driven hydrogen production from *** paper reports on a comparative study of using either acetic acid(AA)or trifluoroacetic acid(TFA)as the representative UiO-66 organic modulators for synthesizing visible light responsive UiO-66(Zr)-X(X:NH_(2) or NO_(2))photocatalysts for water *** results show that photocatalytic hydrogen generation from a water/methanol mixture can be improved by varying the nature and amount of the modulator employed to prepare the different UiO-66(Zr)-X(X:NH_(2) or NO_(2))solid ***-66(Zr)-NH_(2) was the most active photocatalyst,followed by UiO-66(Zr)-NO_(2),both prepared with 12 equivalents of AA with respect to the organic *** UiO-66(Zr)-NH_(2) solid was more active than the parent MOF in photocatalytic overall water splitting(OWS)(H_(2) and O_(2) production of 450 and 160μmol·g^(-1),respectively,in 5 h;apparent quantum yield(AQY)at 400 nm of 0.06%)in the absence of methanol and compares favourably with analogous *** on the photocatalytic activity of the most active solids of both series was obtained by means of a series of techniques,including ultraviolet-visible(UV-vis)diffuse reflectance,X-ray photoelectron spectroscopy(XPS),laser flash photolysis(LFP),electron spin resonance(ESR),photoluminescence and photoelectrochemical measurements together with density functional theory(DFT)*** results showed that organic acid modulators can be used to enhance the photocatalytic activity of missing linker UiO-66 defective materials in solar-powered water splitting.

关键词： heterogeneous photocatalysis metal-organic frameworks(MOFs) UiO-66 materials carboxylic acid modulators water splitting solar light

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Organic photocatalysts:From molecular to aggregate level

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Nano Research 2022年第5期15卷 3835-3858页

作者： Chuxuan Yan Jiaqi Dong Yingzhi Chen Wenjie Zhou Yu Peng Yue Zhang Lu-ning Wang School of Materials Science and Engineering University of Science and Technology BeijingBeijing 100083China Shunde Graduate School of University of Science and Technology Beijing Foshan 528399China

Organic semiconductors(OSCs)have the advantages of tunable molecular structures,suitable band gaps,and exceptional optoelectronic *** π-π stacking ability of OSCs also leads to appealing molecular stacking structure,function,and *** far,organic photocatalysts have engaged in homogeneous or heterogeneous photocatalysis in the form of free molecules,supported molecules,or ***,researches on organic photocatalysts have expanded from small organic molecules to the organic macromolecules,as well as their various nanostructures and nanocomposites including isolated zero-dimensional(0D),one-dimensional(1D),two-dimensional(2D),three-dimensional(3D)nanostructures,and their ***,many versatile strategies have been explored to improve photocatalytic ability and practicality either from molecular synthetic modification,crystal,or interface *** this review,we first discuss the photophysical and photochemical processes of organic photocatalysts that govern the ultimate photocatalytic efficiency;we then summarize different forms of organic photocatalysts,their rational design strategies,and mechanistic pathways,as well as their applications in H_(2) evolution,CO_(2) reduction,and environmental purification,aiming to highlight the structure/property relationships;we lastly propose ongoing directions and challenges for future development of organic photocatalysts in real use.

关键词： organic photocatalyst homogeneous photocatalysis heterogeneous photocatalysis nanostructure heterostructure

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Iron sites on defective BiOBr nanosheets:Tailoring the molecular oxygen activation for enhanced photocatalytic organic synthesis

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Nano Research 2022年第2期15卷 1509-1516页

作者： Xinhui Ye Yu Li Peipei Luo Bingcai He Xinxing Cao Tongbu Lu MOE International Joint Laboratory of Materials Microstructure Institute for New Energy Materials and Low Carbon TechnologiesSchool of Materials Science and EngineeringTianjin University of TechnologyTianjin 300384China

Sunlight-driven activation of molecular oxygen(O_(2))for organic oxidation reactions offers an appealing strategy to cut down the reliance on fossil fuels in chemical industry,yet it remains a great challenge to simultaneously tailor the charge kinetics and promote reactant chemisorption on semiconductor catalysts for enhanced photocatalytic ***,we report iron sites immobilized on defective BiOBr nanosheets as an efficient and selective photocatalyst for activation of O_(2) to singlet oxygen(^(1)O_(2)).These Fe^(3+) species anchored by oxygen vacancies can not only facilitate the separation and migration of photogenerated charge carrier,but also serve as active sites for effective adsorption of ***,low-temperature phosphorescence spectra combined with X-ray photoelectron spectroscopy(XPS)and electronic paramagnetic resonance(EPR)spectra under illumination reveal that the Fe species can boost the quantum yield of excited triplet state and accelerate the energy transfer from excited triplet state to adsorbed O2 via a chemical loop of Fe^(3+)/Fe^(2+),thereby achieving highly efficient and selective generation of ^(1)O_(2).As a result,the versatile iron sites on defective BiOBr nanosheets contributes to near-unity conversion rate and selectivity in both aerobic oxidative coupling of amines to imines and sulfoxidation of organic *** work highlights the significant role of metal sites anchored on semiconductors in regulating the charge/energy transfer during the heterogeneous photocatalytic process,and provides a new angle for designing high-performance photocatalysts.

关键词： iron site oxygen vacancy molecular oxygen activation singlet oxygen heterogeneous photocatalysis selective oxidation

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heterogeneous photocatalytic borylation of aryl iodides mediated by isoreticular 2D covalent organic frameworks

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Chinese Chemical Letters 2023年第5期34卷 594-597页

作者： Pengna Shang Xiaoli Yan Yang Li Junji Liu Guang Zhang Long Chen Department of Chemistry and Tianjin Key Laboratory of Molecular Optoelectronic Science Tianjin UniversityTianjin 300072China State Key Laboratory of Supramolecular Structure and Materials College of ChemistryJilin UniversityChangchun 130012China

Metal-free heterogeneous photocatalysts provide an environmental-friendly and cost-efficient avenue for green organic *** organic frameworks(COFs)as heterogeneous photocatalysts showcase promising potential in the field of photocatalytic organic reactions due to their high porosity,insolubility and tailor-made ***,thus far,COF-based catalysts only mediated a few types of ***,we developed a series of isoreticular nitrogen-rich covalent organic frameworks(N-COFs)with comparable porous structures as photocatalysts which effectively mediated the borylation of aryl iodides with broad substrate ***,6N-COF exhibits excellent photocatalytic efficiency and superior *** suggests a new pathway to construct efficient heterogeneous photocatalysts for the borylation of aryl halides.

关键词： Covalent organic frameworks Nitrogen-rich heterogeneous photocatalysis Borylation Green organic synthesis

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Photo-induced surface frustrated Lewis pairs for promoted photocatalytic decomposition of perfluorooctanoic acid

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Frontiers of Environmental Science & Engineering 2023年第1期17卷 27-32页

作者： Xianjun Tan Zhenying Jiang Yuxiong Huang Tsinghua-Berkeley Shenzhen Institute(TBSI) Shenzhen International Graduate SchoolTsinghua UniversityShenzhen 518055China

heterogeneous photocatalysis has gained substantial research interest in treating per-and polyfluoroalkyl substances(PFAS)-contaminated ***,sluggish degradation kinetics and low defluorination efficiency compromise their practical ***,we report a superior photocatalyst,defected Bi_(3)O(OH)(PO_(4))_(2),which could effectively degrade typical PFAS,perfluorooctanoic acid(PFOA),with high defluorination *** UV light irradiation could in situ generate oxygen vacancies on Bi_(3)O(OH)(PO_(4))_(2) through oxidation of the lattice hydroxyls,which further promotes the formation of Lewis acidic coordinately unsaturated bismuth ***,the Lewis acidic sites couple with the proximal surface hydroxyls to constitute the surface frustrated Lewis pairs(SFLPs).With the in-depth spectroscopic analysis,we revealed that the photo-induced SFLPs act as collection centers to effectively adsorb PFOA and endow accessible pathways to transfer photogenerated holes to PFOA ***,activation of the terminal carboxyl,a ratelimiting step for PFOA decomposition,could be easily achieved over the defected Bi_(3)O(OH)(PO_(4))_(2) *** results suggest that SFLPs exhibit great potential in developing highly efficient photocatalysts to degrade persistent organic pollutants.

关键词： heterogeneous photocatalysis Surface frustrated Lewis pairs Perfluorooctanoic acid Defluorination efficiency Environmental remediation

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Donor-acceptor 2D covalent organic frameworks for efficient heterogeneous photocatalyticα-oxyamination

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Science China Chemistry 2021年第5期64卷 827-833页

作者： Huan Liu Xiaoli Yan Weiben Chen Zhen Xie Shen Li Weihua Chen Ting Zhang Guolong Xing Long Chen Department of Chemistry Institute of Molecular PlusTianjin Key Laboratory of Molecular Optoelectronic ScienceTianjin UniversityTianjin 300072China College of Chemistry and Green Catalysis Center Zhengzhou UniversityZhengzhou 450001China

Covalent organic frameworks(COFs)have received widespread interest due to their high porosity,excellent crystallinity,tailorable structures,and broad application *** has been demonstrated that proper combination and arrangement of electron donor and acceptor units in 2D conjugated COF lattice could promote efficient charge separation and electron transfer,and thus is beneficial for *** this article,three donor-acceptor(D-A)2D COFs were prepared by Schiff base reaction of electron acceptor 4,4′,4′′,4′′′-(benzo[1,2-d:4,5-d′]bis(oxazole)-2,4,6,8-tetrayl)tetraaniline(BBO)with different electron donors:thieno[3,2-b]thiophene-2,5-dicarbaldehyde(TT),benzo[1,2-b:4,5-b’]dithiophene-2,6-dicarboxaldehyde(BDT)and terephthalaldehyde(Ph),*** D-A 2D COFs exhibited prominent photocatalytic activity towardsα-oxyamination of 1,3-dicarbonyl with 2,2,6,6-tetramethyl-1-piperdinyloxy(TEMPO)upon visible light *** these D-ABBO-COFs,DTT-ABBO-COF exhibited the highest photocatalytic rates,which can be ascribed to the more negative highest occupied molecular orbital(HOMO)and narrower *** excellent stability,high activity and superior recyclability render DTT-ABBO-COF as a potential and environmentally friendly heterogeneous catalyst forα-oxyamination.

关键词： covalent organic frameworks donor-acceptor benzodioxazole heterogeneous photocatalysis α-oxyamination

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Selective CO_(2) reduction into formate using Ln-Ta oxynitrides combined with a binuclear Ru(Ⅱ)complex under visible light

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Journal of Energy Chemistry 2021年第4期30卷 176-182页

作者： Kanemichi Muraoka Miharu Eguchi Osamu Ishitani Francois Chevire Kazuhiko Maeda Department of Chemistry School of ScienceTokyo Institute of TechnologyMeguro-ku152-8550 TokyoJapan Japan Society for the Promotion of Science Chiyoda-ku102-0083 TokyoJapan Research Center for Functional Materials National Institute for Materials ScienceTsukuba 305-0044IbarakiJapan Univ Rennes CNRSISCR-UMR 6226Rennes F-35000France

Hybrid materials constructed from a visible-light-absorbing semiconductor and a functional metal complex have attracted attention as efficient photocatalysts for CO_(2) reduction with high selectivity to a desired *** this work,defect fluorite-type Ln-Ta oxynitrides LnTaO_(x)N_(y)(Ln=Nd,Sm,Gd,Tb,Dy and Ho)were examined as the semiconductor component in a hybrid photocatalyst system combined with known Ag nanoparticle promoter and binuclear ruthenium(Ⅱ)complex(RuRu’).Among the LnTaO_(x)N_(y) examined,TbTaO_(x)N_(y) gave the highest performance for CO_(2) reduction under visible light(k>400 nm),with a Ru Ru0-based turnover number of 18 and high selectivity to formate(>99%).Physicochemical analyses indicated that high crystallinity and more negative conduction band potential of Ln Ta O_(x)N_(y)with the absence of Ln-4 f states in the band gap structure contributed to higher activity of the hybrid photocatalyst.

关键词： Artificial photosynthesis heterogeneous photocatalysis Mixed anion compounds Solar fuels

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Effect of transition metaldoping under reducing calcination atmosphere on photocatalytic property of TiO_2 immobilized on SiO_2 beads

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Journal of Environmental Sciences 2013年第7期25卷 1419-1423页

作者： Rumi Chand Eiko Obuchi Katsumi Katoh Hom Nath Luitel Katsuyuki Nakano Department of Chemical Engineering Fukuoka University Department of Applied Chemistry Saga University

TiO2 immobilized on SiO2 （TiO2 /SiO2 ） have been prepared by sol-gel method and various ions of transition metals （Cr3＋ , Co2＋ , Ni2＋ , Cu2＋ , and Zn2＋）weredoped on the photocatalyst usingwet impregnation method under reducing calcination atmosphere. The photocatalytic activity of metaldoped TiO2 /SiO2 towards phenoldegradation under black light irradiationwere investigated and comparedwith undoped TiO2 /SiO2 . The results showed that the photoresponse of Cu2＋ and Zn2＋doped TiO2 /SiO2were larger than undoped TiO2 /SiO2 , indicating that the photogenerated carrierswere separated more efficiently in Cu2＋ and Zn2＋doped TiO2 /SiO2 . The reactivitywas in the order of Cu2＋〉 Zn2＋〉 Ni2＋〉 Cr3＋〉 Co2＋ . Thedifferent photoreactivitywas ascribed to combine effect of thedifferent ionic radii and photocorrison tendency of thedopants. The samplewas also characterized by surface analytical methods such as X-raydiffraction, scanning electron micrograph/electrondispersive X-ray analyzer and UV-Vis absorption spectrum.

关键词： heterogeneous photocatalysis TiO2 SiO2 beads metaldoping photodecomposition

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Pillar[5]arene based conjugated macrocycle polymers with unique photocatalytic selectivity

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Chinese Chemical Letters 2020年第12期31卷 3225-3229页

作者： Hui Qiang Tao Chen Zhuo Wang Wenqian Li Yunzhe Guo Jie Yang Xueshun Jia Hui Yang Weibo Hu Ke Wen College of Science Shanghai universiryShanghai 200444China Shanghai Advanced Research Intstitute Chinese Academy of SciencesShanghai 201210China University of Chinese Acadeny of Sciences Beijing 100049China School of Physicnl Science and Technology ShanghaiTech UniversityShanghai 201210China

The development of heterogeneous catalysts with substrate shape,size or electronic constitution selectivity is a huge challenge in *** herein is a host-guest interaction strategy to endow photocatalysts with special *** adjusting the precursors,conjugated macrocycle polymers(CMPs)with pillar[5]arene struts(CMP-1 and CMP-2)and a corresponding non-pillar[5]are necontained conjugated organic polymer(COP-1)were prepared and the photocatalytic activities toward sulfide derivatives were *** sulfides showed similar conve rsions when COP-1 was used as a photocatalyst,but exhibited significant differences when it turned to the ***,the conversion yield of S-1 achieved near 18 folds over the one of S-2 when CMP-2 was used as a *** studies confirmed that the"host-guest"effect of pillar[5]arene struts in CMPs was the main cause of the *** present work establishes CMPs as novel heterogeneous photocatalysts with substrate selectivity,and such a method will inspire the researchers concerning preparation of heterogeneous catalysts with excellent selectivity.

关键词： heterogeneous photocatalysis Selectivity Host-guest Pillararene Sulfide

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