Cu (I) catalyzed alkyne-azide cycloaddition (CuAAC) reaction,a typical "click" reaction,is one of the modular synthetic approaches which has been broadly used in various organic syntheses,medicinal chemistry...Cu (I) catalyzed alkyne-azide cycloaddition (CuAAC) reaction,a typical "click" reaction,is one of the modular synthetic approaches which has been broadly used in various organic syntheses,medicinal chemistry,materials development and bioconjugation applications.We have for the first time synthesized two dialkyne derivatized fluorescent crosslinkers which could be applied to crosslink two biomolecules using CuAAC reaction.Turnip yellow mosaic virus,a plant virus with unique structural and chemical properties,was used as a prototypical scaffold to form a 2D single layer at the interface of two immiscible liquids and crosslinked with these two linkers by the CuAAC reaction.Upon crosslinking,the fluorescence of both linkers diminished,likely due to the distortion of the polymethylene backbone,which therefore could be used to indicate the completion of the reaction.展开更多
Metal contamination is a waste-generating and serious issue in the synthesis of chemicals,in particular in the case of products with biological activity.The appropriate selection of operating conditions plays a crucia...Metal contamination is a waste-generating and serious issue in the synthesis of chemicals,in particular in the case of products with biological activity.The appropriate selection of operating conditions plays a crucial role in the abatement of metal leaching in solution and associated wastes.Herein we report a waste-minimized continuous flow process for the synthesis of 1,4-disubstitutedβ-keto 1,2,3-triazoles exploiting the use of a copper tube flow reactor(CTFR).The selection of the proper azeotropic mixture allowed an almost quantitative recovery of the reaction medium greatly influencing the E-factor of the protocol.A thorough understanding of the main parameters affecting the waste generation was given by calculation of the E-factor distribution for different work-up tested under batch and flow conditions.Furthermore,the measurement of different green metrics(AE:Atom Economy,SF:Stoichiometric Factor,RME:Reaction Mass Efficiency,and MRP:Mass Recover Parameter)clearly demonstrated the benefits of the flow scale-up that allowed to perform a low environmental footprint CuAAC reaction.展开更多
Borondipyrromethenes(BODIPY) are a class of fluorescent dyes whose fluorescence quantum yields are generally high and independent of the solvent.In this paper,we report the synthesis of a new type of BODIPY compound t...Borondipyrromethenes(BODIPY) are a class of fluorescent dyes whose fluorescence quantum yields are generally high and independent of the solvent.In this paper,we report the synthesis of a new type of BODIPY compound that carries an azido group on the 3-position of the pyrrole core.The azido group quenches the fluorescence of the dye due to its weak electron-donating effect.The fluorescence of the BODIPY dye can be switched on after reacting with alkynes via a Cu(Ⅰ) catalyzed azide-alkyne cycloaddition(CuAAC) reaction.We further demonstrate that this azido-BODIPY compound can be used in the cell imaging applications.展开更多
Chiral-polymers with metal-coordination ability showgreat potential formediating asymmetric reactions.However,the synthesis of structurally diverse chiral polymers remains a great challenge,especially doing so efficie...Chiral-polymers with metal-coordination ability showgreat potential formediating asymmetric reactions.However,the synthesis of structurally diverse chiral polymers remains a great challenge,especially doing so efficiently.Herein,four types of Cucatalyzed multicomponent asymmetric polymerizationswere developed using a flexible combination of OBoc-alkyne.展开更多
Cyclic polymers have attracted more and more attentions in recent years because of their unique topological structures and characteristic properties in both solution and bulk state. There are relatively few reports on...Cyclic polymers have attracted more and more attentions in recent years because of their unique topological structures and characteristic properties in both solution and bulk state. There are relatively few reports on cyclic polymers, partly because of the more demanding synthetic procedures. In recent years, 'click' reaction, especially Cu(I)-catalyzed azide-alkyne cycloaddition(CuAAC), has been widely utilized in the synthesis of cyclic polymer materials because of its high efficiency and low susceptibility to side reactions. In this review, we will focus on three aspects:(1) Constructions of monocyclic polymer using CuAAC 'click' chemistry;(2) Formation of complex cyclic polymer topologies through CuAAC reactions;(3) Using CuAAC 'click' reaction in the precise synthesis of molecularly defined macrocycles. We believe that the CuAAC click reaction is playing an important role in the design and synthesis of functional cyclic polymers.展开更多
Borondipyrromethenes(BODIPY) are a class of fluorescent dyes whose fluorescence quantum yields are generally high and independent of the solvent.In this paper,we report the synthesis of a new type of BODIPY compound t...Borondipyrromethenes(BODIPY) are a class of fluorescent dyes whose fluorescence quantum yields are generally high and independent of the solvent.In this paper,we report the synthesis of a new type of BODIPY compound that carries an azido group on the 3-position of the pyrrole core.The azido group quenches the fluorescence of the dye due to its weak electron-donating effect.The fluorescence of the BODIPY dye can be switched on after reacting with alkynes via a Cu(I) catalyzed azide-alkyne cycloaddition(CuAAC) reaction.We further demonstrate that this azido-BODIPY compound can be used in the cell imaging applications.展开更多
基金We are grateful for the support from the US NSF CAREER Award (CHE-0748690)US DoD–ARO (W911NF-09-1-0236), US DoE+4 种基金the W. M. Keck Foundationthe Camille Dreyfus Teacher-Scholarshipthe Alfred P. Sloan Foundationthe National Natural Science Foundation of China (50673025)the National Basic Research 973 Program (2006CB806200)
文摘Cu (I) catalyzed alkyne-azide cycloaddition (CuAAC) reaction,a typical "click" reaction,is one of the modular synthetic approaches which has been broadly used in various organic syntheses,medicinal chemistry,materials development and bioconjugation applications.We have for the first time synthesized two dialkyne derivatized fluorescent crosslinkers which could be applied to crosslink two biomolecules using CuAAC reaction.Turnip yellow mosaic virus,a plant virus with unique structural and chemical properties,was used as a prototypical scaffold to form a 2D single layer at the interface of two immiscible liquids and crosslinked with these two linkers by the CuAAC reaction.Upon crosslinking,the fluorescence of both linkers diminished,likely due to the distortion of the polymethylene backbone,which therefore could be used to indicate the completion of the reaction.
基金support to the project AMIS,through the program“Dipartimenti di Eccellenza-2018-2022”.
文摘Metal contamination is a waste-generating and serious issue in the synthesis of chemicals,in particular in the case of products with biological activity.The appropriate selection of operating conditions plays a crucial role in the abatement of metal leaching in solution and associated wastes.Herein we report a waste-minimized continuous flow process for the synthesis of 1,4-disubstitutedβ-keto 1,2,3-triazoles exploiting the use of a copper tube flow reactor(CTFR).The selection of the proper azeotropic mixture allowed an almost quantitative recovery of the reaction medium greatly influencing the E-factor of the protocol.A thorough understanding of the main parameters affecting the waste generation was given by calculation of the E-factor distribution for different work-up tested under batch and flow conditions.Furthermore,the measurement of different green metrics(AE:Atom Economy,SF:Stoichiometric Factor,RME:Reaction Mass Efficiency,and MRP:Mass Recover Parameter)clearly demonstrated the benefits of the flow scale-up that allowed to perform a low environmental footprint CuAAC reaction.
基金supported by the Alfred P. Sloan Scholarship, Camille Dreyfus Teacher Scholar Award,the W.M.Keck Foundation,and the Colon Cancer Center of University of South Carolinasupport from the National Natural Science Foundation of China(91013006)
文摘Borondipyrromethenes(BODIPY) are a class of fluorescent dyes whose fluorescence quantum yields are generally high and independent of the solvent.In this paper,we report the synthesis of a new type of BODIPY compound that carries an azido group on the 3-position of the pyrrole core.The azido group quenches the fluorescence of the dye due to its weak electron-donating effect.The fluorescence of the BODIPY dye can be switched on after reacting with alkynes via a Cu(Ⅰ) catalyzed azide-alkyne cycloaddition(CuAAC) reaction.We further demonstrate that this azido-BODIPY compound can be used in the cell imaging applications.
基金supported by the National Science Foundation of China(No.21978039)Special Funds of the Central Government Guiding Local Science and Technology Development(Nos.2021JH6/10500148 and 2021JH6/10500146)+1 种基金the Natural Science Foundation of Jiangsu Province(No.BK20211100)and the Fundamental Research Funds for the Central Universities(Nos.DUT20YG120 and DUT21YG133).
文摘Chiral-polymers with metal-coordination ability showgreat potential formediating asymmetric reactions.However,the synthesis of structurally diverse chiral polymers remains a great challenge,especially doing so efficiently.Herein,four types of Cucatalyzed multicomponent asymmetric polymerizationswere developed using a flexible combination of OBoc-alkyne.
基金financially supported by the National Natural Science Foundation of China(No.21234005)the State and Local Joint Engineering Laboratory for Novel Functional Polymeric Materials,the Priority Academic Program Development of Jiangsu Higher Education Institutions(PAPD)the Program of Innovative Research Team of Soochow University
文摘Cyclic polymers have attracted more and more attentions in recent years because of their unique topological structures and characteristic properties in both solution and bulk state. There are relatively few reports on cyclic polymers, partly because of the more demanding synthetic procedures. In recent years, 'click' reaction, especially Cu(I)-catalyzed azide-alkyne cycloaddition(CuAAC), has been widely utilized in the synthesis of cyclic polymer materials because of its high efficiency and low susceptibility to side reactions. In this review, we will focus on three aspects:(1) Constructions of monocyclic polymer using CuAAC 'click' chemistry;(2) Formation of complex cyclic polymer topologies through CuAAC reactions;(3) Using CuAAC 'click' reaction in the precise synthesis of molecularly defined macrocycles. We believe that the CuAAC click reaction is playing an important role in the design and synthesis of functional cyclic polymers.
文摘Borondipyrromethenes(BODIPY) are a class of fluorescent dyes whose fluorescence quantum yields are generally high and independent of the solvent.In this paper,we report the synthesis of a new type of BODIPY compound that carries an azido group on the 3-position of the pyrrole core.The azido group quenches the fluorescence of the dye due to its weak electron-donating effect.The fluorescence of the BODIPY dye can be switched on after reacting with alkynes via a Cu(I) catalyzed azide-alkyne cycloaddition(CuAAC) reaction.We further demonstrate that this azido-BODIPY compound can be used in the cell imaging applications.
