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
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
As one of the most representative bioorthogonal reactions,the copper(I)-catalyzed azide-alkyne cycloaddition(CuAAC)reaction has attracted considerable attention in biomedical applications,attributed to its high effici...As one of the most representative bioorthogonal reactions,the copper(I)-catalyzed azide-alkyne cycloaddition(CuAAC)reaction has attracted considerable attention in biomedical applications,attributed to its high efficiency and selectivity for the in situ synthesis of drugs within tumor cells.However,effectively achieving tumor-targeted drug activation through the CuAAC reaction still remains a major challenge,and an efficient delivery system is also needed for the prodrugs to avoid the rapid metabolism within biological environments.In this study,the inactive prodrug precursors were encapsulated within hydrogen-bonded organic framework(HOF)nanoparticles,and then selectively activated in the tumor microenvironment via an intracellular CuAAC reaction.The in situ formed drugs could effectively kill the cancer cells and suppress tumor growth.This strategy enables precise,in situ synthesis of active drug molecules within cancer cells,thereby achieving targeted therapeutic activation while minimizing off-target toxicity to normal tissues and cells.展开更多
Earth-abundant nanocatalysts are actively searched to replace expensive noble metal catalysts for a number of essential processes.Here,Cu catalysts have been designed based on manganese oxide octahedral molecular siev...Earth-abundant nanocatalysts are actively searched to replace expensive noble metal catalysts for a number of essential processes.Here,Cu catalysts have been designed based on manganese oxide octahedral molecular sieve(OMS-2)supports to optimize the catalytic activity in nitrophenol reduction,CuAAC click reaction and terminal alkyne homocoupling.展开更多
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
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
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.
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.
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 Guangxi Technology Base and Talent Subject(GUIKE AD24010020)Central Government Guiding Local Science and Technology Development Projects(GUIKE ZY23055036)the National Natural Science Foundation of China(NSFC 22261006).
文摘As one of the most representative bioorthogonal reactions,the copper(I)-catalyzed azide-alkyne cycloaddition(CuAAC)reaction has attracted considerable attention in biomedical applications,attributed to its high efficiency and selectivity for the in situ synthesis of drugs within tumor cells.However,effectively achieving tumor-targeted drug activation through the CuAAC reaction still remains a major challenge,and an efficient delivery system is also needed for the prodrugs to avoid the rapid metabolism within biological environments.In this study,the inactive prodrug precursors were encapsulated within hydrogen-bonded organic framework(HOF)nanoparticles,and then selectively activated in the tumor microenvironment via an intracellular CuAAC reaction.The in situ formed drugs could effectively kill the cancer cells and suppress tumor growth.This strategy enables precise,in situ synthesis of active drug molecules within cancer cells,thereby achieving targeted therapeutic activation while minimizing off-target toxicity to normal tissues and cells.
基金support from the National Natural Science Foundation of China(No.21805166)the 111 Project of Hubei Province(No.2018-19-1)+1 种基金the Youth Innovation Promotion Association CAS(2018456)Sponsored by Research Fund for Excellent Dissertation of China Three Gorges University,the University of Bordeaux and the Centre National de la Recherche Scientifique(CNRS)is gratefully acknowledged.
文摘Earth-abundant nanocatalysts are actively searched to replace expensive noble metal catalysts for a number of essential processes.Here,Cu catalysts have been designed based on manganese oxide octahedral molecular sieve(OMS-2)supports to optimize the catalytic activity in nitrophenol reduction,CuAAC click reaction and terminal alkyne homocoupling.
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.
