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Click Chemistry

The term "click chemistry" was introduced by K. Barry Sharpless et al. and denotes the development of a set of powerful, highly reliable, and selective reactions for the rapid synthesis of useful new compounds and combinatorial libraries through heteroatom links. Their Review in Angewandte Chemie in 2001 still ranks among the most accessed online articles in the journal.

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Thiol–Ene Clickable Gelatin: A Platform Bioink for Multiple 3D Biofabrication Technologies

Thiol–Ene Clickable Gelatin: A Platform Bioink for Multiple 3D Biofabrication Technologies

Allylated gelatin as a thiol–ene clickable bioink platform provides application for distinct biofabrication techniques. Cross-linking of this cytocompatible system results in controlled homogeneous dimerized networks without additional nondegradable components, in contrast to conventional free radical polymerization. Moreover, UV- and visible-light initiation of the hydrogels are compared.

[Communication]
Sarah Bertlein, Gabriella Brown, Khoon S. Lim, Tomasz Jungst, Thomas Boeck, Torsten Blunk, Joerg Tessmar, Gary J. Hooper, Tim B. F. Woodfield, Juergen Groll
Adv. Mater., October 17, 2017, https://doi.org/10.1002/adma.201703404 Read article

Synthesis of Novel Bis-Triazolyl Glycoconjugates via Dual Click Reaction for the Selective Recognition of Cu(II) Ions

Synthesis of Novel Bis‐Triazolyl Glycoconjugates via Dual Click Reaction for the Selective Recognition of Cu(II) Ions

Glycosyl-β-azidoester, obtained from corresponding olefinic ester via one-pot tandem Michael-Diazotransfer reaction, on clicking with di-O-propargylated ethers afforded high yields of novel bis-triazolyl glycoconjugates. One of the developed bis-triazolyl glycoconjugate 7 a has been sucessfully explored as a promissing sensor for the selective recognition of Cu2+ ions. The probe S1 displayed moderate selective detection of Cu2+ ions by means of ultraviolet spectroscopy. The Job plot experiment suggested 1:1 complexation of probe with Cu2+ ions having a detection limit of 8.00 μM.

[Communication]
Amrita Mishra, Vinod K. Tiwari
ChemistrySelect, October 16, 2017, https://doi.org/10.1002/slct.201702033 Read article

Photoluminescence Lifetime Imaging of Synthesized Proteins in Living Cells Using an Iridium–Alkyne Probe

Photoluminescence Lifetime Imaging of Synthesized Proteins in Living Cells Using an Iridium–Alkyne Probe

It takes a lifetime: A novel bioorthogonal probe, an Ir-alkyne complex, was designed and synthesized. It showed deep-red to near-IR emission and unexpected large lifetime shifts of 414 ns before and after click reaction. This probe enabled the wash-free imaging of the newly synthesized proteins within living cells. NP=nanoparticle.

[Communication]
Jinyu Wang, Jie Xue, Zihe Yan, Sichun Zhang, Juan Qiao, Xinrong Zhang
Angew. Chem. Int. Ed., October 13, 2017, https://doi.org/10.1002/anie.201708566 Read article

Functionalized Graphene Obtained via Thiol-Ene Click Reactions as an Efficient Electrochemical Sensor

Functionalized Graphene Obtained via Thiol‐Ene Click Reactions as an Efficient Electrochemical Sensor

Functionalized graphene/gold nanoparticles (AuNPs) nanocomposite with high sensitivity and good selectivity for the simultaneous determination of uric acid (UA) and folic acid (FA) was prepared, and functionalized graphene (GR-Cys) is synthesized by the thiol-ene click reactions of cysteamine onto the surface of graphene.

[Full Paper]
Yali Li, Lin Bao, Qiulan Zhou, Encai Ou, Weijian Xu
ChemistrySelect, October 12, 2017, https://doi.org/10.1002/slct.201700659 Read article

Click and Click-Inspired Chemistry for the Design of Sequence-Controlled Polymers

Click and Click‐Inspired Chemistry for the Design of Sequence‐Controlled Polymers

Click-inspired reactions have been shown to be powerful chemistry platforms for the synthesis of sequence-controlled polymers. Such precision polymers are actually pushing the application boundaries of synthetic polymers further than ever.

[Review]
Steven Martens, Joshua O. Holloway, Filip. E. Du Prez
Macromol. Rapid Commun., October 09, 2017, https://doi.org/10.1002/marc.201700469 Read article

One-Pot Multicomponent Synthesis of Glycopolymers through a Combination of Host–Guest Interaction, Thiol-ene, and Copper-Catalyzed Click Reaction in Water

One‐Pot Multicomponent Synthesis of Glycopolymers through a Combination of Host–Guest Interaction, Thiol‐ene, and Copper‐Catalyzed Click Reaction in Water

Polyrotaxane (PR)-based heteroglycopolymers, armored with different sugar and fluorescent moieties, are prepared through a one-pot method with a combination of host–guest interaction, thiol-ene, and copper-catalyzed click chemistry in water, and the glycopolymers present good lectin and bacteria binding abilities.

[Communication]
Xiang Hu, Jinbo Gao, Yan Luo, Ting Wei, Yishi Dong, Gaojian Chen, Hong Chen
Macromol. Rapid Commun., September 01, 2017, https://doi.org/10.1002/marc.201700434 Read article

The Effect of Proximal Functionality on the Allylic Azide Equilibrium

The Effect of Proximal Functionality on the Allylic Azide Equilibrium

This work describes the first systematic evaluation of proximal functionality's effect on the equilibrium constant of the allylic azide rearrangement. We report three series of allylic azides to describe the equilibrium of hydroxy-crotyl azide.

[Communication]
Mary H. Packard, James H. Cox, Victoria P. Suding, Joseph J. Topczewski
Eur. J. Org. Chem., September 01, 2017, https://doi.org/10.1002/ejoc.201700693 Read article

Thiol–Ene (Click) Reactions as Efficient Tools for Terpene Modification

Thiol–Ene (Click) Reactions as Efficient Tools for Terpene Modification

Clicking terpenes: This Focus Review covers the development of thiol–ene (click) chemistry for the preparation of platform chemicals, monomers, and polymers derived from terpenes. The use of this reaction has led to various advanced applications.

[Focus Review]
Maulidan Firdaus
Asian J. Org. Chem., August 29, 2017, https://doi.org/10.1002/ajoc.201700387 Read article

In-Situ Generated and Premade 1-Copper(I) Alkynes in Cycloadditions

In‐Situ Generated and Premade 1‐Copper(I) Alkynes in Cycloadditions

Based on the investigation of the references and our works on CuAAC reaction, we found the difference and conversion between the in-situ generated and the premade 1-copper(I) alkynes. Finally, the novel carboxylic acid-promoted CuAAC strategy was developed, which has been proven to be the most convenient and highly efficient CuAAC method to date. Furthermore, the novel function of the premade 1-copper(I) alkynes as excellent dipolarophiles was first disclosed and applied. In this article, a series of works reported by our group for the in-situ generated and the premade 1-copper(I) alkynes in cycloadditions are reviewed.

[Personal Account]
Xinyan Wang, Xingyong Wang, Xuesong Wang, Jianlan Zhang, Chulong Liu, Yuefei Hu
Chem. Rec., June 22, 2017, https://doi.org/10.1002/tcr.201700011 Read article

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