Review
Biotechnology & Applied Microbiology
Priyank Purohit, Akanksha Bhatt, Ravi K. Mittal, Magda H. Abdellattif, Thoraya A. Farghaly
Summary: Polymer grafting is a technique to improve the morphology and properties of polymers. By creating copolymers or grafting, the physicochemical properties of polymers can be further modified. This review discusses various chemical approaches for polymer grafting, such as free radical reactions, click reactions, amide formation, and alkylation. The review also covers the importance of the graft-to approaches and their application in different fields.
FRONTIERS IN BIOENGINEERING AND BIOTECHNOLOGY
(2023)
Review
Chemistry, Multidisciplinary
Yiming Liao, Baoqi Wu, Rongzhi Tang, Feng Lin, Yu Tan
Summary: This article reviews the wide application and advantages of SPAAC reaction in fields such as biomedicine and materials science. The stability and reactivity of cycloalkynes, as well as their reaction rate constants in SPAAC, are discussed. The research progress in the preparation methods of commonly used cyclic alkynes is introduced. Furthermore, the application, challenge, and future outlook of SPAAC without copper catalysis are discussed and prospected.
PROGRESS IN CHEMISTRY
(2022)
Review
Chemistry, Physical
Chang-Qing Qin, Cheng Zhao, Guo-Shu Chen, Yun-Lin Liu
Summary: Catalytic enantioselective azide-alkyne cycloaddition (E-AAC) is an efficient technology for constructing diverse chiral triazoles, with applications in synthetic and medicinal chemistry, biological chemistry, and materials science. Significant developments have been made in copper-, nickel-, iridium-, and rhodium-catalyzed E-AAC reactions in the past six years. This review summarizes these advancements according to different strategies implemented.
Article
Polymer Science
Eric Meichsner, Darryl Fong, Dialia E. M. Ritaine, Alex Adronov
Summary: The study demonstrates the use of SPAAC as a polymerization tool to rapidly prepare a polymer library with diverse thermal and stimulus-responsive properties. The polymerization process does not require heating or catalyst addition, enabling the preservation of sensitive moieties and demonstrating solid- and solution-state stimulus-responsiveness.
JOURNAL OF POLYMER SCIENCE
(2021)
Article
Chemistry, Multidisciplinary
Matt Timmers, Wouter Peeters, Niels J. Hauwert, Cristianne J. F. Rijcken, Tina Vermonden, Ingrid Dijkgraaf, Rob M. J. Liskamp
Summary: This article describes the site-specific attachment of the reactive TMTHSI-click handle to the N-terminus of peptides and proteins. The resulting molecular constructs can be used in strain-promoted azide alkyne cycloaddition (SPAAC) for reaction with azide-containing proteins. The article also discusses the N-terminal specific attachment of the reactive TMTHSI-click handle to peptides and proteins, followed by strain-promoted cycloaddition with azide-containing compounds.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Suguru Yoshida, Yuki Sakata, Yoshihiro Misawa, Takamoto Morita, Tomoko Kuribara, Harumi Ito, Yuka Koike, Isao Kii, Takamitsu Hosoya
Summary: Efficient consecutive formation of 1,2,3-triazoles using multiazide platforms has been achieved in this study. A four-step synthesis of tetrakis(triazoles) was successfully performed from a tetraazide platform molecule, based on the unique clickability of the 1-adamantyl azido group. This method was applied to the convergent synthesis of tetrafunctionalized probes in a modular synthetic manner.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Junbo Wang, Kaifeng Niu, Chaojie Xu, Huaming Zhu, Honghe Ding, Dong Han, Yuanjing Zheng, Jiahao Xi, Sifan You, Chuan Deng, Haiping Lin, Johanna Rosen, Junfa Zhu, Jonas Bjoerk, Qing Li, Lifeng Chi
Summary: On-surface synthesis is a powerful methodology for fabricating low-dimensional functional materials. This study investigates the influence of detailed adsorption configurations on activation energies on different metal surfaces, demonstrating the impact of molecule-substrate interactions on activation barriers.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Atul Kumar, Navaneet Kumar, Deepak Bhadoria
Summary: The first visible-light promoted and photocatalyst-free three-component reaction protocol has been developed to efficiently synthesize 4-functionalized 1,5-disubstituted 1,2,3-triazoles from terminal alkynes, aryl azides, and arylsulfinic acid sodium salts or arylsulfonyl hydrazides in an aqueous medium at room temperature. This reaction offers high regioselectivity, scalability, and good functional group tolerance among its advantages.
Article
Chemistry, Multidisciplinary
Fei-Fei Wang, Jia-Hui Li, Hai-Yan Liu, Shu-Ping Deng, Ying-Ying Liu, Jian-Fang Ma
Summary: Three distinctive coordination polymers were solvothermally synthesized using a resorcin[4]arene ligand. Among them, compound 1 showed efficient and selective catalytic performance, and could be recycled with preservation of its catalytic capability and structural integrity.
NEW JOURNAL OF CHEMISTRY
(2021)
Article
Biology
Z. Soederlund, A. Ibanez-Fonseca, S. Hajizadeh, J. C. Rodriguez-Cabello, J. Liu, L. Ye, E. Tykesson, L. Elowsson, G. Westergren-Thorsson
Summary: The study demonstrates the application of synthetic glycosaminoglycans in inducing desired cellular responses and the possibility of specific growth factor release using a modular 3D scaffold in vitro and in vivo.
COMMUNICATIONS BIOLOGY
(2022)
Article
Chemistry, Organic
T. Moritz Weber, Joerg Pietruszka
Summary: Copper-catalyzed alkyne azide click chemistry (CuAAC) is important for drug development and biological materials labeling. A new tridentate Cu-ligand called TDETA was synthesized as a scalable and non-toxic alternative to HN3 and the previously used DTEA ligand. TDETA showed excellent solubility in organic solvents and aqueous solutions, outcompeted commercial ligands THPTA and TBTA for various azide and alkyne combinations using Cu(I) and Cu(II) species, and had a 80% recovery yield.
SYNTHESIS-STUTTGART
(2023)
Article
Chemistry, Multidisciplinary
Borja Cirera, Alexander Riss, Pingo Mutombo, Jose Urgel, Jose Santos, Marco Di Giovannantonio, Roland Widmer, Samuel Stolz, Qiang Sun, Max Bommert, Roman Fasel, Pavel Jelinek, Willi Auwarter, Nazario Martin, David Ecija
Summary: The design of organometallic complexes is crucial in modern organic chemistry and catalysis. On-surface synthesis has recently emerged as a disruptive method to design compounds and nanomaterials previously considered impossible. The activation of inner diacetylene moieties of a molecular precursor by copper surface adatoms has led to the formation of unprecedented organocopper metallacycles on Cu(111), paving the way for new avenues in organometallic compound engineering and polyyne chemistry on surfaces.
Article
Chemistry, Applied
Shaik Syed Hussain, Kesavarao Sykam, Ramanuj Narayan, Pratyay Basak
Summary: Si-PUTs were prepared by azide-alkyne cycloaddition, showing excellent surface hydrophobicity and anti-corrosion properties. A simple modification of aminopropyl trimethoxy silane produced a dialkyne terminated monomer, while azide-terminated urethane monomers were synthesized using azidoethanol and common diisocyanates. The successful formation of Si-PUTs was confirmed by FTIR and XPS analysis, and their performance as corrosion resistive coatings was evaluated comprehensively.
PROGRESS IN ORGANIC COATINGS
(2023)
Article
Chemistry, Multidisciplinary
Samuel Stolz, Michael Bauer, Carlo A. Pignedoli, Nils Krane, Max Bommert, Elia Turco, Nicolo Bassi, Amogh Kinikar, Nestor Merino-Diez, Roland Hany, Harald Brune, Oliver Groning, Roland Widmer
Summary: This study investigates the impact of chirality transfer and ensemble effect on thermally activated azide-alkyne Huisgen cycloaddition on well-defined and chiral intermetallic PdGa{111} surfaces. Dominating ensemble effect and chirality transfer from the substrate to reaction products are observed, revealing the potential of PdGa as an asymmetric heterogeneous catalyst. Mechanistic insight into enantioselective reactions at chiral surfaces is challenging but crucial for understanding catalytic activity differences observed on Pd-1- and Pd-3-terminated PdGa{111} surfaces.
COMMUNICATIONS CHEMISTRY
(2021)
Article
Chemistry, Physical
Ge Yang, Yali Xie, Yaru Wang, Ying Tang, Leng Leng Chng, Fuyi Jiang, Fanglin Du, Xianfeng Zhou, Jackie Y. Ying, Xun Yuan
Summary: This paper reports on the design of a novel Cu-based nanocatalyst, watersoluble thiolated Cu-30 nanoclusters (NCs), for living cell labeling via CuAAC. The Cu-30 NCs exhibit good biocompatibility, excellent stability, and scalable synthesis, making them a promising catalyst for potential commercial applications. Furthermore, the Cu-30 NCs demonstrate superior catalytic activities for a series of Huisgen cycloaddition reactions with good recyclability, making them suitable for intracellular bioorthogonal applications.
Article
Nanoscience & Nanotechnology
Esther van Andel, Mark Roosjen, Stef van der Zanden, Stefanie C. Lange, Doll Weijers, Maarten M. J. Smulders, Huub F. J. Savelkoul, Han Zuilhof, Edwin J. Tijhaar
Summary: Immunoprecipitation followed by mass spectrometry (IP-MS) is a common method to study protein complexes, but it can be challenging to differentiate true protein interactors from contaminants. This study presents a method for preparing antifouling beads and demonstrates their application in identifying relevant protein-protein interactions with reduced nonspecific protein binding compared to commercial beads.
ACS APPLIED MATERIALS & INTERFACES
(2022)
Article
Chemistry, Multidisciplinary
Yang Chao, Tushar Ulhas Thikekar, Wangjian Fang, Rong Chang, Jiong Xu, Nianfeng Ouyang, Jun Xu, Yan Gao, Minjie Guo, Han Zuilhof, Andrew C-H Sue
Summary: A rim-differentiated pillar[6]arene (RD-P[6]) was successfully synthesized and its solid-state conformation can switch upon guest inclusion. It can not only host metal-containing molecules inside its cavity but also form adducts with other molecules. The development of synthetic strategies to desymmetrize pillararenes offers new opportunities for engineering complex molecular architectures and organic electronic materials.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Alyssa F. J. van den Boom, Han Zuilhof
Summary: In this study, we successfully synthesized a wide range of sulfonamides at room temperature using 4-nitrophenyl benzylsulfonate as a starting material. We achieved yields and reaction times that were comparable to or better than previous reports, demonstrating the viability of sulfur-phenolate exchange as an alternative synthesis method.
Article
Chemistry, Multidisciplinary
Johannes A. M. Damen, Jorge Escorihuela, Han Zuilhof, Floris L. van Delft, Bauke Albada
Summary: The rates of reaction between strained cycloalkynes and cycloalkenes with 1,2-quinone were studied using stopped flow UV-Vis spectroscopy and computational analysis. The results showed that strained alkyne BCN OH 3 reacted over 150 times faster than strained alkene TCO-OH 5, and the introduction of a carbamate derivative reduced the rate constant by almost half. Additionally, the 8-membered strained alkyne BCN OH 3 reacted 16 times faster than the more strained 7-membered THS 2. Thermodynamic activation parameters were determined using the linearized Eyring equation, providing valuable insights into these rapid click reactions.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Correction
Chemistry, Physical
Alyssa F. J. van den Boom, Silvia Ferro, Maria C. Gelvez-Rueda, Han Zuilhof, Bruno Ehrler
JOURNAL OF PHYSICAL CHEMISTRY LETTERS
(2023)
Article
Chemistry, Physical
Alyssa F. J. van den Boom, Silvia Ferro, Maria Gelvez-Rueda, Han Zuilhof, Bruno Ehrler
Summary: In order to improve the efficiency of silicon solar cells, a sensitizing layer of singlet-fission material can be used to increase the current generated by high-energy photons and reduce energy losses. A model using Si(111) surfaces and tetracene was constructed, and the effect on energy transfer was limited despite a change in crystal structure and ordering of the tetracene close to the seed layer, indicating a need for further investigation.
JOURNAL OF PHYSICAL CHEMISTRY LETTERS
(2023)
Article
Chemistry, Multidisciplinary
Lucas W. Teunissen, Maarten M. J. Smulders, Han Zuilhof
Summary: The ability to tailor polymer brushes to specific substrates has made them a powerful surface modification technique. This study presents a modular and straightforward approach for introducing polymer brushes with desired functionality onto different substrates. The method was successfully applied to modifying gold, silicon oxide, and polyester-coated glass substrates with five different block copolymer brushes. Additionally, this method allows for the synthesis of binary brush coatings by simultaneously grafting two different polymer materials.
Article
Chemistry, Multidisciplinary
Lucas W. Teunissen, Maarten M. J. Smulders, Han Zuilhof
Summary: This paper presents a novel coating approach that can achieve polymer brushes with a thickness of up to 19 nm, overcoming the limitation of traditional coatings. An easy-to-apply poly(dopamine) (PDA) primer layer is optimized and deposited on silicon substrates using different methods. Block copolymers are then attached onto the PDA films using a grafting-to approach. The results show that the conditions of PDA deposition and the PDA film thickness greatly affect the stability and grafting efficiency of the block copolymers, and thick polymer layers can be achieved under optimal conditions.
ADVANCED MATERIALS INTERFACES
(2023)
Article
Chemistry, Multidisciplinary
Annemieke van Dam, Robin van Schendel, Satesh Gangarapu, Han Zuilhof, Maarten M. J. Smulders
Summary: The coordination of Fe2+ ion greatly lowers the activation energy and catalyzes the condensation and transimination reactions of imine. The nature of incoming and exiting amines and the substituents on the para-position of the pincer have no significant effect on the reaction. However, the addition of ethylamine molecules reduces the energy barriers to be compatible with experimental values.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Chuanbao Zheng, Nicolo Alvisi, Robbert Jan de Haas, Zhisen Zhang, Han Zuilhof, Renko de Vries
Summary: We analyzed the modularity of a B-M-E triblock protein designed to self-assemble into antifouling coatings. By choosing different solid-binding peptides as binding domain B and different hydrophilic blocks E, we can modulate the nature of the substrate on which the coatings form and the antifouling properties. The B-M-E proteins can easily adapt to form antifouling coatings on any substrate for which solid-binding peptide sequences are available.
Article
Biochemistry & Molecular Biology
Yumei Zhu, Jorge Escorihuela, Haiying Wang, Andrew C. -H. Sue, Han Zuilhof
Summary: We developed an improved method to synthesize a series of pillar[6]arenes with varying numbers of quinone groups. The strength of host-guest interactions with silver ions depends on the number of quinone groups, with a decrease in electron affinity as the number of quinone groups increases. Furthermore, we found that the macrocycle-Ag(2) complexes exhibit a clear distinction between terminal alkynes and internal alkynes, internal alkenes, and terminal alkenes in terms of binding strength.
Article
Chemistry, Organic
Dong-Dong Liang, Natassa Lional, Bas Scheepmaker, Muthusamy Subramaniam, Guanna Li, Fedor M. Miloserdov, Han Zuilhof
Summary: Reaction of sulfonimidoyl fluorides with anilines and Ca(NTf2)(2) leads to the formation of chiral sulfonimidamides by inversion of the stereocenter at a sulfur atom. Enantiospecificity is observed for all non-heterocyclic anilines studied. Combined experimental and computational mechanistic studies demonstrate the chelate-type coordination of the sulfonimidoyl group to Ca(NTf2)(2) and the formation of an S(N)2-like transition state, with the leaving F- ion coordinated to the Ca2+ ion.
Article
Chemistry, Physical
Raghavendra Meena, Johannes Hendrik Bitter, Han Zuilhof, Guanna Li
Summary: This study comprehensively investigates the reaction mechanism of butyric acid hydrodeoxygenation on molybdenum carbide through density functional theory and microkinetic modeling. Heteroatom-doped Mo2C catalysts, particularly Zr and Nb, exhibit enhanced catalytic activity. Linear-scaling relationships between electronic and geometrical descriptors and catalytic performance are established, indicating the crucial roles of dopants' d-band filling and atomic radius. This fundamental understanding provides practical strategies for the design of improved Mo2C-based catalysts for hydrodeoxygenation reactions.
Article
Multidisciplinary Sciences
Joshua A. Homer, Long Xu, Namitharan Kayambu, Qinheng Zheng, Eun Joung Choi, Byeong Moon Kim, K. Barry Sharpless, Han Zuilhof, Jiajia Dong, John E. Moses
Summary: SuFEx is a click reaction for rapid synthesis and discovery of functional molecules. This Primer discusses the essential elements of SuFEx operation, catalysis, and SuFExable connective hubs, as well as explores its applications in drug development, polymer science, and biochemistry. It also examines the potential limitations and promising prospects of this versatile click reaction.
NATURE REVIEWS METHODS PRIMERS
(2023)
Article
Polymer Science
Andriy R. Kuzmyn, Martijn van Galen, Barend van Lagen, Han Zuilhof
Summary: Surface-initiated photoinduced electron transfer-reversible addition-fragmentation chain transfer (SI-PET-RAFT) provides a light-dependent tool for synthesizing polymer brushes on different surfaces. Improved control over SI-PET-RAFT polymerizations under continuous flow conditions allows for prolonged linear growth of the polymer brush and the construction of diblock polymer brushes. The correlation between the molecular weight and dry thickness of the polymer brush is demonstrated using ellipsometry and single-molecule force spectroscopy.
