Efficient Conversion of Inert Nitriles to Multifunctional Poly(5-amino-1,2,3-triazole)s via Regioselective Click Polymerization with Azide Monomers under Ambient Conditions DOI
Jia Wang, Tian Tian,

Rongyuan Zhang

и другие.

Journal of the American Chemical Society, Год журнала: 2024, Номер 146(10), С. 6652 - 6664

Опубликована: Фев. 29, 2024

Nitrile compounds are abundant, stable, cheap, and readily available natural chemical industrial sources. However, the efficient conversion of nitrile monomers to functional polymers is mostly limited due their inert reactivity, developing polymerizations based on under very mild conditions still a big challenge. In this work, facile powerful base-catalyzed acetonitrile-azide click polymerization was successfully established ambient conditions. This also enjoys merits short reaction time (15 min), 100% atom economy, transition-metal-free catalyst system, regioselectivity. A series poly(5-amino-1,2,3-triazole)s (PATAs) with high weight-average molecular weights (Mw, up 204,000) were produced in excellent yields (up 99%). The PATAs containing tetraphenylethene (TPE) moieties exhibit unique aggregation-induced emission (AIE) characteristics, which could be used sensitively detect Fe(III) ions low limit detection (1.205 × 10–7 M) specifically image lysosomes living cells. Notably, facilely post-modified primary amino groups polymer chains even through one-pot tandem reaction. Thus, work not only establishes new convert stable nitriles but generates versatile properties for diverse applications.

Язык: Английский

meso-Methyl BODIPY Photocages: Mechanisms, Photochemical Properties, and Applications DOI
Pradeep Shrestha, Dnyaneshwar Kand, Roy Weinstain

и другие.

Journal of the American Chemical Society, Год журнала: 2023, Номер 145(32), С. 17497 - 17514

Опубликована: Авг. 3, 2023

meso-methyl BODIPY photocages have recently emerged as an exciting new class of photoremovable protecting groups (PPGs) that release leaving upon absorption visible to near-infrared light. In this Perspective, we summarize the development these PPGs and highlight their critical photochemical properties applications. We discuss PPGs, structure–photoreactivity studies, insights into photoreaction mechanism, scope functional can be caged, chemical synthesis structures, how substituents alter water solubility PPG direct specific subcellular compartments. Applications exploit unique optical are also discussed, from wavelength-selective photoactivation biological studies photoresponsive organic materials photomedicine.

Язык: Английский

Процитировано

67
X‐yne click polymerization DOI Creative Commons

Xinyao Fu,

Anjun Qin, Ben Zhong Tang

и другие.

Aggregate, Год журнала: 2023, Номер 4(5)

Опубликована: Май 6, 2023

Abstract Alkyne‐based click polymerizations have been nurtured into a powerful synthetic technique for the preparation of new polymers with advanced structures and versatile properties. Among them, emerging thiol‐yne, hydroxyl‐yne, amino‐yne made remarkable progress from reactions to applications. These avoid usage inherently dangerous monomers are safer operate than classical azide‐alkyne polymerization (AACP), making them more prospective diverse To greatly promote alkyne‐based beyond AACP, concept “X‐yne polymerization” is proposed unify where “X” denotes that can react alkynes under mild reaction conditions, including thiols, alcohols, amines, other promising ones. In this review, we mainly present brief account X‐yne discuss in detail challenges opportunities field.

Язык: Английский

Процитировано

60
Copolymerization Involving Sulfur-Containing Monomers DOI
Tian‐Jun Yue, Wei‐Min Ren, Xiao‐Bing Lu

и другие.

Chemical Reviews, Год журнала: 2023, Номер 123(24), С. 14038 - 14083

Опубликована: Ноя. 2, 2023

Incorporating sulfur (S) atoms into polymer main chains endows these materials with many attractive features, including a high refractive index, mechanical properties, electrochemical and adhesive ability to heavy metal ions. The copolymerization involving S-containing monomers constitutes facile method for effectively constructing polymers diverse structures, readily tunable sequences, topological structures. In this review, we describe the recent advances in synthesis of via or multicomponent polymerization techniques concerning variety monomers, such as dithiols, carbon disulfide, carbonyl sulfide, cyclic thioanhydrides, episulfides elemental (S8). Particularly, significant focus is paid precise control main-chain sequence, stereochemistry, structure achieving high-value applications.

Язык: Английский

Процитировано

49
Metal-Free Click-Chemistry: A Powerful Tool for Fabricating Hydrogels for Biomedical Applications DOI Creative Commons
Aysun Degirmenci, Rana Sanyal,

Amitav Sanyal

и другие.

Bioconjugate Chemistry, Год журнала: 2024, Номер 35(4), С. 433 - 452

Опубликована: Март 22, 2024

Increasing interest in the utilization of hydrogels various areas biomedical sciences ranging from biosensing and drug delivery to tissue engineering has necessitated synthesis these materials using efficient benign chemical transformations. In this regard, advent "click" chemistry revolutionized design a range reactions was utilized obtain with increased control over their physicochemical properties. The ability apply paradigm both synthetic natural polymers as hydrogel precursors further expanded utility network formation. particular, integrate clickable handles at predetermined locations polymeric components enables formation well-defined networks. Although, early years chemistry, copper-catalyzed azide-alkyne cycloaddition widely employed, recent have focused on use metal-free transformations, since residual metal impurities may interfere or compromise biological function such materials. Furthermore, many non-metal-catalyzed transformations enable fabrication injectable hydrogels, well microstructured gels spatial temporal control. This review article summarizes advances highlights applications thus obtained One could envision that versatile would continue revolutionize functional geared address unmet needs sciences.

Язык: Английский

Процитировано

20
Sulfenyl Chlorides: An Alternative Monomer Feedstock from Elemental Sulfur for Polymer Synthesis DOI
Kyung Seok Kang,

Chisom Olikagu,

Taeheon Lee

и другие.

Journal of the American Chemical Society, Год журнала: 2022, Номер 144(50), С. 23044 - 23052

Опубликована: Дек. 7, 2022

A polymerization methodology is reported using sulfur monochloride (S2Cl2) as an alternative feedstock for polymeric materials. S2Cl2 inexpensive petrochemical derived from elemental (S8) but has numerous advantages a reactive monomer vs S8. This new process, termed sulfenyl chloride inverse vulcanization, exploits the high reactivity and miscibility of with broad range allylic monomers to prepare soluble, molar-mass linear polymers, segmented block copolymers, crosslinked thermosets greater synthetic precision than achieved classical vulcanization. step-growth addition also allows preparation class thiol-free, inexpensive, highly optically transparent (α = 0.045 cm–1 at 1310 nm), which exhibit among best optical transparency low birefringence relative commodity while possessing higher refractive index (n > 1.6) in visible near-infrared spectra. The fabrication large-sized components demonstrated.

Язык: Английский

Процитировано

45
Polymerizations of Activated Alkynes DOI
Benzhao He,

Jiachang Huang,

Xinyue Liu

и другие.

Progress in Polymer Science, Год журнала: 2022, Номер 126, С. 101503 - 101503

Опубликована: Янв. 5, 2022

Язык: Английский

Процитировано

42
Click Chemistry: Reaction Rates and Their Suitability for Biomedical Applications DOI Creative Commons
Tracey Luu, Katie Gristwood, James C. Knight

и другие.

Bioconjugate Chemistry, Год журнала: 2024, Номер 35(6), С. 715 - 731

Опубликована: Май 22, 2024

Click chemistry has become a commonly used synthetic method due to the simplicity, efficiency, and high selectivity of this class chemical reactions. Since their initial discovery, further click methods have been identified added toolbox reactions for biomedical applications. However, selecting most suitable reaction specific application is often challenging, as multiple factors must be considered, including selectivity, reactivity, biocompatibility, stability. Thus, review provides an overview benefits limitations well-established with particular focus on importance considering rates, overlooked criterion little available guidance. The understanding each beyond simply speed discussed comprehensively reference recent research which utilized chemistry. This aims provide practical resource researchers guide selection classes different

Язык: Английский

Процитировано

16
Sustainable polymers from renewable resources through click and multicomponent reactions DOI
Serter Luleburgaz, Emrah Çakmakçı, Hakan Durmaz

и другие.

European Polymer Journal, Год журнала: 2024, Номер 209, С. 112897 - 112897

Опубликована: Март 6, 2024

Язык: Английский

Процитировано

15
Silicon-Containing Thiol-Specific Bioconjugating Reagent DOI
Zhenguo Zhang, Lanyang Li,

Hailun Xu

и другие.

Journal of the American Chemical Society, Год журнала: 2024, Номер 146(3), С. 1776 - 1782

Опубликована: Янв. 10, 2024

A new bioconjugation reagent containing silicon has been developed for the selective reaction with thiols. The inclusion of significantly improves chemoselectivity and suppresses retro processes, thereby exceeding capabilities traditional reagents. method is versatile compatible a broad range thiols unsaturated carbonyl compounds yields moderate to high results. These reactions can be conducted under biocompatible conditions, making them suitable protein bioconjugation. resulting conjugates display good stability in presence various biomolecules, which suggests their potential application synthesis antibody–drug conjugates. Furthermore, moiety within conjugated products opens up avenues drug release bridging inorganics other disciplines. This class silicon-containing thiol-specific reagents significant implications researchers working bioanalytical science medicinal chemistry leads innovative opportunities advancing field research chemistry.

Язык: Английский

Процитировано

14
Rapid, Mild Synthesis of Transparent Polyimides with High Refractive Index via Thiol-Michael Click Reaction DOI

Shuyu Xue,

Xingfeng Lei,

Yuyang Xiao

и другие.

ACS Applied Polymer Materials, Год журнала: 2024, Номер 6(4), С. 2315 - 2326

Опубликована: Фев. 13, 2024

Polyimides (PIs) are widely used in microelectronics and advanced optical industries due to their excellent overall properties. However, the efficient mild synthesis of PIs from commercially available raw materials poses great challenges polymer chemistry. Here, a rapid versatile thiol-Michael click reaction between imide-containing bismaleimides (BMI) aromatic dithiol is developed. The structural diversity BMI allows for manipulation thermal properties by molecular design with different substituents or dianhydrides backbone. polymerization good enough so that it can be completed only 1 min at room temperature (25 °C) presence triethylamine, affording high weight stability, tensile strength up 126.7 MPa, desirable solubility processability. With introduced sulfur elements, refractive indices as 1.6601, while ensuring transmittance 85% 400 nm. This thiol-maleimide significantly speeds preparation functional have potential applications devices.

Язык: Английский

Процитировано

10