Frontispiz: Diversity Oriented Clicking (DOC): Divergent Synthesis of SuFExable Pharmacophores from 2‐Substituted‐Alkynyl‐1‐Sulfonyl Fluoride (SASF) Hubs

Smedley, Christopher J.; Li, Gencheng; Barrow, Andrew S.; Gialelis, Timothy L.; Giel, Marie‐Claire; Ottonello, Alessandra; Cheng, Yunfei; Kitamura, Seiya; Wolan, Dennis W.; Sharpless, K. Barry; Moses, John E.

doi:10.1002/ange.202083063

Cited by 5 publications

(4 citation statements)

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“…As such, the author successfully utilized HPC‐ESF as a highly sensitive turn‐off sensor of trypsin with a detection limit of 11.9 μg/ml in real urine samples [70]. In the same year, the author developed AIE‐active and a SuFEx‐reactive 1,3,4‐triphenyl‐1,4‐dihydro‐1,4‐epoxynaphthalene (ENAP) derivatives through catalyst‐free Diels–Alder reactions between 1,3‐diphenylisobenzofuran as the diene and 2‐substituted‐alkynyl‐1‐sulfonyl fluoride as the dienophile (Figure 4d) [72]. Although the roles of SuFEx‐reactive groups were not clear, these AIEgens were applicable for latent fingerprint detection, fixed cell imaging, and bacteria imaging (Figure 4e) [71].…”

Section: Metal‐free Click Reactionsmentioning

confidence: 99%

Metal‐free click and bioorthogonal reactions of aggregation‐induced emission probes for lighting up living systems

Segawa,

He,

Tang

2023

Luminescence

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In 2002, two transformative research paradigms emerged: ‘click chemistry’ and ‘aggregation‐induced emission (AIE),’ both leaving significant impacts on early 21st‐century academia. Click chemistry, which describes the straightforward and reliable reactions for linking two building blocks, has simplified complex molecular syntheses and functionalization, propelling advancements in polymer, material, and life science. In particular, nontoxic, metal‐free click reactions involving abiotic functional groups have matured into bioorthogonal reactions. These are organic ligations capable of selective and efficient operations even in congested living systems, therefore enabling in vitro to in vivo biomolecular labelling. Concurrently, AIE, a fluorogenic phenomenon of twisted π‐conjugated compounds upon aggregation, has offered profound insight into solid‐state photophysics and promoted the creation of aggregate materials. The inherent fluorogenicity and aggregate‐emission properties of AIE luminogens have found extensive application in biological imaging, characterized by their high‐contrast and photostable fluorescent signals. As such, the convergence of these two domains to yield efficient labelling with excellent fluorescence images is an anticipated progression in recent life science research. In this review, we intend to showcase the synergetic applications of AIE probes and metal‐free click or bioorthogonal reactions, highlighting both the achievements and the unexplored avenues in this promising field.

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Section: Metal‐free Click Reactionsmentioning

confidence: 99%

Metal‐free click and bioorthogonal reactions of aggregation‐induced emission probes for lighting up living systems

Segawa,

He,

Tang

2023

Luminescence

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“…16 17 18 Accordingly, the high demand has brought about the development of a number of new synthetic methods to access these motifs, including approaches via functionalization reactions 19 20 21 22 23 24 25 26 and modular syntheses. 27 28 29…”

Section: Table 1 Optimization Of the Reaction Condition...mentioning

confidence: 99%

Photo-organocatalytic Synthesis of β-Keto Sulfonyl Fluorides via Radical Fluorosulfonylation of Vinyl Acetates

Wang

Liao

et al. 2022

Synlett

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A metal-free synthesis of useful β-keto sulfonyl fluorides has been established via radical fluorosulfonylation of ketone-derived vinyl acetates under photoredox organocatalysis by using 1-fluorosulfonyl benzoimidazolium (FABI) as the fluorosulfonyl radical source and oxygen-doped anthanthrene (ODA) as the photocatalyst. A series of aryl and alkyl β-keto sulfonyl fluorides as well as cyclic analogues can be readily obtained in moderate to high yields from widely available ketone starting materials.

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“…[ 29 ] Molecules containing the valuable S–F bond act as a “ SuFExable molecular plugin ” allowing multiple linkages formed around a central sulfur core, which to date include the connective gases SO 2 F 2 and SOF 4 , [ 28 ] and the carbon‐based connectors ethenesulfonyl fluoride (ESF), [ 30 ] 1‐bromoethene‐1‐sulfonyl fluoride, [ 31 ] and 2‐substituted‐alkynyl‐1‐sulfonylfluorides. [ 32,33 ] Although SuFEx has made considerable contributions across many areas of chemistry, [ 34 ] it has not been used broadly in the ABS approach or in the construction of AIEgens in comparison to other click chemistry reactions and will only be discussed briefly in this review.…”

Section: Introductionmentioning

confidence: 99%

Click chemistry in the design of AIEgens for biosensing and bioimaging

Giel

Hong

2023

Aggregate

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The development of rapid, selective, and sensitive fluorescent sensors is essential for visualizing and quantifying biological molecules and processes in vitro, ex vitro, and in vivo, which is important for not only fundamental biological studies but the accurate diagnosis of diseases. The emerging field of activity‐based sensing (ABS), a sensing method that utilizes molecular reactivity for analyte detection possesses many advantages including high specificity, sensitivity and accuracy. The aggregation caused quenching phenomenon which occurs in most conventional fluorophores results in reduced labeling efficiency of the target analytes and low photobleaching resistance, therefore limiting the applications of the ABS strategy. In contrast, aggregation induced emission (AIE) active luminogens (AIEgens) provide exceptional molecular frameworks for ABS. Of the many reaction classes utilized in the AIEgen ABS approach, click chemistry has become increasing popular. In this review, the sensing concepts of the ABS approach with AIEgens and the principles of click chemistry are discussed, followed by a systematic summary of the application of specific click chemistry reactions in AIEgen ABS protocols for the detection of an array of target analytes. Furthermore, the utility of click chemistry in the construction of AIEgens for bioimaging will also be showcased throughout the review.

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Frontispiz: Diversity Oriented Clicking (DOC): Divergent Synthesis of SuFExable Pharmacophores from 2‐Substituted‐Alkynyl‐1‐Sulfonyl Fluoride (SASF) Hubs

Abstract: Click‐Chemie Ein vereinheitlichter Ansatz für die Click‐Chemie, genannt diversitätorientiertes Clicking, wird von J. E. Moses et al. im Forschungsartikel auf S. 12560 für die Synthese diverser Leitstrukturen eingeführt.

Cited by 5 publications

References 0 publications

Metal‐free click and bioorthogonal reactions of aggregation‐induced emission probes for lighting up living systems

Metal‐free click and bioorthogonal reactions of aggregation‐induced emission probes for lighting up living systems

Photo-organocatalytic Synthesis of β-Keto Sulfonyl Fluorides via Radical Fluorosulfonylation of Vinyl Acetates

Click chemistry in the design of AIEgens for biosensing and bioimaging

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