ArticleACS central science2017
General Synthetic Method for Si-Fluoresceins and Si-Rhodamines.
Article in ACS central science, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 68 papers.
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Who cites it
68 citing papers in PubMed, 186 citations in OpenAlex.
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- Development of silicon-fluorescein-based photolabile protecting groups with enhanced uncaging quantum yield.RSC advances · 2026Article
- Fast, Bright, and Reversible Fluorescent Labeling of Rhodamine-Binding Proteins.Journal of the American Chemical Society · 2026Article
- Single-Molecule Localization Microscopy in the Nucleus with Self-Labelling Tags: Halo, SNAP, and CLIP Tags.Methods in molecular biology (Clifton, N.J.) · 2026Article
- Optimizing multifunctional fluorescent ligands for intracellular labeling.Proceedings of the National Academy of Sciences of the United States of America · 2025Article
- Molecular recording of cellular protein kinase activity with chemical labeling.Nature chemical biology · 2025Article
- Matrix-designed bright near-infrared fluorophores for precision peripheral nerve imaging.Biomaterials · 2025Article
- Thioether editing generally increases the photostability of rhodamine dyes on self-labeling tags.Proceedings of the National Academy of Sciences of the United States of America · 2025Article
- A privileged ER compartment for posttranslational heteromeric assembly of an ion channel.Proceedings of the National Academy of Sciences of the United States of America · 2025Article
- A privileged ER compartment for post-translational heteromeric assembly of an ion channel.bioRxiv : the preprint server for biology · 2025Article
- Singlets-Driven Photoredox Catalysts: Transforming Noncatalytic Red Fluorophores to Efficient Catalysts.JACS Au · 2024Article
- Optimized Properties and Synthesis of Photoactivatable Diazoketorhodamines Facilitate and Enhance High-Throughput Single-Molecule Tracking.The Journal of organic chemistry · 2024Article
- Extended shortwave infrared absorbing antiaromatic fluorenium-indolizine chromophores.Chemical science · 2024Article
- Excited-State Conjugation/De-Conjugation Driven Nonradiative Thermal Deactivation for Developing Fluorogenic Probes to Diagnose Cancers.Chemical & biomedical imaging · 2024Article
- Silicon-RosIndolizine fluorophores with shortwave infrared absorption and emission profiles enable in vivo fluorescence imaging.Nature chemistry · 2024Article
- Synthesis of Thioxanthone 10,10-Dioxides and Sulfone-Fluoresceins via Pd-Catalyzed Sulfonylative Homocoupling.Organic letters · 2024Article
- Mild and scalable synthesis of phosphonorhodamines.Chemical science · 2023Article
- Optimized Red-Absorbing Dyes for Imaging and Sensing.Journal of the American Chemical Society · 2023Article
8 more citing papers are in PubMed but not listed here.
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Authors and funding
4 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The century-old fluoresceins and rhodamines persist as flexible scaffolds for fluorescent and fluorogenic compounds. Extensive exploration of these xanthene dyes has yielded general structure-activity relationships where the development of new probes is limited only by imagination and organic chemistry. In particular, replacement of the xanthene oxygen with silicon has resulted in new red-shifted Si-fluoresceins and Si-rhodamines, whose high brightness and photostability enable advanced imaging experiments. Nevertheless, efforts to tune the chemical and spectral properties of these dyes have been hindered by difficult synthetic routes. Here, we report a general strategy for the efficient preparation of Si-fluoresceins and Si-rhodamines from readily synthesized bis(2-bromophenyl)silane intermediates. These dibromides undergo metal/bromide exchange to give bis-aryllithium or bis(aryl Grignard) intermediates, which can then add to anhydride or ester electrophiles to afford a variety of Si-xanthenes. This strategy enabled efficient (3-5 step) syntheses of known and novel Si-fluoresceins, Si-rhodamines, and related dye structures. In particular, we discovered that previously inaccessible tetrafluorination of the bottom aryl ring of the Si-rhodamines resulted in dyes with improved visible absorbance in solution, and a convenient derivatization through fluoride-thiol substitution. This modular, divergent synthetic method will expand the palette of accessible xanthenoid dyes across the visible spectrum, thereby pushing further the frontiers of biological imaging.
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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.