ArticleThe Journal of organic chemistry2015
Stepwise Polychlorination of 8-Chloro-BODIPY and Regioselective Functionalization of 2,3,5,6,8-Pentachloro-BODIPY.
Article in The Journal of organic chemistry, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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Who cites it
12 citing papers in PubMed, 64 citations in OpenAlex.
- Regioselective Halogenation of BOPPY Fluorophores and Subsequent Diversification via Cross-Coupling and Aromatic Nucleophilic Substitution Strategies.The Journal of organic chemistry · 2026Article
- Effects of Nitro-Substitution on the Spectroscopic and Self-Assembly Properties of BODIPY Dyes.ACS omega · 2025Article
- Synthesis and Regioselective Functionalization of Tetrafluorobenzo-[α]-Fused BOPYPY Dyes.Inorganic chemistry · 2024Article
- Article
- Oxidative C-H/C-H Coupling of Dipyrromethanes with Azines by TiOMolecules (Basel, Switzerland) · 2021Article
- Structure Based Modulation of Electron Dynamics in meso-(4-Pyridyl)-BODIPYs: A Computational and Synthetic Approach.The journal of physical chemistry. A · 2018Article
- Tetrafluorobenzo-Fused BODIPY: A Platform for Regioselective Synthesis of BODIPY Dye Derivatives.The Journal of organic chemistry · 2018Article
- Synthesis of BODIPY-Peptide Conjugates for Fluorescence Labeling of EGFR Overexpressing Cells.Bioconjugate chemistry · 2017Article
- Enhanced Hypsochromic Shifts, Quantum Yield, and π-π Interactions in a meso,β-Heteroaryl-Fused BODIPY.The Journal of organic chemistry · 2017Article
- Synthesis and Spectroscopic Investigation of a Series of Push-Pull Boron Dipyrromethenes (BODIPYs).The Journal of organic chemistry · 2017Article
- Synthesis and regioselective functionalization of perhalogenated BODIPYs.Organic & biomolecular chemistry · 2016Article
- Synthesis and spectroscopic properties of β,β'-dibenzo-3,5,8-triaryl-BODIPYs.New journal of chemistry = Nouveau journal de chimieArticle
Corrections and comments
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Authors and funding
5 authors at 1 institution in 1 country.
Funding
Abstract
An effective, stepwise methodology for polychlorination of BODIPY using trichloroisocyanuric acid (TCCA) in acetic acid was developed. In this way, selectively substituted di-, tri-, tetra-, and pentachloro-BODIPYs 2-5 were prepared. The pentachloro-BODIPY is shown to undergo regioselective Pd(0)-catalyzed Stille and Suzuki coupling reactions, first at the 8-position followed by the 3,5- and then the 2,6-positions; nucleophilic substitution reactions occur first at the 8- followed by the 3,5-positions, while the 2,6 are unreactive.
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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.