ArticleChemistry (Weinheim an der Bergstrasse, Germany)2015
Synthesis of 3,8-dichloro-6-ethyl-1,2,5,7-tetramethyl-BODIPY from an asymmetric dipyrroketone and reactivity studies at the 3,5,8-positions.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 14 papers.
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Who cites it
14 citing papers in PubMed.
- Crystal structure and Hirshfeld surface analysis of 10-(3-benzyl-thio-phen-2-yl)-5,5-di-fluoro-5Acta crystallographica. Section E, Crystallographic communications · 2026Article
- Regioselective Halogenation of BOPPY Fluorophores and Subsequent Diversification via Cross-Coupling and Aromatic Nucleophilic Substitution Strategies.The Journal of organic chemistry · 2026Article
- Crystal structure and Hirshfeld surface analysis of 5,5-di-fluoro-10-[5-(tri-methyl-sil-yl)furan-2-yl]-5Acta crystallographica. Section E, Crystallographic communications · 2025Article
- Carborane-based BODIPY dyes: synthesis, structural analysis, photophysics and applications.Frontiers in chemistry · 2024Review
- Article
- Tetrafluorobenzo-Fused BODIPY: A Platform for Regioselective Synthesis of BODIPY Dye Derivatives.The Journal of organic chemistry · 2018Article
- Modulation of the Photophysical Properties of β-substituted BODIPY Dyes.Journal of fluorescence · 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 in Vitro Studies of a Series of Carborane-Containing Boron Dipyrromethenes (BODIPYs).Journal of medicinal chemistry · 2016Article
- Stepwise Polychlorination of 8-Chloro-BODIPY and Regioselective Functionalization of 2,3,5,6,8-Pentachloro-BODIPY.The Journal of organic chemistry · 2015Article
- Synthesis and spectroscopic properties of β,β'-dibenzo-3,5,8-triaryl-BODIPYs.New journal of chemistry = Nouveau journal de chimieArticle
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4 authors.
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Abstract
The asymmetric BODIPY 1 a (BODIPY=4,4-difluoro-4-bora-3a,4a-diaza-s-indacene), containing two chloro substituents at the 3,8-positions and a reactive 5-methyl group, was synthesized from the asymmetric dipyrroketone 3, which was readily obtained from available pyrrole 2 a. The reactivity of 3,8-dichloro-6-ethyl-1,2,5,7-tetramethyl-BODIPY 1 a was investigated by using four types of reactions. This versatile BODIPY undergoes regioselective Pd(0) -catalyzed Stille coupling reactions and/or regioselective nucleophilic addition/elimination reactions, first at the 8-chloro and then at the 3-chloro group, using a variety of organostannanes and N-, O-, and S-centered nucleophiles. On the other hand, the more reactive 5-methyl group undergoes regioselective Knoevenagel condensation with an aryl aldehyde to produce a monostyryl-BODIPY, and oxidation with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) gives the corresponding 5-formyl-BODIPY. Investigation of the reactivity of asymmetric BODIPY 1 a led to the preparation of a variety of functionalized BODIPYs with λmax of absorption and emission in the ranges 487-587 and 521-617 nm, respectively. The longest absorbing/emitting compound was the monostyryl-BODIPY 16, and the largest Stokes shift (49 nm) and fluorescence quantum yield (0.94) were measured for 5-thienyl-8-phenoxy-BODIPY 15. The structural properties (including 16 X-ray structures) of the new series of BODIPYs were investigated.
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