ArticleThe Journal of organic chemistry2014
Functionalization of 3,5,8-trichlorinated BODIPY dyes.
Article in The Journal of organic chemistry, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 13 papers.
What it found
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
13 citing papers in PubMed.
- Regioselective Halogenation of BOPPY Fluorophores and Subsequent Diversification via Cross-Coupling and Aromatic Nucleophilic Substitution Strategies.The Journal of organic chemistry · 2026Article
- Delving into the Inception of BODIPY Dyes: Paradigms of In Vivo Bioimaging, Chemosensing, and Photodynamic/Photothermal Therapy.Pharmaceuticals (Basel, Switzerland) · 2026Review
- Synthesis and Regioselective Functionalization of Tetrafluorobenzo-[α]-Fused BOPYPY Dyes.Inorganic chemistry · 2024Article
- Two-Photon Absorption Response of Functionalized BODIPY Dyes in Near-IR Region by Tuning Conjugation Length and Meso-Substituents.ACS omega · 2023Article
- Organelle-Targeted BODIPY Photocages: Visible-Light-Mediated Subcellular Photorelease.Angewandte Chemie (International ed. in English) · 2019Article
- 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
- Stepwise Polychlorination of 8-Chloro-BODIPY and Regioselective Functionalization of 2,3,5,6,8-Pentachloro-BODIPY.The Journal of organic chemistry · 2015Article
- 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.Chemistry (Weinheim an der Bergstrasse, Germany) · 2015Article
- 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
4 authors.
Funding
Abstract
Catalytic hydrogenation of dibenzyl 5-dipyrroketone-2,9-dicarboxylates followed by decarboxylative iodination affords a 2,9-diiododipyrroketone which gives a 2,5,9-trichlorodipyrromethene hydrochloride after nucleophilic addition/elimination, with adventitious chloride to replace the two iodide groups. Treatment with BF3·Et2O gives a 3,5,8-trichloro-BODIPY that readily undergoes regioselective Stille coupling at the 8-position, or homo/mixed couplings at the 3,8- or 3,5- and 8-positions. Stepwise and controlled replacement of the 3,5- and 8-chlorine atoms using Stille reagents results in formation of a completely unsymmetrical trisubstituted BODIPY. Several examples of unsymmetrical BODIPYs were synthesized and characterized using this methodology. Structure features of new BODIPYs are discussed within the context of 14 new X-ray structures, and photophysical parameters of all new BODIPY compounds are reported and discussed.
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Registered trials
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.