ArticleChemistry (Weinheim an der Bergstrasse, Germany)2014
Synthesis and transformations of 5-chloro-2,2'-dipyrrins and their boron complexes, 8-chloro-BODIPYs.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2014. 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, 53 citations in OpenAlex.
- Carborane-based BODIPY dyes: synthesis, structural analysis, photophysics and applications.Frontiers in chemistry · 2024Review
- Modulating the Optical Properties of BODIPY Dyes by Noncovalent Dimerization within a Flexible Coordination Cage.Journal of the American Chemical Society · 2020Article
- Stability of a Series of BODIPYs in Acidic Conditions: An Experimental and Computational Study into the Role of the Substituents at Boron.ACS omega · 2018Article
- Further investigation on the nitration of BODIPY with cupric nitrate: crystal structures of 4,4-di-fluoro-1,3,5,7,8-penta-methyl-2-nitro-4-bora-3a,4a-di-aza-Acta crystallographica. Section E, Crystallographic communications · 2018Article
- 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
- Synthesis and properties of a series of carboranyl-BODIPYs.Journal of organometallic chemistry · 2015Article
- 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
- Functionalization of 3,5,8-trichlorinated BODIPY dyes.The Journal of organic chemistry · 2014Article
- 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 at 1 institution in 1 country.
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Abstract
Symmetric dipyrrylketones 1 a,b were synthesized in two steps from the corresponding α-free pyrroles, by reaction with thiophosgene followed by oxidative hydrolysis under basic conditions. The dipyrrylketones produced the corresponding 5-chloro-dipyrrinium salts or 5-ethoxy-dipyrrins on reaction with phosgene or Meerwein's salt, respectively. Boron complexation of the dipyrrins afforded the corresponding 8-functionalized BODIPYs (borondipyrromethenes) in high yields. The 5-chloro-dipyrrinium salts reacted with methoxide or ethoxide ions to produce monopyrrole esters, presumably via a 5,5-dialkoxy-dipyrromethane intermediate. In contrast, 8-chloro-BODIPYs underwent a variety of nucleophilic substitutions of the chloro group in the presence of alkoxide ions, Grignard reagents, and thiols. In the presence of excess alkoxide or Grignard reagent, at room temperature or above, substitution at the boron center also occurred. The 8-chloro-BODIPY was a particularly useful reagent for the preparation of 8-aryl-, 8-alkyl-, and 8-vinyl-substituted BODIPYs in very high yields, using Pd(0) -catalyzed Stille cross-coupling reactions. The X-ray structures of eleven BODIPYs and two pyrroles are presented, and the spectroscopic properties of the synthesized BODIPYs are discussed.
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