Bis-triazolyl BODIPYs: a simple dye with strong red-light emission

Guérin, Charles; Jean‐Gérard, Ludivine; Octobre, Guillaume; Pascal, Simon; Maury, Olivier; Pilet, Guillaume; Ledoux, Audrey; Andrioletti, Bruno

doi:10.1039/c5ra14309h

Cited by 10 publications

(8 citation statements)

References 27 publications

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“…The neutral ligand was synthesized according to the procedure previously described by one of the authors ( Scheme 1 ) [ 14 ].…”

Section: Resultsmentioning

confidence: 99%

“…The neutral ligand was synthesized according to the procedure previously described by one of the authors (Scheme 1) [14]. The mono-alkylated triazolium was prepared by the addition of methyl iodide, while the bis-triazolium was synthesized using the Meerwein's salt (Scheme 2) [18].…”

Section: Resultsmentioning

confidence: 99%

“…During the course of our recent studies on the development of triazole-appended dipyrromethenes (TADs) as powerful fluorescent dyes [ 14 ], we developed the synthesis of a dipyrromethene decorated with coordinating triazole heterocycles. Indeed, thanks to the presence of the three nitrogen atoms of the triazole moiety, the C5-H proton becomes acidic and prone to be involved in hydrogen-bonding with anions [ 15 ].…”

Section: Introductionmentioning

confidence: 99%

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Strong Affinity of Triazolium-Appended Dipyrromethenes (TADs) for BF4−

et al. 2020

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Because BF4− is a labile, non- or weakly coordinating anion, it is generally chosen by chemists who do not want the anion to interfere with the associated cation. Herein, we demonstrate that BF4− actually strongly binds to triazole-appended dipyrromethenes (TADs). In particular, HETCOR NMR experiments and DFT calculations were used to rationalize the results observed with anion titrations. Hence, special care should be taken when considering that BF4− is innocent.

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“…The neutral ligand was synthesized according to the procedure previously described by one of the authors ( Scheme 1 ) [ 14 ].…”

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Strong Affinity of Triazolium-Appended Dipyrromethenes (TADs) for BF4−

et al. 2020

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“…In particular, we have shown that the TAD‐N 4 ‐derived BODIPYs present excellent optical properties, both in organic and in aqueous solution. [ 24 ] In addition, Zn‐ TAD‐N 4 ‐metallocomplexes have recently been proven efficient as catalyst for the carbonation of epoxides. [ 25 ] In parallel, the corresponding triazolium salt TAD‐N 3 C‐H has shown good promises in anion recognition, particularly with BF 4 – .…”

Section: Figurementioning

confidence: 99%

“…The TAD‐N 4 ligand was synthesized in three steps from 2‐dibromoethene‐ N ‐tosylpyrrole 1 according to the methodology developed in our group (Scheme 1). [ 24 ] After a Corey–Fuchs reaction followed by a Huisgen cycloaddition, compound 2 was isolated in 66 % yield. Next, the nitrogen atom deprotection afforded the “half” ligand 3 in 88 % yield.…”

Section: Figurementioning

confidence: 99%

Dipyrromethene‐Triazolylidene Silver Complexes: Synthesis, Structure and Opportunities

et al. 2020

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The synthesis and characterization of unusual silver triazolylidene-containing dipyrromethene complexes are described. The carbene TAD-N 3 C-H obtained from its parent Triazole-Appended Dipyrromethene (TAD-N 4) is an excellent ligand for the complexation of silver, thanks to the proximity between the dipyrromethene scaffold and the triazolylidene. The effect of silver salt stoichiometry on the structure of the complexes was clearly evidenced by 1 H-NMR spectroscopy and Dipyrromethenes (DPM) have been studied in the literature. [1] They constitute key building blocks in the synthesis of pyrrolic macrocycles. [2] Also, their BF 2-complexes (BODIPYs) are well-known for their remarkable optical properties. [3] DPMs present a strong affinity for a large variety of metals, and can be functionalized to afford metallocomplexes displaying original structures with applications in catalysis, [4-8] luminescence [9,10] or in the construction of supramolecular assemblies. [11-13] Most commonly, phosphine [14-16] and carbene [17-21] ligands are used to synthesize silver complexes. In particular, they play a key role in transmetalation reactions. Unexpectedly, to the best of our knowledge, there is only one example of DPM-Ag complex, obtained by addition of a base and (Ph 3 P)AgOTf on an azadipyrromethene solution. [22] In these conditions, a trigonal complex is isolated. Generally, the silver atom interacts with pyrrole double bonds through π interactions. [23] For several years, our group has been involved in the synthesis and the study of a family of functionalized dipyrromethenes, the Triazole-Appended Dipyrromethenes (TADs) (Figure 1). In particular, we have shown that the TAD-N 4-derived BODIPYs present excellent optical properties, both in organic and in aqueous solution. [24] In addition, Zn-TAD-N 4-metallocomplexes [a] A

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Enhanced Penta(organo)[60]fullerenes by Electroactive Donor Units for Supramolecular Polymers

et al. 2018

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New penta(organo)fullerene donor–acceptor systems bearing five recognition units have been prepared in order to promote their self‐assembly in solution and in the solid state. The host cavity formed due to the perfect organization of electro‐ and/or photoactive substituents around the fullerene, together with π–π and electronic interactions, leads to a supramolecular arrangement similar to shuttlecocks nested inside each other.

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Bis-triazolyl BODIPYs: a simple dye with strong red-light emission

Abstract: International audienc

Cited by 10 publications

References 27 publications

Strong Affinity of Triazolium-Appended Dipyrromethenes (TADs) for BF4−

Strong Affinity of Triazolium-Appended Dipyrromethenes (TADs) for BF4−

Dipyrromethene‐Triazolylidene Silver Complexes: Synthesis, Structure and Opportunities

Enhanced Penta(organo)[60]fullerenes by Electroactive Donor Units for Supramolecular Polymers

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