Immobilization of Ir(I) complex on covalent triazine frameworks for C H borylation reactions: A combined experimental and computational study

Tahir, Norini; Muniz‐Miranda, Francesco; Everaert, Jonas; Tack, Pieter; Heugebaert, Thomas S. A.; Leus, Karen; Vincze, László; Stevens, Christian V.; Speybroeck, Véronique Van; Voort, Pascal Van Der

doi:10.1016/j.jcat.2019.01.030

Cited by 44 publications

(39 citation statements)

References 46 publications

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“…[90,58] In principle, a large variety of ligands can be used, creating a versatile platform to engineer supports for anchoring various active complexes. For the CTFtype materials, several N-heterocyclic systems have been synthesized, including (bi)pyridine, [65,40,39,66,82,44,4,68,32] luditine [39] and pyrimidine [39] systems. We recently studied the anchoring of a Ru 2 + , octahedrally chelated by three bidentate polypyridyl ligands, on a biphenyl-based CTF where some of the biphenyl linkers are replaced with polypyridyl ones.…”

Section: Introductionmentioning

confidence: 99%

“…We recently studied the anchoring of a Ru 2 + , octahedrally chelated by three bidentate polypyridyl ligands, on a biphenyl-based CTF where some of the biphenyl linkers are replaced with polypyridyl ones. [58,90] Furthermore, the anchoring of Ir(I) on a CTF containing bipyridine has been shown to be very promising for CÀ H borylation [82] and the postmetalated hexaazatrinaphthylene based CTF with a Cu(OAc) 2 complex can be utilized as an efficient heterogeneous catalyst for the Henry reaction. [83] A review on this topic can be found in Ref.…”

Section: Introductionmentioning

confidence: 99%

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Structural and Photophysical Properties of Various Polypyridyl Ligands: A Combined Experimental and Computational Study

et al. 2020

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Covalent triazine frameworks (CTFs) with polypyridyl ligands are very promising supports to anchor photocatalytic complexes. Herein, we investigate the photophysical properties of a series of ligands which vary by the extent of the aromatic system, the nitrogen content and their topologies to aid in selecting interesting building blocks for CTFs. Interestingly, some linkers have a rotational degree of freedom, allowing both a trans and cis structure, where only the latter allows anchoring. Therefore, the influence of the dihedral angle on the UV-Vis spectrum is studied. The photophysical properties are investigated by a combined computational and experimental study. Theoretically, both static and molecular dynamics simulations are performed to deduce ground-and excited state properties based on density functional theory (DFT) and time-dependent DFT. The position of the main absorption peak shifts towards higher wavelengths for an increased size of the π-system and a higher π-electron deficiency. We found that the position of the main absorption peak among the different ligands studied in this work can amount to 271 nm; which has a significant impact on the photophysical properties of the ligands. This broad range of shifts allows modulation of the electronic structure by varying the ligands and may help in a rational design of efficient photocatalysts.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Structural and Photophysical Properties of Various Polypyridyl Ligands: A Combined Experimental and Computational Study

et al. 2020

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“…Very recently, our group reported the post-functionalization of bpyCTF with (Ir(OMe)(cod)) 2 complex towards the development of a highly stable and efficient catalyst for the CH borylation of aromatic compounds (Figure 7) [52]. The synthesized Ir(I)@bpyCTF catalyst exhibited excellent catalytic activity for CH borylation of arenes and heteroarenes in the presence of B 2 Pin 2 as a boron source.…”

Section: Ctfs As Support For Heterogeneous Catalysismentioning

confidence: 99%

“…Structural representation of the Ir(I)@bpyCTF catalyzed CH boryation of aromatic compound in the presence of B 2 Pin 2 as a boron source (reproduced with permission from [52]. Copyright 2019, Elsevier).…”

Section: Figures Schemes and Tablementioning

confidence: 99%

Development of Covalent Triazine Frameworks as Heterogeneous Catalytic Supports

et al. 2019

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Covalent triazine frameworks (CTFs) are established as an emerging class of porous organic polymers with remarkable features such as large surface area and permanent porosity, high thermal and chemical stability, and convenient functionalization that promotes great potential in heterogeneous catalysis. In this article, we systematically present the structural design of CTFs as a versatile scaffold to develop heterogeneous catalysts for a variety of chemical reactions. We mainly focus on the functionalization of CTFs, including their use for incorporating and stabilization of nanoparticles and immobilization of molecular complexes onto the frameworks.

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“…Similarly, Inagaki developed the heterogeneous catalyst Ir-bpy-PMO ( S12-2 ), which in combination with the inexpensive boron source HBpin facilitated the C−H borylation of aromatic and heteroaromatic compounds, while the catalytic activity of Ir-bpy-PMO was comparable to that of homogenous catalytic systems (Scheme 12) [75]. Another example of a heterogeneous catalyst for C−H borylation reactions is based on the covalent triazine framework (CTF) prepared by Van Der Voort et al They developed a bipyridine-based CTF and then metalated it with the Ir(I) complex so as to prepare an air-stable catalyst ( S12-3 ) for the C−H borylation of various aromatic compounds, including indole [76]. The borylation reactions proceeded in non-polar solvent under mild reaction conditions, and the catalyst could be recycled at least five times with only a small decrease in activity (Scheme 12).…”

Section: Synthetic Approaches To Indolylboronic Acidsmentioning

confidence: 99%

Indolylboronic Acids: Preparation and Applications

et al. 2019

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Indole derivatives are associated with a variety of both biological activities and applications in the field of material chemistry. A number of different strategies for synthesizing substituted indoles by means of the reactions of indolylboronic acids with electrophilic compounds are considered the methods of choice for modifying indoles because indolylboronic acids are easily available, stable, non-toxic and new reactions using indolylboronic acids have been described in the literature. Thus, the aim of this review is to summarize the methods available for the preparation of indolylboronic acids as well as their chemical transformations. The review covers the period 2010–2019.

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Immobilization of Ir(I) complex on covalent triazine frameworks for C H borylation reactions: A combined experimental and computational study

Cited by 44 publications

References 46 publications

Structural and Photophysical Properties of Various Polypyridyl Ligands: A Combined Experimental and Computational Study

Structural and Photophysical Properties of Various Polypyridyl Ligands: A Combined Experimental and Computational Study

Development of Covalent Triazine Frameworks as Heterogeneous Catalytic Supports

Indolylboronic Acids: Preparation and Applications

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