Carbon-rich “Click” 1,2,3-triazoles: hexaphenylbenzene and hexa-peri-hexabenzocoronene-based ligands for Suzuki–Miyaura catalysts

Wright, J. J.; Crowley, James D.; Lucas, Nigel T.

doi:10.1039/c6cc07413h

Cited by 11 publications

(4 citation statements)

References 63 publications

(27 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…A few other donor‐acceptor systems based on dicyanoetheno‐bridged HBCs were studied for their dimerization, trimerizations, [247] as well as photoisomerization reactions [248] . Moreover, HBC‐1,2,3‐triazole‐palladium complexes served as efficient catalyst in mediating Suzuki‐Miyaura reactions [249] …”

Section: Resultsmentioning

confidence: 99%

Coronenes, Benzocoronenes and Beyond: Modern Aspects of Their Syntheses, Properties, and Applications

Kumar

Tao

2021

Chemistry An Asian Journal

View full text Add to dashboard Cite

In recent years, a variety of new designs of coronene‐based polycyclic aromatic hydrocarbons (PAHs) with diverse functions have emerged to serve as complementary materials in organic chemistry and materials chemistry. In the present review, we highlight the modern aspects of syntheses related to or different from the strategies used in the early era of coronene research. Systematic extension and expansion of coronene backbones to wide categories of angular PAHs are covered. The substitution and extension of coronene architectures, by incorporating functional groups and by fusing small and large conjugated units, advatangeously enrich their photophysical, electrochemical, self‐assembling, and other properties, of which are discussed to demostrate their impact in materials chemistry. While the highly symmetric coronenes, tribenzocoronenes and hexabenzocoronenes conceived wide potential in charge‐transporting, electroluminescent, sensing, and other applications, other related derivatives such as dibenzo, tetrabenzo and pentabenzocoronenes also displayed their potentials as exemplified by their use as charge‐conduction channel in transistor application.

show abstract

Section: Resultsmentioning

confidence: 99%

Coronenes, Benzocoronenes and Beyond: Modern Aspects of Their Syntheses, Properties, and Applications

Kumar

Tao

2021

Chemistry An Asian Journal

View full text Add to dashboard Cite

show abstract

“…A number of metal complexes with ligands bearing an HBC substituent have been reported, ,− along with N -heteroaromatic analogues; − in examples where a crystal structure was obtained, the HBC groups play a leading role in directing the supramolecular structure. Challenges exist in synthesizing HBC ligands, especially those with multiple HBC substituents, as insolubility can result from the extended π-stacking, thus limiting further application.…”

Section: Introductionmentioning

confidence: 99%

Superphenylphosphines: Nanographene-Based Ligands That Control Coordination Geometry and Drive Supramolecular Assembly

2018

Self Cite

View full text Add to dashboard Cite

Tertiary phosphines remain widely utilized in synthesis, most notably as supporting ligands in metal complexes. A series of triarylphosphines bearing one to three hexa-peri-hexabenzocoronene (HBC) substituents has been prepared by an efficient divergent route. These "superphenylphosphines", P{HBC(t-Bu)}Ph (n = 1-3), form the palladium complexes PdClL and PdClL where the isomer distribution in solution is dependent on the number of HBC substituents. The crystalline structures of five complexes all show intramolecular π-stacking between HBC-phosphines to form a supramolecular bidentate-like ligand that distorts the metal coordination geometry. When n = 2 or 3, the additional HBC substituents engage in intermolecular π-stacking to assemble the complexes into continuous ribbons or sheets. The phosphines adopt HBC's characteristics including strong optical absorption, green emission, and redox activity.

show abstract

“…In organic chemistry, biochemistry, and material chemistry, 1,2,3-triazole is frequently used as a flexible building block or synthetic precursor. Recently, the 1,2,3-triazole ligand has demonstrated catalytic efficacy in organic synthesis by allowing its nitrogen lone pair electrons to bind to the metal to form a true catalyst . Additionally, anionic 1,2,3-triazole is a structural isomer of NHC and a stronger π-acceptor that could bind to transition metals, imparting additional catalytic capabilities to metal centers.…”

Section: Introductionmentioning

confidence: 99%

Triazole-phosphine Pd(II)-Enabled Dehydrogenation of Alcohols or Amines: A Combination of Experimental and Theoretical Study

et al. 2022

View full text Add to dashboard Cite

We describe a novel triazole-phosphine Pd(II) (TPP) complex-catalyzed dehydrogenation reaction of alcohols or amines by using iodobenzene as the oxidant, in which a unique butterfly TPP dimer is first prepared via a three-component reaction of 1,2,3-triazole, P(Cy) 3 , and PdCl 2 and the competitive cross-coupling reaction of iodobenzene with alcohols or amines could be avoided under TPP catalysis. In particular, the primary alcohols and imines can be further oxidized into acids or nitriles in a tunable manner, respectively. Preliminary mechanistic results by density functional theory calculation suggest that this reaction follows the Pd(II)−Pd(IV) catalytic pathway and the process of TPP-catalyzed oxidation dehydrogenation of alcohol or amine to form unsaturated bonds and Pd(II)−H species generated before the oxidative addition of TPP with iodobenzene, thereby avoiding competitive cross-coupling.

show abstract

Carbon-rich “Click” 1,2,3-triazoles: hexaphenylbenzene and hexa-peri-hexabenzocoronene-based ligands for Suzuki–Miyaura catalysts

Cited by 11 publications

References 63 publications

Coronenes, Benzocoronenes and Beyond: Modern Aspects of Their Syntheses, Properties, and Applications

Coronenes, Benzocoronenes and Beyond: Modern Aspects of Their Syntheses, Properties, and Applications

Superphenylphosphines: Nanographene-Based Ligands That Control Coordination Geometry and Drive Supramolecular Assembly

Triazole-phosphine Pd(II)-Enabled Dehydrogenation of Alcohols or Amines: A Combination of Experimental and Theoretical Study

Contact Info

Product

Resources

About