381218-96-8

Basic information

• Product Name: Boronic acid, (4-[2,2':6',2''-terpyridin]-4'-ylphenyl)-
• CAS NO: 381218-96-8
• Molecular Formula: C21H16BN3O2
• Molecular Weight: 353.188
• Mol File: 381218-96-8.mol

Chemical Properties

• CAS DataBase Reference: Boronic acid, (4-[2,2':6',2''-terpyridin]-4'-ylphenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Boronic acid, (4-[2,2':6',2''-terpyridin]-4'-ylphenyl)-(381218-96-8)
• EPA Substance Registry System: Boronic acid, (4-[2,2':6',2''-terpyridin]-4'-ylphenyl)-(381218-96-8)

Safety Data

• Hazardous Substances Data: 381218-96-8(Hazardous Substances Data)

Upstream product

• 1122-62-9 2-acetylpyridine 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 87199-17-5 4-formylphenylboronic acid, 
• 10602-01-4 p-bromobenzaldehyde 1,3-dioxolane 
• 1122-91-4 4-bromo-benzaldehyde 
• 89972-76-9 4'-(4-bromo-phenyl)-[2,2';6',2'']terpyridine 
• 381218-92-4 4'-[4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl]-2,2':6',2''-terpyridine 

Downstream Products

• 1219501-45-7 4-(7,8,13,14-tetrahydroquino[8,7-k][1,8]phenanthrolin-6-yl)-4'([2,2';6',2'']terpyridin-4'-yl)biphenyl 
• 1219501-43-5 4-(5,6,8,9-tetrahydroquino[8,7-b][1,10]phenanthrolin-7-yl)-4'([2,2';6',2'']terpyridin-4'-yl)biphenyl 
• 1374792-56-9 3,4-bis(4'-terpyridyl-p-phenyl)-o-dicarbomethoxybenzene 
• 1401254-36-1 1,2-bis(benzyloxy)-4,5-bis[p-(4′-terpyridinyl)phenyl]benzene 
• 1431790-35-0 2,4-bis(4'-terpyridyl-p-phenyl)-1,5-dimethoxybenzene 

Relevant articles and documents

Photocatalytic atom transfer radical addition to olefins utilizing novel photocatalysts

Photocatalysis is a rapidly evolving area of research in modern organic synthesis. Among the traditional photocatalysts, metal-complexes based on ruthenium or iridium are the most common. Herein, we present the synthesis of two photoactive, ruthenium-based complexes bearing pyridine-quinoline or terpyridine ligands with extended aromatic conjugation. Our complexes were utilized in the atom transfer radical addition (ATRA) of haloalkanes to olefins, using bromoacetonitrile or bromotrichloromethane as the source of the alkyl group. The tailor-made ruthenium-based catalyst bearing the pyridine-quinoline bidentate ligand proved to be the best-performing photocatalyst, among a range of metal complexes and organocatalysts, efficiently catalyzing both reactions. These photocatalytic atom transfer protocols can be expanded into a broad scope of olefins. In both protocols, the photocatalytic reactions led to products in good to excellent isolated yields.

Supersnowflakes: Stepwise Self-Assembly and Dynamic Exchange of Rhombus Star-Shaped Supramolecules

With the goal of increasing the complexity of metallo-supramolecules, two rhombus star-shaped supramolecular architectures, namely, supersnowflakes, were designed and assembled using multiple 2,2′:6′,2″-terpyridine (tpy) ligands in a stepwise manner. In the design of multicomponent self-assembly, ditopic and tritopic ligands were bridged through Ru(II) with strong coordination to form metal-organic ligands for the subsequent self-assembly with a hexatopic ligand and Zn(II). The combination of Ru(II)-organic ligands with high stability and Zn(II) ions with weak coordination played a key role in the self-assembly of giant heteroleptic supersnowflakes, which encompassed three types of tpy-based organic ligands and two metal ions. With such a stepwise strategy, the self-sorting of individual building blocks was prevented from forming the undesired assemblies, e.g., small macrocycles and coordination polymers. Furthermore, the intra- and intermolecular dynamic exchange study of two supersnowflakes by NMR and mass spectrometry revealed the remarkable stability of these giant supramolecular complexes.

Detection of Picric Acid by Terpy-Based Metallo-Supramolecular Fluorescent Coordination Polymers in Aqueous Media

The synthesis of two linear terpy-based metallo-supramolecular fluorescent coordination polymers through 1∶1 complexation of Zn2+ and Cd2+ ions with ditopic terpyridine ligand was reported. The dispersibility of P1 and P2 was significantly improved in organic solvent and water through the introduction of hydrophilic oligo-ethyoxy side chain. Two polymers displayed yellow light emission both in solution and the solid state due to the intra-ligand charge transfer (ILCT) between the d10 metal ions and the conjugated spacer unit. These coordination polymers were explored as fluorescent chemosensors for detecting picric acid in aqueous media, displaying high sensitivity and good selectivity. In addition, test strips were prepared from these polymers and exhibited the practical potential of detecting the NACs pollutants in the outdoor water for public safety and security.

Constructing High-Generation Sierpiński Triangles by Molecular Puzzling

Three generations of metalated trigonal supramolecular architectures, so-called metallo-triangles, were assembled from terpyridine (tpy) complexes. The first generation (G1) metallo-triangles were directly obtained by reacting a bis(terpyridinyl) ligand with a 60° bite angle and ZnII ions. The direct self-assembly of G2 and G3 triangles by mixing organic ligands and ZnII, however, only generated a mixture of G1 and G2, as well as a trace amount of insoluble polymer-like precipitate. Therefore, a modular strategy based on the connectivity of ?tpy?Ru2+?tpy? was employed to construct two metallo-organic ligands for the assembly of G2 and G3 Sierpiński triangles. The metallo-organic ligands LA and LB with multiple free terpyridines were obtained through Suzuki cross-coupling of the RuII complexes, and then assembled with ZnII or CdII to obtain high-generation metallo-triangular architectures in nearly quantitative yield. The G1–G3 architectures were characterized by NOESY and DOSY NMR spectroscopy, ESI-MS, TWIM-MS, and transmission electron microscopy.

Tunable Luminescent Lanthanide Supramolecular Assembly Based on Photoreaction of Anthracene

Lanthanide luminescence materials generally show great superiority in light-emitting materials, gaining increasingly exploration in the design of advanced functional materials. Herein, we prepared a supramolecular assembly via the coordination of a host m

Core substituted naphthalene diimide-metallo bisterpyridine supramolecular polymers: Synthesis, photophysics and morphology

A series of metallo Ru(ii), Fe(ii), Co(ii) bisterpyridine polymers were prepared with naphthalene diimide (NDI) groups inserted between two 4′-phenyl-2,2:6′,2′′-terpyridine (phtpy) groups. Core-substituted NDIs typically have long-lived excited states with relatively high quantum yields, yet the NDI emission in these metallopolymers was completely quenched, most likely because of efficient electron-transfer from the M(phtpy)22+ groups to the excited NDIs. AFM, TEM and SEM experiments indicate that the regiochemistry of the substitution on the core of the naphthalene diimide, together with coordination of the terpyridine ligand to different metals, strongly influences the morphologies of the resulting metallosupramolecular polymers. The morphologies of spin-coated samples of the para-substituted polymers revealed the formation of long, bundled nanorods. Lengths on the order of ～8 μm were observed for the bundle of the longest polymers (5-Ru) by both AFM and TEM microscopy. The morphologies of the meta substituted polymers, on the other hand, exhibited significantly shorter and less well-defined morphologies. This journal is

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Two superaromatic terpyridine ligands (1 and 2) incorporating a corannulene unit at the 4′-position are reported. The optical and metal sensing properties of both ligands were investigated by the naked eye, and UV-vis and fluorescence spectroscopy in this work. In 1, the corannulene motif is directly connected to the 4′-phenylterpyridine domain, while in 2, the corannulene motif and the 4′-phenylterpyridine domain are separated by an acetylene linker. Both 1 and 2 can work as chemosensors for metal ions and display different optical responses to various metal ions. It is shown that both ligands exhibit a colorimetric sensing ability for Fe2+ through an obvious color change from colorless to magenta, and this color change can be observed easily by the naked eye. The addition of Fe2+ also leads to significant changes in the absorption spectra of the ligands. A characteristic red shift in the emission spectra is observed in the presence of Zn 2+, which facilitates the discrimination of Zn2+ from other metal ions. In addition, density functional theory (DFT) and time-dependent-density functional theory (TD-DFT) calculations were performed and shown to be consistent with the observed experimental results. The Royal Society of Chemistry.

Towards molecular construction platforms: Synthesis of a metallotricyclic spirane based on bis(2,2′:6′,2"-terpyridine)RuII connectivity

The design and construction of the first multicomponent stepwise assembly of a II-tpy>-based (tpy=terpyridine), three-dimensional, propeller-shaped trismacrocycle, 8, are reported. Key steps in the synthesis involve the preparation of a

Stoichiometric self-assembly of isomeric, shape-persistent, supramacromolecular bowtie and butterfly structures

Two novel macromolecular constitutional isomers have been self-assembled from previously unreported terpyridine ligands in a three-component system. The terpyridine ligands were synthesized in high yields via a key Suzuki coupling. Restrictions of the pos

Stable, trinuclear Zn(ii)- and Cd(ii)-metallocycles: TWIM-MS, photophysical properties, and nanofiber formation

A series of trimeric, Zn(ii)- and Cd(ii)-metallocycles is reported. Structural characterization of the highly stable triangles was supported by traveling-wave ion mobility-mass spectrometry (TWIM-MS) and gradient tandem mass spectrometry (gMS2). Their unique photophysical properties and self-assembly to form nanofibers are also described.