69506-91-8

Usage

Structure

A benzene ring with two imidazole rings attached at the 1 and 3 positions

Application

Used as a ligand in coordination chemistry

Specific Use

Synthesis of metal-organic frameworks and coordination polymers

Potential

Building block for designing novel materials

Applications

Catalysis, sensing, and drug delivery

Field of Interest

Supramolecular chemistry and materials science

Upstream product

• 288-32-4 1H-imidazole 
• 108-36-1 1,3-dibromobenzene 
• 626-00-6 1,3-Diiodobenzene 

Downstream Products

• 1325231-96-6 1,3-bis(2-iodo-imidazol-1-yl)benzene 

Relevant academic research and scientific papers

Reprint of structural diversity of cobalt(II) coordination compounds involving bent imidazole ligand: A route from 0D dimer to 3D coordination polymer

Mixed ligand approach could be successfully applied to design porous three-dimensional coordination polymers, involving 1,3-bis(imidazol-1-yl)benzene (1,3-bib) as ligand. Five novel Co(II) compounds with different dimensionality have been synthesized. Utilizing only 1,3-bib in the solvothermal reaction with Co(II) salts, only molecular dimer Co2(bib)2Cl4 or 1D polymer Co2(1,3-bib)2(NO3)2 could be synthesized. Copolymerization technique using additional linear dicarboxylates 1,4-benzenedicarboxylate (1,4-bdc) or 2,6- naphthalenedicarboxylate (2,6-ndc) facilitates the formation of 2D layered coordination polymers Co(1,3-bib)(1,4-bdc) and Co(1,3-bib)(2,6-ndc). Utilizing 4,4′-biphenyldicarboxylate (4,4′-bpdc) as a co-linker, a 3D metal-organic framework Co3(1,3-bib)(4,4′-bpdc)3 (DUT-58, DUT-Dresden University of Technology), possessing two interpenetrated uninodal 8-connected frameworks, has been obtained. DUT-58 exhibits a specific surface area of 1208 m2/g and adsorbs 27 mg/g hydrogen (maximum excess value at 30 bar and 77 K), 0.18 g/g n-butane (at 293 K) and 72 mg/g methane (maximum excess value at 60 bar and 298 K).

Silver(I) and copper(I) complexes with bis-NHC ligands: Dinuclear complexes, cubanes and coordination polymers

Silver(I) and copper(I) complexes containing neutral bis(N-heterocyclic carbene) (NHC) ligands and coordinated or non-coordinated chloride, bromide, iodide, or tetrafluoroborate anions, were synthesised. The nature of the anions impacts deeply the structu

Synthesis of AuI- and AuIII-Bis(NHC) Complexes: Ligand Influence on Oxidative Addition to AuISpecies

The oxidation chemistry of a range of AuI-bis(NHC) (NHC = N-heterocyclic carbene) complexes with hypervalent iodine(III) oxidants has been explored. AuI-bis(NHC) precursors have been synthesised by treatment of the corresponding [Au(NHC)Cl] derivatives with imidazol(idin)ium salts in the presence of K2CO3. The reactivity of the AuIcomplexes towards PhICl2has revealed an influence of the nature of the NHC ligands present in the complex on the outcome of the oxidation reaction: small and more strongly electron-donating NHC ligands favoured the formation of a AuIIIspecies. On the basis of these results, a AuIcomplex bearing two 1-butyl-3-methylimidazol-2-ylidene (BMIM) ligands has been synthesised. This complex reacted with PhICl2and also – for the first time in Au-NHC systems – with PhI(OAc)2and PhI(OAcF)2(OAcF= trifluoroacetate), affording stable AuIII-(NHC)2complexes bearing acetate ligands.

Efficient Route to 1,3-Di-N-imidazolylbenzene. A Comparison of Monodentate vs Bidentate Carbenes in Pd-Catalyzed Cross Coupling

(Equation Presented) A new bis(carbene) ligand architecture has been developed and was evaluated in the Suzuki-Miyaura cross-coupling reaction of various aryl halides with phenylboronic acid. Several new bis(carbene) ligands were tested in different carbe

Synthesis, air stability, photobleaching, and DFT modeling of blue light emitting platinum CCC-N-heterocyclic carbene pincer complexes

The recently reported metalation/transmetalation route for the synthesis of CCC-bis(NHC) pincer ligand supported transition-metal complexes was extended to Pt. 2-(1,3-Bis(N-butylimidazol-2-ylidene)phenylene)(chloro)platinum(II) (1) and its bromo analogue 2 were synthesized and characterized. X-ray crystal structure determinations revealed complexes 1 and 2 to have distorted-square- planar configurations around the metal. Photophysical and thermal properties of these complexes are reported, and their extended photostability in air is discussed and contrasted. Density functional theory (DFT) and time-dependent density functional theory (TD-DFT) computations of the ground state and various low-lying excited states have revealed admixing of Pt 5d orbitals and the ligand π* orbitals for both the ground state and the low-lying excited states of complex 1, indicating the low-lying states to be a mixture of metal-to-ligand charge-transfer and ligand-centered transition (MLCT-LC). Somewhat surprisingly, the computed gas-phase geometry of the excited state of complex 1 had a significant distortion, mostly about the Caryl-Pt-Cl angle. These complexes were congeners of materials for organic light emitting diodes (OLEDs).

Nanoscale metallogel via self-assembly of self-assembled trinuclear coordination rings: Multi-stimuli-responsive soft materials

A rare variety of coordination rings having the M3L6 composition are prepared by the combination of Pd(NO3)2 with an imidazolyl or benzimidazolyl appended bidentate non-chelating ligand (i.e.L1 or L2). The varia

Spin-Canted Antiferromagnetic Ordering in Transition Metal-Organic Frameworks Based on Tetranuclear Clusters with Mixed V- and Y-Shaped Ligands

Four transition metal-organic frameworks were solvothermally synthesized with V-shaped 1,3-bis(1-imidazolyl)benzene (bib) and two Y-shaped carboxylate ligands (1,3,5-benzenetricarboxylic acid (H3btc) and 3,5-pyridinedicarboxylic acid (H2pydc)), namely, {[M2(μ3-OH)(bib)(btc)]·H2O}n (M = Co (1) and Fe (2)) and {[M′2(μ3-OH)(μ2-NO3)(bib)(pydc)]·solvents}n (M′ = Co (3) and Ni (4)). All of them are characterized by single-crystal X-ray diffraction, infrared spectrosopy, and powder X-ray diffraction. Both complexes 1 and 2 present two-dimensional (3,8)-connected layer structures, and the point symbol is (3.42)2(34.46.56.68.73.8), but Fe2 in 2 is weakly coordinated to O5 as a trigonal bipyramidal geometry compared with the tetrahedral Co2 in 1, while complexes 3 and 4 exhibit three-dimensional pillar-layer structures with (3,8)-connected tfz-d net. Interestingly, nitrate anions with a rare μ2-η2 coordination mode take part in coordination, and rectangular channels along the c axis exist in 3 and 4. Magnetic studies indicate that 1 and 2 present antiferromagnetic behaviors, while 3 and 4 show the coexistence of spin-canting and long-range magnetic ordering.

Directed Ortho Calciation of 1,3-Bis(3-isopropylimidazol-2-ylidene)benzene

The deprotonation of 1,3-bis(3-isopropylimidazol-2-ylidene)benzene with Me3SiCH2CaX (X = Br, I) in tetrahydrofuran (THF) yields the ether adducts of the corresponding 2,6-bis(3-isopropylimidazol-2-ylidene)phenylcalcium halides (X = B

Crystal engineering with palladium(II)-based self-assembled binuclear complexes as tectons

A series of binuclear palladium(II)-based self-assembled metallomacrocycles of Pd2L′2L2 type compositions were synthesized by complexation of an imidazole appended non-chelating bidentate ligand L with different cis-protec

ORGANOMETALLIC COMPOUND, ORGANIC LIGHT-EMITTING DEVICE INCLUDING THE SAME

The invention relates to an organometallic compound, an organic light-emitting device including the same. The organometallic compound is represented by Formula 1. The organic light-emitting device includes a first electrode, a second electrode, and an org