117490-52-5

Usage

Uses

Used in Electronic and Optical Materials Industry:
2,2'-dimethyl-4,4'-biphenyldicarboxylic acid is used as a monomer for the production of liquid crystalline polymers (LCPs) in the electronic and optical materials industry. 2,2'-dimethyl-4,4'-biphenyldicarboxylic acid provides enhanced thermal stability, rigidity, and chemical resistance to the LCPs, making them suitable for high-performance applications in this industry.
Used in Specialty Resins Production:
2,2'-dimethyl-4,4'-biphenyldicarboxylic acid is used as a key component in the production of specialty resins. Its unique chemical structure and performance characteristics contribute to the development of advanced materials with superior mechanical and thermal properties, which are essential for various applications in the specialty resins industry.
Used in Adhesives and Coatings Industry:
2,2'-dimethyl-4,4'-biphenyldicarboxylic acid is utilized in the production of adhesives and coatings due to its unique chemical structure and performance characteristics. 2,2'-dimethyl-4,4'-biphenyldicarboxylic acid enhances the thermal stability, rigidity, and chemical resistance of the resulting products, making them suitable for various high-performance applications in the adhesives and coatings industry.

Upstream product

• 31458-18-1 dimethyl 2,2′-dimethyl-[1,1′-biphenyl]-4,4′-dicarboxylate 
• 148547-19-7 4-Bromo-3-methylbenzoic acid methyl ester 
• 473596-87-1 4-methoxycarbonyl-2-methylbenzeneboronic acid pinacol ester 
• 5471-81-8 methyl 4-iodo-3-methylbenzoate 

Relevant academic research and scientific papers

Discovery of spontaneous de-interpenetration through charged point-point repulsions

Energetically driven reduction of porosity through entanglement is ubiquitous in nature and synthetic systems. This entanglement decreases valuable internal pore space useful for applications, such as catalysis, storage, and sensing. Here, we describe the discovery of spontaneous de-interpenetration in a 6-fold interpenetrated uranium-based metal-organic framework (MOF), NU-1303-6. De-interpenetration transforms NU-1303-6 (14.2 and 19.8 ? pores) to its larger pore (40.7 ?) non-interpenetrated counterpart, which possesses a record-high 96.6% void fraction and 9.2 cm3g?1 pore volume. Density functional theory calculations reveal that charged point-point repulsions between anionic, closely positioned uranium-based nodes drive this phenomenon. These repulsions compete with water molecules that hydrogen bond nearby networks together, favoring interpenetration. Controlling the interplay between these intermolecular forces enables the reversal of omnipresent energetic equilibria, leading to thermodynamically favored open pore structures. The discovery of charged point-point repulsion will likely lead to the re-evaluation of non-interpenetrated network design, synthesis, and wide-reaching applications.

Mimicking the Electron Transport Chain and Active Site of [FeFe] Hydrogenases in One Metal-Organic Framework: Factors That Influence Charge Transport

[FeFe] hydrogenase (H2ase) enzymes are effective proton reduction catalysts capable of forming molecular dihydrogen with a high turnover frequency at low overpotential. The active sites of these enzymes are buried within the protein structures, and substrates required for hydrogen evolution (both protons and electrons) are shuttled to the active sites through channels from the protein surface. Metal-organic frameworks (MOFs) provide a unique platform for mimicking such enzymes due to their inherent porosity which permits substrate diffusion and their structural tunability which allows for the incorporation of multiple functional linkers. Herein, we describe the preparation and characterization of a redox-active PCN-700-based MOF (PCN = porous coordination network) that features both a biomimetic model of the [FeFe] H2ase active site as well as a redox-active linker that acts as an electron mediator, thereby mimicking the function of [4Fe4S] clusters in the enzyme. Rigorous studies on the dual-functionalized MOF by cyclic voltammetry (CV) reveal similarities to the natural system but also important limitations in the MOF-enzyme analogy. Most importantly, and in contrast to the enzyme, restrictions apply to the total concentration of reduced linkers and charge-balancing counter cations that can be accommodated within the MOF. Successive charging of the MOF results in nonideal interactions between linkers and restricted mobility of charge-compensating redox-inactive counterions. Consequently, apparent diffusion coefficients are no longer constant, and expected redox features in the CVs of the materials are absent. Such nonlinear effects may play an important role in MOFs for (electro)catalytic applications.

Flexible Microporous Copper(II) Metal-Organic Framework toward the Storage and Separation of C1-C3 Hydrocarbons in Natural Gas

A flexible and robust microporous copper(II) metal-organic framework (MOF) based on a methyl-functionalized ligand, namely, [Cu3(μ3-OH)2(L)2(DMF)] (LIFM-ZZ-1; L = 2,2′-dimethyl-4,4′-biphenyldicarboxylic acid and DMF = N,N-dimethylformamide), was constructed. Its sorption performance for the separation of CH4, C2H6, and C3H8 was investigated. LIFM-ZZ-1 showed a breathing behavior that led to a transition between large- and narrow-pore states. The sample also showed outstanding water stability. Gas adsorption experiments revealed that desolvated LIFM-ZZ-1 exhibited higher adsorption capacities for C2H6 and C3H8 (2.80 and 4.06 mmol·g-1) than for CH4 (0.39 mmol·g-1) at 298 K and 1 bar. Breakthrough experiments showed that a CH4/C2H6/C3H8 mixture was completely separated at 298 K, demonstrating the promising potential applications of this material for separating low contents of C2/C3 hydrocarbons from natural gas.

Diverse Multi-Functionalized Oligoarenes and Heteroarenes for Porous Crystalline Materials

A modular synthesis of multi-functionalized biphenyl, terphenyl and higher linear oligophenylene dicarboxylic acids and pyridine-terminated oligoarenes by stepwise palladium–catalyzed borylation/Suzuki–Miyaura cross-coupling reactions is described. The presence of several distinct functional groups such as azide, hydroxy, and alkyne, as well as coordinative functional end groups (carboxylic acid or pyridine) combined in a single oligoarene molecular unit at strategic positions offer an advantageous dual-utility. First, these compounds can serve as useful molecular bricks (ditopic organic linkers) in the construction of complex porous crystalline materials. Second, after the assembly into the crystalline coordination networks, orthogonal functional sites within the linker-backbone offer tremendous potential from application perspectives as they can be modified by a wide range of post-synthetic modifications including azide–alkyne click chemistry. This allows further tailoring of the supramolecular assemblies to yield novel multifunctional materials.

Tuning the Ionicity of Stable Metal-Organic Frameworks through Ionic Linker Installation

The predictable topologies and designable structures of metal-organic frameworks (MOFs) are the most important advantages for this emerging crystalline material compared to traditional porous materials. However, pore-environment engineering in MOF materia

Flexible Zirconium MOFs as Bromine-Nanocontainers for Bromination Reactions under Ambient Conditions

A series of flexible MOFs (PCN-605, PCN-606, and PCN-700) are synthesized and applied to reversible bromine encapsulation and release. The chemical stability of these Zr-MOFs ensures the framework's integrity during the bromine adsorption, while the framework's flexibility allows for structural adaptation upon bromine uptake to afford stronger host–guest interactions and therefore higher bromine adsorption capacities. The flexible MOFs act as bromine-nanocontainers which elongate the storage time of volatile halides under ambient conditions. Furthermore, the bromine pre-adsorbed flexible MOFs can be used as generic bromine sources for bromination reactions giving improved yields and selectivities under ambient conditions when compared with liquid bromine.

Linker Installation: Engineering Pore Environment with Precisely Placed Functionalities in Zirconium MOFs

Precise placement of multiple functional groups in a highly ordered metal-organic framework (MOF) platform allows the tailoring of the pore environment, which is required for advanced applications. To realize this, we present a comprehensive study on the linker installation method, in which a stable MOF with coordinatively unsaturated Zr6 clusters was employed and linkers bearing different functional groups were postsynthetically installed. A Zr-MOF with inherent missing linker sites, namely, PCN-700, was initially constructed under kinetic control. Twelve linkers with different substituents were then designed to study their effect on MOF formation kinetics and therefore resulting MOF structures. Guided by the geometrical analysis, linkers with different lengths were installed into a parent PCN-700, giving rise to 11 new MOFs and each bearing up to three different functional groups in predefined positions. Systematic variation of the pore volume and decoration of pore environment were realized by linker installation, which resulted in synergistic effects including an enhancement of H2 adsorption capacities of up to 57%. In addition, a size-selective catalytic system for aerobic alcohol oxidation reaction is built in PCN-700 through linker installation, which shows high activity and tunable size selectivity. Altogether, these results exemplify the capability of the linker installation method in the pore environment engineering of stable MOFs with multiple functional groups, giving an unparalleled level of control.

Flexible Zirconium Metal-Organic Frameworks as Bioinspired Switchable Catalysts

Flexible metal–organic frameworks (MOFs) are highly desirable in host–guest chemistry owing to their almost unlimited structural/functional diversities and stimuli-responsive pore architectures. Herein, we designed a flexible Zr-MOF system, namely PCN-700 series, for the realization of switchable catalysis in cycloaddition reactions of CO2with epoxides. Their breathing behaviors were studied by successive single-crystal X-ray diffraction analyses. The breathing amplitudes of the PCN-700 series were modulated through pre-functionalization of organic linkers and post-synthetic linker installation. Experiments and molecular simulations confirm that the catalytic activities of the PCN-700 series can be switched on and off upon reversible structural transformation, which is reminiscent of sophisticated biological systems such as allosteric enzymes.

Encapsulation of dyes in metal-organic frameworks and their tunable nonlinear optical properties

Two series of cationic dyes, named DM-n and DP-n, were encapsulated in three anionic isostructural MOFs with a 1D channel. Ordered arrangement of the dyes in the channel was investigated by using the microscope polarized absorption spectra of different dye and MOF composites. Furthermore, the tunable second order nonlinear optical properties of these MOF ? dye materials were observed.

Sequential linker installation: Precise placement of functional groups in multivariate metal-organic frameworks

A unique strategy, sequential linker installation (SLI), has been developed to construct multivariate MOFs with functional groups precisely positioned. PCN-700, a Zr-MOF with eight-connected Zr6O4(OH)8(H2O)4 clusters, has been judiciously designed; the Zr6 clusters in this MOF are arranged in such a fashion that, by replacement of terminal OH-/H2O ligands, subsequent insertion of linear dicarboxylate linkers is achieved. We demonstrate that linkers with distinct lengths and functionalities can be sequentially installed into PCN-700. Single-crystal to single-crystal transformation is realized so that the positions of the subsequently installed linkers are pinpointed via single-crystal X-ray diffraction analyses. This methodology provides a powerful tool to construct multivariate MOFs with precisely positioned functionalities in the desired proximity, which would otherwise be difficult to achieve.