20027-95-6

Usage

Uses

Used in Organic Synthesis:
1,5-DIBROMO-2,6-DIMETHYL-NAPHTHALENE is used as an intermediate in the synthesis of various organic compounds, contributing to the formation of a wide array of chemical products due to its reactive bromine and methyl groups.
Used in Research and Development:
In the realm of organic chemistry, 1,5-DIBROMO-2,6-DIMETHYL-NAPHTHALENE is utilized as a reagent, facilitating scientific exploration and the advancement of chemical knowledge through its involvement in experimental procedures and reactions.
Used in Chemical Industry:
1,5-DIBROMO-2,6-DIMETHYL-NAPHTHALENE is employed as a building block for creating more complex molecules, which are essential in the development of new materials and pharmaceuticals.
Safety Considerations:

InChI:InChI=1S/C12H10Br2/c1-7-3-5-10-9(11(7)13)6-4-8(2)12(10)14/h3-6H,1-2H3

Upstream product

• 581-42-0 2.6-dimethylnaphthalene 
• 75-15-0 carbon disulfide 
• 7726-95-6 bromine 

Downstream Products

• 85477-63-0 1,5-dibromo-2,6-bis(bromomethyl)naphthalene 
• 1228673-47-9 C₂₄H₁₈Br₂ 
• 1228673-48-0 C₂₄H₁₄Br₂O₄ 
• 1380099-45-5 C₄₀H₁₆F₁₂O₂ 
• 59950-04-8 dimethyl 1,5-dibromonaphthalene-2,6-dicarboxylate 
• 1357448-15-7 N,N'-bis-(4-(trifluoromethyl)phenyl)naphthalene-1,2,5,6-bis(dicarboxamide) 
• 1357448-17-9 N,N'-bis(perfluorophenethyl)-1,2,5,6-naphthalenetetracarboxyl diimide 
• 1357448-16-8 N,N'-bis (4-(trifluoromethyl)phenethyl)-1,2,5,6-naphthalenetetracarboxyl diimide 
• 29041-32-5 <2.2> (2,6)naphthalenophane (achiral) 

Relevant academic research and scientific papers

Naphtho[1,2-c;5,6-c]difuran, a stable isobenzofuran derivative

The title compound, an interesting analog of isobenzofuran, was prepared in nine steps from 2,6-dimethylnaphthalene in an overall yield of 12%. Copyright (C) 1996 Elsevier Sciences Ltd.

Conformational studies by dynamic NMR. 42. Detection of meso and racemic conformers resulting from a chirality created by the restricted torsion of hindered carbonyls

Aromatic derivatives containing two equivalent, sterically hindered, carbonyl groups can exist either as meso or as racemic (d, l) conformers, owing to the noncoplanarity of the Ar and RC = O moieties which creates two centers of chirality.Molecular Mechanics calculations (MM-2) carried out on 2,6-dimethyl-1,5-di(2-methyl)propanoylnaphthalene (1) suggest that the meso form is only 0.5 kcal*mol-1 (1 kcal = 4.184 J) more stable than the racemic conformer.Solid-state nmr spectra on a bulk sample are not in contrast with the result of the X-ray analysis on a single crystal that the meso conformer is the only species which is present in the solid.On the other hand low-temperature nmr spectra showed that both meso and racemic conformers are present in solution (e.g., 57percent and 43percent in CD2Cl2 at -85deg), the corresponding interconversion barrier (as determined by line shape computer simulation) being 10.7 kcal * mol-1.

Generation of C10H4 species in a low-temperature argon matrix: Consecutive photolysis of 1,2;5,6-naphthalenetetracarboxylic dianhydride

1,2;5,6-Naphthalenetetracarboxylic dianhydride has been consecutively photolyzed in a low-temperature argon matrix by wavelength-selective irradiation; dec-5-ene-1,3,7,9-tetrayne, which is the second C10H4 isomer, was generated as the final product.

On-surface synthesis of super-heptazethrene

Zethrenes are model diradicaloids with potential applications in spintronics and optoelectronics. Despite a rich chemistry in solution, on-surface synthesis of zethrenes has never been demonstrated. We report the on-surface synthesis of super-heptazethrene on Au(111). Scanning tunneling spectroscopy investigations reveal that super-heptazethrene exhibits an exceedingly low HOMO-LUMO gap of 230 meV and, in contrast to its open-shell singlet ground state in the solution phase and in the solid-state, likely adopts a closed-shell ground state on Au(111). This journal is

Strain-Induced Isomerization in One-Dimensional Metal–Organic Chains

The ability to use mechanical strain to steer chemical reactions creates completely new opportunities for solution- and solid-phase synthesis of functional molecules and materials. However, this strategy is not readily applied in the bottom-up on-surface synthesis of well-defined nanostructures. We report an internal strain-induced skeletal rearrangement of one-dimensional (1D) metal–organic chains (MOCs) via a concurrent atom shift and bond cleavage on Cu(111) at room temperature. The process involves Cu-catalyzed debromination of organic monomers to generate 1,5-dimethylnaphthalene diradicals that coordinate to Cu adatoms, forming MOCs with both homochiral and heterochiral naphthalene backbone arrangements. Bond-resolved non-contact atomic force microscopy imaging combined with density functional theory calculations showed that the relief of substrate-induced internal strain drives the skeletal rearrangement of MOCs via 1,3-H shifts and shift of Cu adatoms that enable migration of the monomer backbone toward an energetically favorable registry with the Cu(111) substrate. Our findings on this strain-induced structural rearrangement in 1D systems will enrich the toolbox for on-surface synthesis of novel functional materials and quantum nanostructures.

1,2,5,6-naphthalenediimide based donor-acceptor copolymers designed from isomer chemistry for organic semiconducting materials

Two new donor-acceptor (D-A) copolymers based on 1,2,5,6- naphthalenediimides (iso-NDI) and thiophene units, iso-P(NDI2OD-T2) and iso-P(NDI2OD-TT), were designed from isomer chemistry and compared with the reported isomeric copolymers P(NDI2OD-T2) and P(NDI2DT-TT) to investigate the influence of isomeric structure on their optoelectronic properties. DFT calculations reveal that iso-P(NDI2OD-T2) and iso-P(NDI2OD-TT) have higher HOMO and LUMO energies and better backbone planarity relative to their isomeric polymers. Iso-P(NDI2OD-T2) and iso-P(NDI2OD-TT) were synthesized by the Stille coupling polymerization and characterized by elemental analysis, 1H NMR, GPC, UV-vis absorption, cyclic voltammetry, TGA, DSC, and organic thin film transistors (OTFTs). It was found that iso-P(NDI2OD-T2) and iso-P(NDI2OD-TT) had higher LUMO energies and broader band gaps than their isomeric ones and showed hole-dominated charge transport behavior, which is quite different from the electron-dominated charge transport feature of P(NDI2OD-T2) and P(NDI2DT-TT). In spite of the amorphous-like thin-film features, iso-P(NDI2OD-T2) exhibited high hole mobility of up to 0.3 cm2 V -1 s-1, and iso-P(NDI2OD-TT) showed ambipolar property with hole and electron mobility of up to 0.02 and 4 × 10-3 cm2 V-1 s-1, respectively.

THIENO-INDENO-MONOMERS AND POLYMERS

Polymers comprising at least one unit of formulae 1 or 1' and compounds of the formulae 2 or 2' wherein, in formulae 1, 1', 2 and 2', n is 0, 1, 2, 3 or 4, m is 0, 1, 2, 3 or 4, M1 and M2 are independently of each other an aromatic or heteroaromatic monocyclic or bicyclic ring system; X is at each occurrence selected from the group consisting of O, S, Se or Te, Q is at each occurrence selected from the group consisting of C, Si or Ge, R is at each occurrence selected from the group consisting of hydrogen, C1-100-alkyl, C2-100-alkenyl, C2-100-alkynyl, C5-12-cycloalkyl, C6-18-aryl, a 5 to 20 membered heteroaryl, C(O)-C1-100-alkyl, C(O)-C5-12-cycloalkyl and C(O)-OC1-100-alkyl. R2, R2', R2", R* are at each occurrence independently selected from the group consisting of hydrogen, C1-30-alkyl, C2-30-alkenyl, C2-30-alkynyl, C5-12-cycloalkyl, C6-18-aryl, 5 to 20 membered heteroaryl, OR21, OC(O)-R21, C(O)-OR21, C(O)-R21, NR21R22, NR21-C(O)R22, C(O)-NR21R22,N[C(O)R21][C(O)R22], SR21, halogen, CN, SiRSisRSitRSiu and OH, L1 and L2 are independently from each other and at each occurrence selected from the group consisting of C6-30-arylene, 5 to 30 membered heteroarylene, (A) (B) and (C).

Nonplanar Ladder-Type Polycyclic Conjugated Molecules: Structures and Solid-State Properties

Using an efficient intramolecular carbon-carbon cross-coupling reaction, a series of new ladder-type conjugated molecules have been prepared successfully in high yields. Such a pyran-fused polycylic structure possesses an extended π-conjugated backbone with flexible conformation, which gives these molecules interesting properties, including high solubility in common organic solvents, excellent thin film-forming abilities, blue fluorescent emission with good quantum yields, and aggregate formation in a binary solvent. The self-assembly behaviors of these molecules as well as various nanostructures can be finely tailored by varying the substituted group on the molecular periphery. The powder and single-crystal X-ray diffraction analyses revealed that the synergetic effect of π-π stacking and van der Waals interactions play a key role in controlling the morphologies of these aggregates. More importantly, self-assembled molecules exhibit good fluorescent performance, due to their twist backbone conformation. (Figure Presented).

Gold(I) styrylbenzene, distyrylbenzene, and distyrylnaphthalene complexes: High emission quantum yields at room temperature

One gold(I)-substituted styrylbenzene, six digold(I) distyrylbenzenes, one tetragold distyrylbenzene, and four digold distyrylnaphthalene complexes were synthesized using base-promoted auration, alkynylation, triazolate formation, and Horner-Wadsworth-Emmons reactions. The gold(I) fragments are either σ-bonded to the aromatic system, or they are attached through an alkynyl or triazolate spacer. Product formation was monitored using 31P{ 1H} NMR spectroscopy. Systems in which gold(I) binds to the central benzene ring or the terminal phenyl rings were designed. All of these complexes have strong ultraviolet absorptions and emit blue light. The position of the gold(I) attachment influences the luminescence efficiency. Complexes with two gold(I) fragments attached to the ends of the conjugated system have fluorescence quantum yields up to 0.94, when using 7-diethylamino-4- methylcoumarin as the emission standard. Density-functional theory calculations on three high-yielding emitters suggest that luminescence originates from the distyrylbenzene or -naphthalene bridge. Copyright

Molecular tuning of phenylene-vinylene derivatives for two-photon photosensitized singlet oxygen production

(Chemical Equation Presented) Substituent-dependent features and properties of the sensitizer play an important role in the photosensitized production of singlet oxygen, O2(a1Δg). In this work, we systematically examine the effect of molecular changes in the sensitizer on the efficiency of singlet oxygen production using, as the sensitizer, oligophenylene-vinylene derivatives designed to optimally absorb light in a nonlinear two-photon process. We demonstrate that one cannot always rely on rule-of-thumb guidelines when attempting to construct efficient two-photon singlet oxygen sensitizers. Rather, as a consequence of behavior that can deviate from the norm, a full investigation of the photophysical properties of the system is generally required. For example, it is acknowledged that the introduction of a ketone moiety to the sensitizer chromophore often results in more efficient production of singlet oxygen. However, we show here that the introduction of a carbonyl into a given phenylene-vinylene can, rather, have adverse effects on the yield of singlet oxygen produced. Using these molecules, we show that care must also be exercised when using qualitative symmetry-derived arguments to predict the relationship between one-and two-photon absorption spectra.