84-59-3

Usage

Uses

Used in Semiconductor Industry:
2,6-DIBROMO-1,5-DIHYDROXYNAPHTHALENE is used as a synthetic intermediate for the preparation of semiconducting polyphenyls and polythiophenes. These materials are essential in the development of electronic devices, such as organic solar cells and field-effect transistors, due to their unique electronic properties.
Used in Polymer Synthesis:
2,6-DIBROMO-1,5-DIHYDROXYNAPHTHALENE is used as a monomer in the synthesis of polymers containing adamantane, phenylenevinylene, or naphthalenevinylene units. These polymers have potential applications in various fields, such as materials science, pharmaceuticals, and nanotechnology, due to their unique structural and functional properties.
Used in Microwave-Assisted Suzuki and Stille Cross-Coupling Reactions:
2,6-DIBROMO-1,5-DIHYDROXYNAPHTHALENE is utilized in microwave-assisted Suzuki and Stille cross-coupling reactions, which are efficient and environmentally friendly methods for the synthesis of complex organic molecules. These reactions allow for the formation of carbon-carbon bonds, enabling the creation of a wide range of molecular structures with potential applications in various industries.

InChI:InChI=1/C10H6Br2O2/c11-7-3-1-5-6(10(7)14)2-4-8(12)9(5)13/h1-4,13-14H

Upstream product

• 83-56-7 1,5-dihydroxynaphthalene 
• 7726-95-6 bromine 
• 7553-56-2 iodine 
• 64-19-7 acetic acid 

Downstream Products

• 30413-69-5 8-amino-2,6-dibromo-5-hydroxy-[1,4]naphthoquinone 
• 91394-96-6 2,6-dibromo-1,5-bis(methoxy)naphthalene 
• 158380-97-3 2,6-dibromo-5-methoxy-[1]naphthol 
• 133546-47-1 naphtho<1,2-c:5,6-c'>bis<1,2,5>thiadiazole 
• 133546-48-2 naphtho<1,2-c:3,4-c':5,6-c''>tris<1,2,5>thiadiazole 
• 93831-65-3 9-bromo-3-phenylnaphtho<1,8-bc>pyran-2,6-dione 
• 93831-64-2 5,9-dibromo-3-phenylnaphtho<1,8-bc>pyran-2,6-dione 
• 85337-31-1 2,6-Dibromo-1,5-bis<(p-tolylsulfonyl)oxy>naphthalene 
• 93831-66-4 5,10-dibromo-3,8-diphenylnaphtho<1,8-bc:4,5-b'c'>dipyran-2,7-dione 
• 1227744-54-8 2,6-dibromo-1,5-bis(phenylethynyl)naphthalene 
• 1195142-25-6 2,7-diphenylnaphtho[2,1-b:6,5-b']dithiophene 
• 1414857-98-9 C₃₈H₃₀N₂O₆ 
• 1414857-92-3 C₃₈H₃₀N₂O₂ 
• 1414857-97-8 C₂₆H₂₀Br₂N₂O₆ 

Relevant academic research and scientific papers

Development of bulk heterojunction morphology by the difference of intermolecular interaction behaviors

The morphology of a bulk heterojunction can be controlled by adding a processing additive in order to improve its power conversion efficiency (PCE) in photovoltaic devices. The phase-separated morphologies of blends of PONTBT or P3HT with fullerene derivatives are systematically examined in the presence of processing additives that possess various alkane alkyl chain lengths or end-group electronegativities. We determined the morphologies of the bulk heterojunction layers by using atomic force microscopy (AFM) and grazing incidence wide angle X-ray scattering (GIWAXS). The photocurrent-voltage characteristics of the bulk heterojunction solar cells were found to be strongly dependent on the intermolecular interactions between the conjugated polymers, the fullerene derivatives, and the processing additives in the photoactive layer. The optimal PONTBT:fullerene derivative blend morphology was obtained with a processing additive, 1,3-diiodopropane (1,3-DIP), that possesses a short alkyl chain and an end group with weak electronegativity, and was found to exhibit a high fill factor (FF) and a high current density (JSC). In contrast, in blends of P3HT with the fullerene derivative, PCEs with higher FF and JSC values were achieved by incorporating the processing additive, 1,8-dibromooctane (1,8-DBrO), which has a long alkyl chain and a strong electronegative end group. Thus the selection of the processing additive with the aim of enhancing photovoltaic performance needs to take into account the intermolecular interaction of the conjugated polymer.

Synthesis and characterization of tetraoctyloxy substituted naphthalenophanedienes

Tetraoctyloxy-substituted naphthalenophanedienes were synthesized from tetraoctyloxy-substituted dithia[3.3]naphthalenophanes via sequential benzyne Stevens rearrangement, oxidation, and pyrolysis reactions. Surprisingly, only the pseudo-geminal isomer of tetraoctyloxy-substituted dithia[3.3]naphthalenophane was obtained after cyclization of the corresponding starting materials. The structures of the pseudo-geminal isomers of tetraoctyloxy-substituted dithia[3.3]naphthalenophane and tetraoctyloxy-substituted naphthalenophanediene were fully determined by nuclear magnetic resonance spectroscopy, high resolution mass spectrometry, and X-ray crystallography. The pseudo-geminal and pseudo-meta diastereomers of tetraoctyloxy-substituted naphthalenophanedienes were isolated by multiple fractional recrystallization from hexane at 5 °C. The solid state structure of the pseudo-geminal isomer of tetraoctyloxy-substituted naphthalenophanediene revealed strongly distorted naphthyl rings with high levels of ring strain.

Convenient regioselective syntheses of isomeric bis(tetrathiafulvalenylethenyl)naphthalene π-donors

Novel highly soluble isomeric tetrathiafulvalene (TTF) dimers with unusual divinylnaphthalene spacers have been prepared from Wittig reactions. The cyclic voltammetry of the new TTF dimers reveals an independent behaviour of the two TTF units which show different oxidation potential values depending upon the substitution pattern.

From Colorless to Near-Infrared S-Heteroarene Isomers: Unexpected Cycloaromatization of Cyclopenta[ b]thiopyran Catalyzed by PtCl2

S-heteroarenes containing cyclopenta[b]thiopyran moieties were synthesized via intramolecular ring-expanding cycloisomerization from 1-acetyl-2-thienyl-substituted precursors catalyzed by PtCl2. In comparison to the other two S-heteroarene isomers experiencing common 6-endo and 5-exo cyclization processes, the aromatic cyclopenta[b]thiopyran derivative demonstrates intriguing photophysical and electrochemical properties, such as near-infrared absorption, low oxidation potential, and excellent electrochemical stability. Therefore, this work provides an effective pathway to incorporate cyclopenta[b]thiopyran as building blocks for organic semiconductors with unique properties.

Highly Fluorescent Red-Light Emitting Bis(boranils) Based on Naphthalene Backbone

Ten bis(boranils) differently substituted at the boron atom and iminophenyl groups were synthesized from 1,5-dihydroxynaphthalene-2,6-dicarboxaldehyde using a simple one-pot protocol. Their photophysical properties can be easily tuned in a wide range by the variation of substituents. Their absorption and emission spectral bands are significantly red-shifted (λmax = 495-590 nm, λem = 533-683 nm) when compared with simple boranils, whereas fluorescence quantum yields are strongly improved to reach 83%. The attachment of pendant NO2 and NEt2 groups at the opposite positions of the π-conjugated bis(boranil) scaffold resulted in the formation of an unprecedented system featuring push-pull architecture.

Gas adsorption properties of highly porous metal-organic frameworks containing functionalized naphthalene dicarboxylate linkers

Three functionalized metal-organic frameworks (MOFs), MOF-205-NH2, MOF-205-NO2, and MOF-205-OBn, formulated as Zn4O(BTB)4/3(L), where BTB is benzene-1,3,5-tribenzoate and L is 1-aminonaphthalene-3,7-dicarboxylate (NDC-NH2), 1-nitronaphthalene-3,7-dicarboxylate (NDC-NO2) or 1,5-dibenzyloxy-2,6-naphthalenedicarboxylate (NDC-(OBn)2), were synthesized and their gas (H2, CO2, or CH4) adsorption properties were compared to those of the un-functionalized, parent MOF-205. Ordered structural models for MOF-205 and its derivatives were built based on the crystal structures and were subsequently used for predicting porosity properties. Although the Brunauer-Emmett-Teller (BET) surface areas of the three MOF-205 derivatives were reduced (MOF-205, 4460; MOF-205-NH2, 4330; MOF-205-NO2, 3980; MOF-205-OBn, 3470 m2 g-1), all three derivatives were shown to have enhanced H2 adsorption capacities at 77 K and CO2 uptakes at 253, 273, and 298 K respectively at 1 bar in comparison with MOF-205. The results indicate the following trend in H2 adsorption: MOF-205 2 2 2/N2 (15/85 in v/v) and 2.7 for CO2/CH4 (50/50 in v/v) at 298 K. Despite the large reduction (-22%) in the surface area, MOF-205-OBn displayed comparable total volumetric CO2 (at 48 bar) and CH4 (at 35 bar) storage capacities with those of MOF-205 at 298 K: MOF-205-OBn, 305 (CO2) and 112 (CH4) cm3 cm-3, and for MOF-205, 307 (CO2) and 120 (CH4) cm3 cm-3, respectively.

A photoresponsive planar chiral azobenzene dopant with high helical twisting power

A planar chiral molecule as a photon-mode chiral switch was synthesized for the reversible control of self-assembled superstructures based on doped chiral nematic liquid crystals. The chiral switch is composed of bis-hexyl substituted diphenylnaphthalene and a photoisomerizing azobenzene unit connected by ethylene spacers in a cyclic manner. Bis-hexyl substitution to the mesogenic unit promoted the chirality transfer to the host LC medium resulting in a high initial helical twisting power (HTP) and a large change in HTP by photo-isomerization of the chiral dopant. At very low doping concentrations, both reversible tuning of RGB reflection colors and rotation motion control of micro glass rods on the cholesteric liquid crystal surface were achieved.

NOVEL FUSED NAPHTHALENE CYCLOHETERO RING COMPOUNDS, AND METHODS AND USES THEREOF

Described herein are heterocyclic organic compounds. More specifically, described herein are fused heterocyclic naphthalene compounds, polymers based on fused heterocyclic naphthalene compounds, methods for making these compounds, and uses thereof. The compounds described have improved polymerization and stability properties that allow for improved material processibility.

Emission and transient absorption measurements of substitution effects of C-C triple bonds on relaxation processes of the fluorescent state of naphthalenes

Photophysical and photochemical properties of naphthalenes substituted with trimethylsilylethynyl, tert-butylethynyl, and trimethylsilylbutadiynyl groups were investigated by measurement of fluorescence yields, lifetimes, and triplet absorption. Introducing trimethylsilylethynyl and tert-butylethynyl groups to the 1-position of the naphthalene skeleton substantially enhanced fluorescence and intersystem crossing (ISC). The rates of fluorescence of 2-substituted naphthalenes were low. The effect of ethynyl groups on the 1-substituted naphthalenes was rationalized in terms of an increase of the transition moment along the short axis of the naphthalene skeleton. Substitution of the trimethylsilylbutadiynyl group at the 1 or 2-position of the naphthalene skeleton caused a considerable decrease in the fluorescence yield (approximately 0.01) and an increase in the ISC yield (0.99).

Isomeric carbazolocarbazoles: Synthesis, characterization and comparative study in Organic Field Effect Transistors

We report here the synthesis and characterization of a new family of isomeric carbazolocarbazole derivatives, namely carbazolo[1,2-a]carbazole, carbazolo[3,2-b]carbazole and carbazolo[4,3-c]carbazole. Thermal, optical, electrochemical, morphological and semiconducting properties have been studied to understand the influence of geometrical isomerism on the optoelectronic properties of these compounds. Different packing patterns have been observed by single crystal X-ray diffraction (XRD) which then correlate with the different morphologies of the evaporated thin films studied by XRD and Atomic Force Microscopy (AFM). The effect of N-substituents has also been evaluated for one of the isomers revealing a noticeable influence on the performance as organic semiconductors in Organic Field Effect Transistors (OFETs). A good p-channel field effect has been determined for N,N′-dioctylcarbazolo[4,3-c]carbazole with a mobility of 0.02 cm2 V-1 s-1 and I on/Ioff ratio of 106 in air. These preliminary results demonstrate the promising properties of molecular carbazolocarbazole systems which should be further explored in the area of organic semiconducting materials.