239-30-5

Usage

Uses

Used in Environmental Monitoring:
Benzo[b]naphtho[2,1-d]furan is used as a biomarker for assessing the presence of PAHs in the environment. Its detection in air, water, and soil samples can indicate exposure to pollutants from incomplete combustion of organic materials, such as fossil fuels, wood, and tobacco.
Used in Industrial Emission Control:
Benzo[b]naphtho[2,1-d]furan is used as a target compound for monitoring and controlling industrial emissions. Industries that emit PAHs, such as those involved in the production of fossil fuels, chemicals, and tobacco products, are required to implement measures to reduce the release of BNF and other harmful pollutants into the environment.
Used in Public Health and Safety:
Benzo[b]naphtho[2,1-d]furan is used as a reference substance in public health and safety guidelines. Its identification in various sources, such as vehicle exhaust, cigarette smoke, and industrial emissions, helps to raise awareness about the potential health risks associated with exposure to PAHs and encourages the implementation of preventive measures to protect human health.

InChI:InChI=1S/C16H10O/c1-2-6-12-11(5-1)9-10-14-13-7-3-4-8-15(13)17-16(12)14/h1-10H

Upstream product

• 109396-47-6 (2-phenyl-benzofuran-3-yl)-pyruvic acid 
• 51171-00-7 10-(2-Phenyl-benzofuran-3-yl-methylcarbonyloxy)-dibenzo-benzofuran 
• 159052-03-6 (E)-1-(2-Methoxy-phenyl)-4-phenyl-1-(triphenyl-λ⁵-phosphanylidene)-but-3-en-2-one 
• 613669-18-4 2-(naphthalen-1-yloxy)-benzoic acid 
• 1245937-16-9 1-naphthyl 2-(allyloxy)benzoate 
• 90-15-3 α-naphthol 
• 1165952-91-9 cyclohexa-1,3-diene 
• 20841-63-8 7,8,9,10-tetrahydronaphtho<1,2-b>benzofuran 
• 871817-14-0 2-(2-chlorophenyl)-1,3,2-dioxaborolane 
• 573-57-9 1,4-dihydronaphthalene-1,4-epoxide 
• 78210-35-2 2-(2-hydroxyphenyl)naphthalene 
• 67-56-1 methanol 
• 93321-12-1 2-(2'-methoxyphenyl)naphthalene 
• 5720-06-9 2-Methoxyphenylboronic acid 

Downstream Products

• 101279-19-0 2-(2-carboxy-phenyl)-benzofuran-3-carboxylic acid 
• 199-24-6 benzo[a]benzo[4,5]furo[2,3-c]phenazine 
• 1256544-81-6 5-(3-bromophenyl)benzo[b]naphtho[2,1-d]furan 
• 1377575-06-8 C₃₅H₂₂N₂O 

Relevant academic research and scientific papers

Regioselective arene homologation through rhenium-catalyzed deoxygenative aromatization of 7-oxabicyclo[2.2.1]hepta-2,5-dienes

Combined use of oxorhenium catalysts with triphenyl phosphite as an oxygen acceptor allowed efficient deoxygenative aromatization of oxabicyclic dienes. The reaction proceeded under neutral conditions and was compatible with various functional groups. Combining this deoxygenation with regioselective bromination and trapping of the generated aryne with furan resulted in benzannulative π-extension at the periphery of the PAHs. This enabled direct use of unfunctionalized PAHs for extension of π-conjugation. Iteration of the transformations increased the number of fused-benzene rings one at a time, which has the potential to alter the properties of PAHs by fine-tuning the degree of π-conjugation, shape, and edge topology.

Pd-Catalyzed Denitrative Intramolecular C-H Arylation

A Pd-catalyzed intramolecular C-H arylation of nitroarenes has been developed. Nitroarenes bearing tethered aryl groups at the ortho-position can be readily prepared in one step from 2-halonitroarenes by a nucleophilic aromatic substitution (SNAr). Under Pd/BrettPhos catalysis, activations of the C-NO2 bond as well as the C-H bond on arenes generated the corresponding biaryl linkage in moderate to excellent yields.

ORGANIC COMPOUND, ORGANIC OPTOELECTRIC DIODE, AND DISPLAY DEVICE

The present invention relates to an organic compound represented by Chemical Formula 1, an organic optoelectronic diode, and a display device.

Heterotetracenes: Flexible Synthesis and in Silico Assessment of the Hole-Transport Properties

Thienoacenes and furoacenes are among the most frequent molecular units found in organic materials. The efficient synthesis of morphologically different heteroacenes and the rapid determination of their solid-state and electronic properties are still challenging tasks, which slow down progress in the development of new materials. Here, we report a flexible and efficient synthesis of unprecedented heterotetracenes based on a platinum- and gold-catalyzed cyclization–alkynylation domino process using EthynylBenziodoXole (EBX) hypervalent iodine reagents in the key step. The proof-of-principle in silico estimation of the synthesized tetracenes’ charge transport properties reveals their strong dependence on both the position and nature of the heteroatoms in the ring system. A broad range of mobility is predicted, with some compounds displaying performance potentially comparable to that of state-of-the-art electronic organic materials.

NMR and DFT studies on persistent carbocations derived from benzo[kl]xanthene, dibenzo[d,d′]benzo[1,2-b:4,3-b′]difuran, and dibenzo[d,d′]benzo[1,2-b:4,5-b′]difuran in superacidic media

Persistent carbocations generated by the protonation of hetero-polycyclic aromatic compounds with oxygen atom(s) were studied by experimental NMR and density function theory calculations. Benzo[kl]xanthene (1), dibenzo[d,d′]benzo[1,2-b:4,3-b′]difuran (2), and dibenzo[d,d′]benzo[1,2-b:4,5-b′]difuran (3) were synthesized by the annulation of arenediazonium salts. Compound 1 in FSO3H-SbF5 (4:1)/SO2ClF and 3 in FSO3H-SbF5 (1:1)/SO2ClF ionized to 1aH+ with protonation at C(4) and to 3aH+ with protonation at C(6), and these cations were successfully observed by NMR at low temperatures. The density function theory calculations indicated that 1aH+ and 3aH+ were the most stable protonated carbocations and that 2 should ionize to 2aH+ with protonation at C(6). According to the changes in 13C chemical shifts (Δδ13C), the positive charge was delocalized into the naphthalene unit for 1aH+, into one benzo[b,d]furan unit for 2aH+, and into one benzo[b,d]furan unit for 3aH+. The most stable persistent cations derived from the title compounds, 1-3, were found to be 1aH+ with protonation at C(4), 2aH+ with protonation at C(6), and 3aH+ with protonation at C(6) by experimental and theoretical methods.

A One-Pot Synthesis of Dibenzofurans from 6-Diazo-2-cyclohexenones

A novel and efficient protocol for the rapid construction of dibenzofuran motifs from 6-diazo-2-cyclohexenone and ortho-haloiodobenzene has been developed. The process involves one-pot Pd-catalyzed cross-coupling/aromatization and Cu-catalyzed Ullmann coupling.

A combined experimental and computational study on the cycloisomerization of 2-ethynylbiaryls catalyzed by dicationic arene ruthenium complexes

Ruthenium-catalyzed cycloisomerization of 2-ethynylbiaryls was investigated to identify an optimal ruthenium catalyst system. A combination of [η6-(p-cymene)RuCl2(PR3)] and two equivalents of AgPF6 effectively converted 2-ethynylbiphenyls into phenanthrenes in chlorobenzene at 120 °C over 20 h. Moreover, 2-ethynylheterobiaryls were found to be favorable substrates for this ruthenium catalysis, thus achieving the cycloisomerization of previously unused heterocyclic substrates. Moreover, several control experiments and DFT calculations of model complexes were performed to propose a plausible reaction mechanism.

Experimental NMR and DFT studies of persistent carbocations derived from hetero-polycyclic aromatic hydrocarbons containing oxygen atom: Dibenzo[b,d]furan, Benzo[b]naphtho[1,2-d]furan, Benzo[b]naphtho[2,3-d]furan, Benzo[b]naphtho[2,1-d]furan, and Dinaphtho[2,1-b: 1′,2′-d]furan

Persistent protonation carbocations generated from hetero-PAHs containing oxygen atoms in their aromatic rings, dibenzo[b,d]furan (5), benzo[b]naphtho[1,2-d]furan (6), benzo[b]naphtho[2,3-d]furan (7), benzo[b]naphtho[2,1-d]furan (8), and dinaphtho[2,1-b: 1′,2′-d]furan (9), were directly observed by NMR measurements in superacid. Compound 5 was protonated mainly at C(2) in FSO3H-SbF5 (1: 1) or (4: 1)/SO2ClF, and 6, 8, and 9 were protonated exclusively at C(5) in CF3SO3H or FSO3H/SO2ClF, whereas 7 was protonated at C(6) and C(11) to give two species in FSO3H/SO2ClF. Surprisingly, compound 5 resists protonation in FSO3H/SO2ClF to show NMR spectra corresponding to that of the intact material. Positive charge delocalization mapping for carbocations based on experimental Δδ13C values indicates limited delocalization in these systems. The chemical shifts and charge delocalization modes derived by DFT calculations agreed with the experimental results.

Excited state intramolecular proton transfer (ESIPT) from phenol to carbon in selected phenylnaphthols and naphthylphenols

ESIPT and solvent-assisted ESPT in isomeric phenyl naphthols and naphthyl phenols 5-8 were investigated by preparative photolyses in CH 3CN-D2O, fluorescence spectroscopy, LFP, and ab initio calculations. ESIPT takes place only in 5 (D-exchange Φ = 0.3), whereas 6-8 undergo solvent-assisted PT with much lower efficiencies. The efficiency of the ESIPT and solvent-assisted PT is mainly determined by different populations of the reactive conformers in the ground state and the NEER principle. The D-exchange experiments and calculations using RI-CC2/cc-pVDZ show that 5 in S1 deactivates by direct ESIPT from the OH to the naphthalene position 1 through a conical intersection with S0, delivering QM 14 that was detected by LFP (τ = 26 ± 3 ns). ESIPT to position 3 in 5 is possible but it proceeds from a less-populated conformer and involves an energy barrier on S1. In solvent-assisted PT to naphthalene position 4 in 5, zwitterion 17 is formed, which cyclizes to stable naphthofuran photoproducts 9-12. The regiochemistry of the deuteration in solvent-assisted PT was correlated with the NBO charges of the corresponding phenolates/naphtholates 5--8-. Combined experimental and theoretical data indicate that solvent-assisted PT takes place via a sequential mechanism involving first deprotonation of the phenol/naphthol, followed by the protonation by H 2O in the S1 state of phenolate/naphtholate. The site of protonation by H2O is mostly at the naphthalene α-position.

OXYGENATED FUSED RING DERIVATIVE AND ORGANIC ELECTROLUMINESCENCE ELEMENT CONTAINING THE SAME

An oxygen-containing fused ring derivative represented by the following formula (1) wherein Ar1 is an m-valent fused ring group in which four or more rings including one or more rings selected from a furan ring and a pyran ring are fused and HAr is any of the nitrogen-containing heterocyclic group represented by the following formulas (2) to (5):