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Related Concept Videos

NMR Spectroscopy of Benzene Derivatives01:34

NMR Spectroscopy of Benzene Derivatives

11.0K
Simple unsubstituted benzene has six aromatic protons, all chemically equivalent. Therefore, benzene exhibits only a singlet peak at δ 7.3 ppm in the 1H NMR spectrum. The observed shift is far downfield because the aromatic ring current strongly deshields the protons. Any substitution on the benzene ring makes the aromatic protons nonequivalent, and the protons split each other. The peak is, therefore, no longer a singlet and the splitting pattern and their associated coupling...
11.0K
Hydrolysis of Chlorobenzene to Phenol: Dow Process01:10

Hydrolysis of Chlorobenzene to Phenol: Dow Process

3.9K
Simple aryl halides do not react with nucleophiles under normal conditions. However, the reaction can proceed under drastic conditions involving high temperatures and high pressure to give the substituted products. For example, chlorobenzene is converted to phenol using aqueous sodium hydroxide at 350 °C under high pressure by the Dow process. The reaction follows an elimination-addition mechanism involving a benzyne intermediate. Here, the chloride ion is...
3.9K
Structure of Benzene: Molecular Orbital Model01:18

Structure of Benzene: Molecular Orbital Model

12.1K
According to the molecular orbital (MO) model, benzene has a planar structure with a regular hexagon of six sp2 hybridized carbons. As shown in Figure 1, each carbon is bonded to three other atoms with C–C–C and H–C–C bond angles of 120°. The C–H bond length is 109 pm, and the C–C bond length is 139 pm which is midway between the single bond length of sp3 hybridized carbons (154 pm) and sp2 hybridized carbons (133 pm).
12.1K
π Electron Effects on Chemical Shift: Aromatic and Antiaromatic Compounds01:14

π Electron Effects on Chemical Shift: Aromatic and Antiaromatic Compounds

1.8K
In aromatic compounds, such as benzene, the circulation of (4n + 2) π-electrons sets up a diamagnetic or diatropic ring current around the perimeter of the molecule. This current induces a magnetic field that opposes the external field inside the ring and reinforces it on the outside. The protons in benzene are deshielded and exhibit high chemical shifts in the range 6.5–8.5 ppm. The shielding effect at the center of the ring is evident in complex aromatic molecules, such as...
1.8K
¹H NMR: Long-Range Coupling01:27

¹H NMR: Long-Range Coupling

2.6K
The coupling interactions of nuclei across four or more bonds are usually weak, with J values less than 1 Hz. While these are usually not observed in spectra, the presence of multiple bonds along the coupling pathway can result in observable long-range coupling.
In alkenes, spin information is communicated via σ–π overlap, as seen in allylic (four-bond) and homoallylic (five-bond) couplings. These coupling interactions are stronger when the σ bond is parallel to the alkene...
2.6K
Benzene to Phenol via Cumene: Hock Process01:27

Benzene to Phenol via Cumene: Hock Process

4.1K
The synthesis of phenol from benzene via cumene and cumene hydroperoxide is called the Hock process. First, a Friedel–Crafts alkylation reaction of benzene with propene gives cumene. Then cumene forms cumene hydroperoxide via a radical chain reaction. In the chain initiation step, the benzylic hydrogen is abstracted to give a benzylic radical. In the chain propagation step, the benzylic radical reacts with an oxygen diradical to form a cumene hydroperoxide radical. The cumene...
4.1K

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Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid
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Benzo-Extended [n]Phenacenes: e‑Flow Synthesis and Length-Dependent Properties.

Qiang Wang1, Wei-Zhen Wang1, Ruiying Zhang1

  • 1Key Laboratory of Molecule Synthesis and Function Discovery (Fujian Province University), College of Chemistry, Fuzhou University, Fuzhou 350108, China.

JACS Au
|September 26, 2025
PubMed
Summary
This summary is machine-generated.

Researchers developed a green synthesis for twisted benzo-extended [n]-phenacenes using an electrochemical flow Scholl reaction. This method efficiently produces polycyclic aromatic hydrocarbons with tunable optical bandgaps for organic electronics.

Keywords:
Continuous flowGNRsScholl reactionelectrosynthesisphenacene

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Electrochemistry

Background:

  • Polycyclic aromatic hydrocarbons (PAHs) are crucial in organic electronics.
  • Developing efficient and sustainable synthetic routes for complex PAHs like benzo-extended [n]-phenacenes ([n]-BPs) remains a challenge.
  • Tuning the electronic properties of PAHs is essential for optimizing device performance.

Purpose of the Study:

  • To develop an efficient, green, and scalable synthetic strategy for twisted benzo-extended [n]-phenacenes ([n]-BPs).
  • To investigate the impact of molecular length on the photophysical properties of [n]-BPs.
  • To enable facile bandgap modulation for potential applications in organic semiconductor devices.

Main Methods:

  • A one-pot three-component Suzuki-Miyaura coupling reaction to synthesize [n]-BP precursors.
  • An electrochemical flow (e-flow) Scholl reaction for the efficient synthesis of twisted [n]-BPs.
  • Characterization of the synthesized [n]-BPs and their photophysical properties.

Main Results:

  • Successful synthesis of diverse twisted [n]-BPs via a green and sustainable e-flow Scholl reaction.
  • The e-flow Scholl reaction demonstrated reduced oxidant usage and overoxidation byproducts.
  • An increase in molecular length of [n]-BPs led to a decrease in the optical bandgap, tuning photophysical properties.
  • The method allows for easy scale-up through extended electrolysis time.

Conclusions:

  • The developed e-flow Scholl reaction provides an efficient and sustainable route to complex [n]-BPs.
  • The synthetic strategy enables facile bandgap modulation via π-conjugation extension.
  • [n]-BPs synthesized through this method show potential for applications in organic semiconductor devices.