Related Experiment Video
Updated: Mar 22, 2026
09:35
Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
12.2K
An experimental study on arsoles: structural variation, optical and electronic properties, and emission behavior
Makoto Ishidoshiro1, Hiroaki Imoto, Susumu Tanaka
1Faculty of Molecular Chemistry and Engineering, Graduate School of Science and Technology, Kyoto Institute of Technology, Goshokaido-cho, Matsugasaki, Sakyo-ku, Kyoto 606-8585, Japan. kenaka@kit.ac.jp.
Dalton Transactions (Cambridge, England : 2003)
|April 16, 2016
Summary
Arsoles, arsenic-containing heterocycles, are synthesized safely and show properties similar to phospholes. These functional materials exhibit unique optical, electronic, and mechanochromic characteristics, opening new avenues in materials science.
Area of Science:
- Organometallic Chemistry
- Materials Science
- Heterocyclic Chemistry
Background:
- Conventional arsenic precursors pose synthetic challenges due to volatility.
- Arsoles, arsenic analogs of phospholes, have been theoretically predicted but experimentally underexplored.
- Functional heterocycles are crucial for advanced materials with tailored electronic and optical properties.
Purpose of the Study:
- To develop a safe and efficient synthetic route for 2,5-diarylarsoles.
- To investigate the optical and electronic properties of synthesized arsoles.
- To explore the potential of arsoles as functional materials, comparing them to phospholes.
Main Methods:
- Synthesis of 2,5-diarylarsoles using non-volatile arsenic intermediates.
- Palladium-catalyzed Suzuki-Miyaura coupling for molecular functionalization.
- Characterization of optical properties (emission colors, quantum yields) and electronic properties (frontier orbital energy levels).
Main Results:
- A facile and safe synthetic method for 2,5-diarylarsoles was established.
- Synthesized arsoles exhibit optical and electronic properties comparable to phospholes.
- Arsoles demonstrated mechanochromic behavior, a novel characteristic.
Conclusions:
- Arsoles are intrinsically functional heterocycles with tunable properties.
- The developed synthetic strategy overcomes previous limitations in arsenic heterocycle preparation.
- Arsoles present a promising alternative to phospholes in materials science applications, particularly due to their mechanochromic nature.
More Related Videos
Related Concept Videos
01:14π Electron Effects on Chemical Shift: Aromatic and Antiaromatic Compounds
2.0K
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...
2.0K
01:26Variables Affecting Phosphorescence and Fluorescence
1.8K
Fluorescence and phosphorescence are essential phenomena in fields like analytical chemistry, biological imaging, and materials science, where they detect molecular properties and visualize cellular structures. Understanding the variables that influence these luminescent behaviors is crucial for maximizing accuracy and efficiency in their applications. These variables can broadly be grouped into chemical structure, solvent properties, and external conditions, each playing a distinct role in...
1.8K
01:25Aromatic Compounds: Overview
15.5K
In general, the term ‘aromatic’ indicates a pleasant smell or fragrance from fresh flowers, freshly prepared coffee, etc. In the early history of organic chemistry, many benzene derivatives were isolated from the pleasant odor oils of the plants. For example, vanillin was isolated from the oil of vanilla, methyl salicylate from the oil of wintergreen, and cinnamaldehyde from the oil of cinnamon. They all had a pleasant odor; hence the name aromatic was given.
In 1825, Faraday isolated...
In 1825, Faraday isolated...
15.5K
01:14NMR Spectroscopy of Aromatic Compounds
6.7K
Aromatic compounds can be identified or analyzed using proton NMR and carbon‐13 NMR. Typically, aromatic hydrogens or hydrogens directly bonded to the aromatic rings are strongly deshielded by the aromatic ring current. Therefore, they absorb in the range of 6.5–8.0 ppm in proton NMR spectra. For instance, aromatic hydrogens directly bonded to the benzene ring absorb at 7.3 ppm. However, aromatic hydrogens of larger rings absorb farther upfield or downfield than the ideal range.
6.7K
01:20Criteria for Aromaticity and the Hückel 4n + 2 Rule
14.7K
Like benzene, cyclobutadiene and cyclooctatetraene are cyclic compounds with alternate single and double bonds. However, their chemical behavior differs from benzene, as they are unstable and not aromatic. So, what are the structural characteristics of unsaturated compounds categorized as aromatic?
For the first time, Eric Hückel, a German chemical physicist, derived a set of structural features for a compound to be classified as aromatic. This is now known as Hückel’s rule or the 4n +...
For the first time, Eric Hückel, a German chemical physicist, derived a set of structural features for a compound to be classified as aromatic. This is now known as Hückel’s rule or the 4n +...
14.7K
01:18Aromatic Hydrocarbon Anions: Structural Overview
4.3K
Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
Due to the absence of continuous...
Due to the absence of continuous...
4.3K