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Related Concept Videos

Halogens03:01

Halogens

18.9K
Group 17 elements, known as halogens, are nonmetals. At room temperature, fluorine and chlorine are gases, bromine is a liquid, and iodine a solid. Astatine is a highly unstable radioactive element, so currently, most of its properties are unknown due to its short half-life. Tennessine is a synthetic element also predicted to be in this group. 
18.9K
Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

2.9K
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...
2.9K
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

2.9K
Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group...
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Pericyclic Reactions: Introduction01:17

Pericyclic Reactions: Introduction

8.5K
Pericyclic reactions are organic reactions that occur via a concerted mechanism without generating any intermediates. The reactions proceed through the movement of electrons in a closed loop to form a cyclic transition state, where rearrangement of the σ and π bonds yields specific products.
Pericyclic reactions can be classified into three categories: electrocyclic reactions, cycloaddition reactions, and sigmatropic rearrangements. Electrocyclic reactions and sigmatropic...
8.5K
Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

4.2K
Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom,...
4.2K
Frost Circles for Different Conjugated Systems01:18

Frost Circles for Different Conjugated Systems

2.8K
The inscribed polygon method is consistent with Hückel’s 4n + 2 rule and helps to learn whether the given cyclic compound is aromatic or not. The compound is stable and aromatic if every bonding molecular orbital (MO) is completely filled with a pair of electrons. However, if the non-bonding or antibonding orbitals are filled with electrons, the compound is unstable and not aromatic. Consider the Frost circle diagrams for cycloalkenes containing 4 to 8 carbons.
2.8K

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Identifying Per- and Polyfluorinated Chemical Species with a Combined Targeted and Non-Targeted-Screening High-Resolution Mass Spectrometry Workflow
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Identifying Per- and Polyfluorinated Chemical Species with a Combined Targeted and Non-Targeted-Screening High-Resolution Mass Spectrometry Workflow

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Perfluorocycloparaphenylenes.

Hiroki Shudo1, Motonobu Kuwayama2,3, Masafumi Shimasaki4

  • 1Graduate School of Science, Nagoya University, Nagoya, 464-8602, Japan.

Nature Communications
|June 28, 2022
PubMed
Summary
This summary is machine-generated.

Researchers synthesized novel ring-shaped perfluoroarenes, perfluorocycloparaphenylenes (PFCPPs), using nickel complexes. These PFCPPs show potential as electron-accepting materials and in creating unique nanocarbon structures.

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Formulation and Acoustic Modulation of Optically Vaporized Perfluorocarbon Nanodroplets
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Formulation and Acoustic Modulation of Optically Vaporized Perfluorocarbon Nanodroplets

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Synthesis of Cyclic Polymers and Characterization of Their Diffusive Motion in the Melt State at the Single Molecule Level
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Synthesis of Cyclic Polymers and Characterization of Their Diffusive Motion in the Melt State at the Single Molecule Level

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Formulation and Acoustic Modulation of Optically Vaporized Perfluorocarbon Nanodroplets
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Synthesis of Cyclic Polymers and Characterization of Their Diffusive Motion in the Melt State at the Single Molecule Level
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Synthesis of Cyclic Polymers and Characterization of Their Diffusive Motion in the Melt State at the Single Molecule Level

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Area of Science:

  • Materials Science
  • Organic Chemistry
  • Supramolecular Chemistry

Background:

  • Perfluorinated aromatic compounds (perfluoroarenes) are vital in materials science due to their electron affinity.
  • Limited synthetic methods for strained perfluoroarenes restrict structural diversity.

Purpose of the Study:

  • To develop new synthetic routes for highly strained perfluoroarenes.
  • To synthesize and characterize a novel class of ring-shaped perfluoroarenes: perfluorocycloparaphenylenes (PFCPPs).

Main Methods:

  • One-pot synthesis of PFCPPs (n=10, 12, 14, 16) using macrocyclic nickel complexes.
  • Structural determination via X-ray crystallography for PF[n]CPPs (n=10, 12, 14).
  • Photophysical and electrochemical characterization.

Main Results:

  • Successful synthesis of PFCPPs (n=10, 12, 14, 16) without noble metals.
  • X-ray crystallography confirmed tubular alignment in PF[n]CPPs (n=10, 12, 14).
  • PF[n]CPPs (n=10, 12, 14) exhibit wide HOMO-LUMO gaps, high reduction potentials, and low-temperature phosphorescence.

Conclusions:

  • PFCPPs represent a new class of strained, ring-shaped perfluoroarenes.
  • These compounds are promising electron-accepting organic materials.
  • PFCPPs can facilitate the development of novel molecular nanocarbon materials.