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Related Concept Videos

Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

4.1K
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...
4.1K
Cationic Chain-Growth Polymerization: Mechanism00:57

Cationic Chain-Growth Polymerization: Mechanism

3.0K
The cationic polymerization mechanism consists of three steps: initiation, propagation, and termination. In the initiation step of the polymerization process, the π bond of a monomer gets protonated by the Lewis acid catalyst, which is formed from boron trifluoride and water. The protonation of the π bond generates a carbocation stabilized by the electron‐donating group. In the propagation step, the π bond of the second monomer acts as a nucleophile and attacks the...
3.0K
Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

4.1K
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...
4.1K
Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

3.1K
Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
3.1K
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

12.8K
The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
12.8K
Photochemical Electrocyclic Reactions: Stereochemistry01:26

Photochemical Electrocyclic Reactions: Stereochemistry

2.3K
The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
Selection Rules: Photochemical Activation
2.3K

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A two-dimensional conjugated aromatic polymer via C-C coupling reaction.

Wei Liu1,2,3, Xin Luo2, Yang Bao1,2,3

  • 1Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543, Singapore.

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Chemists created a novel crystalline 2D conjugated polymer using solid-state polymerization. This porous material shows promise as an efficient organic anode for sodium-ion batteries.

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Area of Science:

  • Materials Science
  • Polymer Chemistry
  • Nanotechnology

Background:

  • Fabricating crystalline 2D conjugated polymers with defined structures and porosity is synthetically challenging.
  • These materials are desirable due to their unique physical and electronic properties.

Purpose of the Study:

  • To develop a method for synthesizing crystalline 2D conjugated polymers with in-built porosity.
  • To explore the potential of the synthesized polymer as an organic anode material for sodium-ion batteries.

Main Methods:

  • Solid-state polymerization via C-C coupling of tetrabromopolyaromatic monomers.
  • Mechanical exfoliation to produce 1 nm thick lamellar sheets.
  • Gas-sorption measurements to determine pore size.
  • Electrochemical testing as an organic anode in sodium cells.

Main Results:

  • A crystalline 2D conjugated aromatic polymer was successfully synthesized.
  • The polymer exhibits uniform open channels with a dominant pore size of ~0.6 nm.
  • The material demonstrated fast charge/discharge rates, high reversible capacity, and excellent stability in ambient-temperature sodium cells.

Conclusions:

  • The study presents a viable route for fabricating porous crystalline 2D conjugated polymers.
  • The synthesized polymer is a promising candidate for high-performance organic anodes in sodium-ion batteries.