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Related Concept Videos

Chair Conformation of Cyclohexane02:02

Chair Conformation of Cyclohexane

The chair conformation is the most stable form of cyclohexane due to the absence of angle and torsional strain. The absence of angle strain is a result of cyclohexane’s bond angle being very close to the ideal tetrahedral bond angle of 109.5° in its chair conformer. Similarly, the torsional strain is also absent owing to the perfectly staggered arrangement of bonds.
The hydrogen atoms linked to carbons are arranged in two different axial and equatorial orientations to achieve this staggered...
Conformations of Cyclohexane02:11

Conformations of Cyclohexane

Cyclohexane does not exist in a planar form due to the high angle and torsional strain it would experience in the planar structure. Instead, it adopts non-planar chair and boat conformations.
The chair form is the most stable and derives its name from its resemblance to the “easy chair.” In the chair conformation, two carbon atoms are arranged out-of-plane — one above and one below, minimizing the torsional strain. In the chair form, the bond angle is very close to the ideal tetrahedral value,...
Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)01:16

Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)

Ring-opening metathesis polymerization or ROMP involves strained cycloalkenes as starting materials. The mechanism of ROMP proceeds by reacting cycloalkene with Grubbs catalyst to give metallacyclobutane intermediate which undergoes a ring-opening reaction to form new carbene. The new carbene reacts with another molecule of cycloalkene. Repetition of these steps leads to the formation of an unsaturated open-chain polymer product. All these steps are reversible, however, relieving the ring...
Thermal Electrocyclic Reactions: Stereochemistry01:17

Thermal Electrocyclic Reactions: Stereochemistry

The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

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 with both...
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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

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.

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Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
09:35

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Published on: September 18, 2016

Copper(I)-assembled [3]rotaxane whose two rings act as flapping wings.

Antoine Joosten1, Yann Trolez, Jean-Paul Collin

  • 1Laboratoire de Chimie Organo-Minérale, Institut de Chimie, Université de Strasbourg-CNRS/UMR7177, 4 rue Blaise Pascal, 67070 Strasbourg Cedex, France.

Journal of the American Chemical Society
|January 13, 2012
PubMed
Summary

Researchers developed a novel copper-complexed [3]rotaxane using click chemistry. This molecular machine exhibits a unique "wing-flapping" motion triggered by metal coordination changes, paving the way for new functional molecular machines.

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Self-assembling Morphologies Obtained from Helical Polycarbodiimide Copolymers and Their Triazole Derivatives
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Self-assembling Morphologies Obtained from Helical Polycarbodiimide Copolymers and Their Triazole Derivatives

Published on: February 7, 2017

Area of Science:

  • Supramolecular Chemistry
  • Coordination Chemistry
  • Materials Science

Background:

  • Rotaxanes are mechanically interlocked molecules with potential applications in molecular machines.
  • The incorporation of metal centers can introduce dynamic and responsive behaviors into rotaxane systems.
  • Click chemistry offers efficient and reliable methods for constructing complex molecular architectures.

Purpose of the Study:

  • To synthesize a novel copper-complexed [3]rotaxane with switchable coordination environments.
  • To investigate the influence of metal coordination on the rotaxane's geometry and dynamics.
  • To explore the potential of this system as a functional molecular machine.

Main Methods:

  • Synthesis of a [3]rotaxane using click chemistry for stoppering.
  • Complexation with different metal ions (Cu(I), Cu(II), Zn(2+)).
  • Spectroscopic and structural analysis to determine coordination modes and geometry.

Main Results:

  • A new copper-complexed [3]rotaxane was successfully synthesized.
  • The triazole groups in the rotaxane can either coordinate to or remain outside the metal's coordination sphere.
  • Metal exchange (Cu(I)/Zn(2+)) or redox processes (Cu(II)/Cu(I)) induce significant geometrical changes, leading to a "wing-flapping" motion.

Conclusions:

  • The synthesized rotaxane exhibits controllable dynamic behavior based on metal coordination.
  • The observed "wing-flapping" motion is fast and quantitative.
  • This system holds promise for the development of advanced molecular machines and responsive materials.