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Related Concept Videos

Properties of Organometallic Compounds01:23

Properties of Organometallic Compounds

Organometallic compounds are compounds that contain a carbon–metal bond. Carbon belongs to an organyl group like alkyl, aryl, allyl, or benzyl groups. The metal can be from Group I or Group II of the periodic table, a transition metal, or a semimetal.
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.
Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

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.
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...
Woodward–Hoffmann Selection Rules and Microscopic Reversibility01:34

Woodward–Hoffmann Selection Rules and Microscopic Reversibility

Electrocyclic reactions, cycloadditions, and sigmatropic rearrangements are concerted pericyclic reactions that proceed via a cyclic transition state. These reactions are stereospecific and regioselective. The stereochemistry of the products depends on the symmetry characteristics of the interacting orbitals and the reaction conditions. Accordingly, pericyclic reactions are classified as either symmetry-allowed or symmetry-forbidden. Woodward and Hoffmann presented the selection criteria for...
Pericyclic Reactions: Introduction01:17

Pericyclic Reactions: Introduction

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 rearrangements are...

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Related Experiment Video

Updated: Jun 22, 2026

Light-driven Molecular Motors on Surfaces for Single Molecular Imaging
08:40

Light-driven Molecular Motors on Surfaces for Single Molecular Imaging

Published on: March 13, 2019

Neutral metallacyclic rotors.

Malaichamy Sathiyendiran1, Jing-Yun Wu, Murugesan Velayudham

  • 1Institute of Chemistry, Academia Sinica, Taipei 115, Taiwan.

Chemical Communications (Cambridge, England)
|June 27, 2009
PubMed
Summary

Researchers developed a novel rhenium-based metallacyclic rotor. This molecular rotor, assembled in one step, features a para-phenylene rotor that exhibits rotation in solution.

Area of Science:

  • Organometallic Chemistry
  • Supramolecular Chemistry
  • Materials Science

Background:

  • Molecular machines are crucial for nanotechnology.
  • Developing efficient and stable molecular rotors is an ongoing challenge.
  • Metallacyclic structures offer unique platforms for molecular motion.

Purpose of the Study:

  • To synthesize and characterize a novel neutral rhenium-based metallacyclic rotor.
  • To investigate the rotational dynamics of the para-phenylene rotor within the metallacyclic framework.
  • To demonstrate a facile one-step assembly method for such rotors.

Main Methods:

  • One-step synthesis of the rhenium-based metallacyclic complex.
  • Solution-state Nuclear Magnetic Resonance (NMR) spectroscopy to confirm structure and dynamics.

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  • Variable-temperature NMR studies to analyze the rotation of the para-phenylene unit.

    • Main Results:

    • A neutral Re-based metallacyclic rotor was successfully synthesized.
    • The para-phenylene unit was confirmed to act as a rotor.
    • The rotor was observed to rotate in solution relative to the stator component.
    • The one-step assembly process proved efficient.

    Conclusions:

    • A functional metallacyclic rotor based on rhenium has been prototyped.
    • The study demonstrates the feasibility of one-step synthesis for such molecular rotors.
    • The observed solution-state rotation highlights potential applications in molecular devices.