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Isomerism in Complexes
Isomers are different chemical species that have the same chemical formula.
Transition metal complexes often exist as geometric isomers, in which the same atoms are connected through the same types of bonds but with differences in their orientation in space. Coordination complexes with two different ligands in the cis and trans positions from a ligand of interest form isomers. For example, the octahedral [Co(NH3)4Cl2]+ ion has two isomers (Figure 1) In the cis...
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In an SN2 reaction, the nucleophilic attack on the substrate and departure of the leaving group occurs simultaneously through a transition state. As the nucleophile approaches the substrate from the back-side, the configuration of the substrate carbon changes from tetrahedral to trigonal bipyramidal and then back to tetrahedral, leading to an inversion in the configuration of the product.
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In this lesson, we delve into the role of ring conformation and its stability, which determines the spatial arrangement and, consequently, the molecular symmetry and stereoisomerism of cyclic compounds. 1,2-Dimethylcyclohexane is used as a case study to evaluate the possible number of stereoisomers. Here, given the multiple (n = 2) chiral centers, there are 2n = 4 possible configurations that lack a plane of symmetry, as the ring skeleton exists in a non-planar chair conformation. In addition,...
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Steric Repulsion Induced Conformational Switch in Supramolecular Structures.

Karolis Norvaiša1, Sophie Maguire1, Claire Donohoe1,2

  • 1School of Chemistry, Chair of Organic Chemistry Trinity Biomedical Sciences Institute Trinity College Dublin, The University of Dublin, 152-160 Pearse Street, D02 R590, Dublin 2, Ireland.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|November 18, 2021
PubMed
Summary
This summary is machine-generated.

Strain engineering in overcrowded porphyrins enables selective atropisomeric conversion. This molecular strain strategy creates tuneable shape-persistent conformations for novel supramolecular nanostructures and materials.

Keywords:
AtropisomersCrystallographyNMRPorphyrinoidsSupramolecular Chemistry

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Area of Science:

  • Supramolecular Chemistry
  • Organic Chemistry
  • Materials Science

Background:

  • Picket-fence systems provide inspiration for rigid molecular architectures.
  • Peripherally overcrowded structures present challenges in controlling conformation.
  • Atropisomerism offers a route to molecular shape diversity.

Purpose of the Study:

  • To develop a strain engineering strategy for selective atropisomeric conversion in porphyrins.
  • To create tuneable, shape-persistent porphyrin conformations.
  • To investigate the formation of supramolecular nanostructures from these conformations.

Main Methods:

  • Utilizing strain to impose intramolecular tension in overcrowded porphyrins.
  • Introducing pivalate units to create a highly strained molecular skeleton.
  • Employing thermal equilibration strategies for atropisomer selective conversion.
  • Characterization using absorption spectroscopy and single crystal X-ray analysis.

Main Results:

  • Achieved tuneable, shape-persistent porphyrin conformations.
  • Formed supramolecular polymers with encapsulated small molecules.
  • Demonstrated selective conversion of abundant atropisomers to minor ones via thermal equilibration.
  • Confirmed severe steric repulsions through spectral and crystallographic data.

Conclusions:

  • Molecular strain engineering is an effective strategy for controlling atropisomerism in overcrowded porphyrins.
  • The resulting porphyrin assemblies exhibit unique supramolecular nanostructures.
  • This approach allows for the design of novel materials with potential applications in molecular encapsulation and recognition.