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Stereoisomerism02:52

Stereoisomerism

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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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The Cope rearrangement is classified as a [3,3] sigmatropic shift in 1,5-dienes, leading to a more stable, isomeric 1,5-diene. The reaction involves a concerted movement of six electrons, four from two π bonds and two from a σ bond, via an energetically favorable chair-like transition state.
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Stereoisomerism of Cyclic Compounds02:33

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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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SN2 Reaction: Stereochemistry02:23

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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.
If the substrate is an achiral molecule at the α-carbon, the inversion of configuration is not...
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Polymer Classification: Stereospecificity01:26

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Polymerization generates chiral centers along the entire backbone of a polymer chain. Accordingly, the stereochemistry of the substituent group has a significant effect on polymer properties. Polymers formed from monosubstituted alkene monomers feature chiral carbons at every alternate position in the polymer backbone. Relative to the predominant orientation of substituents at the adjacent chiral carbons, the polymer can exist in three different configurations: isotactic, syndiotactic, and...
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Factors Affecting Dissolution: Polymorphism, Amorphism and Pseudopolymorphism01:21

Factors Affecting Dissolution: Polymorphism, Amorphism and Pseudopolymorphism

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Polymorphism refers to the existence of a drug substance in multiple crystalline forms, known as polymorphs. Recently, this term has been expanded to include solvates (forms containing a solvent), amorphous forms (non-crystalline forms), and desolvated solvates (forms from which the solvent has been removed).
Some polymorphic crystals possess lower aqueous solubility than their amorphous counterparts, leading to incomplete absorption. For instance, the oral suspension of Chloramphenicol, which...
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Controlling the Size, Shape and Stability of Supramolecular Polymers in Water
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Reversible Supramolecular Polymorphism in Solution and Solid Matrix by Manipulating Sidegroup Conformation.

Saptarshi Datta1, Debangshu Chaudhuri1

  • 1Department of Chemical Sciences, Indian Institute of Science Education and Research (IISER) Kolkata, Mohanpur, 741246, India.

Angewandte Chemie (International Ed. in English)
|February 18, 2022
PubMed
Summary
This summary is machine-generated.

Researchers developed a perylene bisimide molecule that self-assembles into three distinct supramolecular polymorphs. Stimuli like temperature and pH reversibly switch between these forms, enabling tunable material properties.

Keywords:
AzobenzenePerylene BisimideReversible PolymorphismSolvent-Solute InteractionsStimuli Responsiveness

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Area of Science:

  • Materials Science
  • Supramolecular Chemistry
  • Stimuli-Responsive Materials

Background:

  • Supramolecular polymorphism enables stimuli-responsive materials.
  • Achieving controlled self-assembly into specific polymorphs is challenging.
  • Solvent-mediated switching between polymorphs is often impractical.

Purpose of the Study:

  • To design a molecule capable of forming multiple, distinct supramolecular polymorphs.
  • To investigate methods for controlling and reversibly switching between these polymorphs.
  • To explore the role of molecular interactions in dictating self-assembly pathways.

Main Methods:

  • Synthesis of a perylene bisimide molecule featuring a trans-azobenzene sidegroup.
  • Characterization of self-assembled structures using optical absorption and FTIR spectroscopy.
  • Investigation of stimuli-responsive behavior using temperature and pH modulation.

Main Results:

  • The molecule self-assembled into three distinct supramolecular polymorphs with varied colors, morphologies, and packing.
  • Hydrogen-bonding interactions between protic solvents and the azobenzene group's nitrogen atom were crucial.
  • These interactions influenced azobenzene planarity and molecular packing, controlling polymorph formation.
  • Reversible switching between polymorphs was achieved in solution and within a silica-gel matrix using temperature and pH.

Conclusions:

  • A novel perylene bisimide molecule enables the formation of multiple, switchable supramolecular polymorphs.
  • Hydrogen-bonding interactions with protic solvents are key to controlling self-assembly and polymorph selection.
  • Stimuli-responsive switching of polymorphs is feasible using external triggers like temperature and pH.
  • This work provides a pathway for developing tunable, stimuli-responsive materials based on supramolecular assembly.