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Related Concept Videos

Polymer Classification: Stereospecificity01:26

Polymer Classification: Stereospecificity

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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Molecules that possess multiple chiral centers can afford a large number of stereoisomers. For instance, while some molecules like 2-butanol have one chiral center, defined as a tetrahedral carbon atom with four different substituents attached, several molecules like butane-2,3-diol have multiple chiral centers. A simple formula to predict the number of stereoisomers possible for a molecule with n chiral centers is 2n. However, there can be a lower number where some of the stereoisomers are...
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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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The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...
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Learning to draw Fischer projections of molecules and understanding their relevance plays a crucial role in the visual depiction of organic molecules. A Fischer projection is a two-dimensional projection on a planar surface to simplify the three-dimensional wedge–dash representation of molecules. This is especially helpful in the case of molecules with multiple chiral centers that can be difficult to draw. Here, all the bonds of interest are represented as horizontal or vertical lines. While...

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Related Experiment Video

Updated: Jul 7, 2026

Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
06:31

Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators

Published on: November 27, 2015

New dicholesteryl-based gelators: chirality and spacer length effect.

Junxia Peng1, Kaiqiang Liu, Jing Liu

  • 1Key Laboratory of Applied Surface and Colloid Chemistry of Ministry of Education, School of Chemistry and Materials Science, Shaanxi Normal University, Xi'an 710062, PR China.

Langmuir : the ACS Journal of Surfaces and Colloids
|February 26, 2008
PubMed
Summary

Chirality and spacer length significantly impact gelation behavior in new dicholesteryl alaninate amides. Specific molecular designs enable spontaneous gel formation and tunable rheological properties.

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Published on: April 16, 2018

Area of Science:

  • Supramolecular Chemistry
  • Materials Science
  • Organic Chemistry

Background:

  • Cholesteryl derivatives are known for their self-assembly properties.
  • Alanine-based molecules offer chiral building blocks for supramolecular structures.
  • Controlling gelation behavior is crucial for developing novel functional materials.

Purpose of the Study:

  • To synthesize and characterize novel diacid amides of dicholesteryl L(D)-alaninates.
  • To investigate the influence of spacer length and amino acid chirality on gelation properties.
  • To explore the potential of these compounds as gelators for various applications.

Main Methods:

  • Synthesis of eight new diacid amides.
  • Gelation tests to assess gel-forming ability.
  • Scanning Electron Microscopy (SEM), X-ray Diffraction (XRD), and Circular Dichroism (CD) for microstructure analysis.
  • Rheological studies to evaluate mechanical properties and thixotropy.

Main Results:

  • Spacer length and chirality dramatically affect gelation behavior and microstructure.
  • Compounds with shorter spacers (1, 2) showed enhanced gelation with D-alanine residues.
  • Compounds with longer spacers (3, 4) exhibited superior gelation with L-alanine residues.
  • Eleven out of 139 systems spontaneously gelled at room temperature.
  • Rheological studies revealed significant effects of spacer length on mechanical properties and thixotropic behavior.
  • One compound (4a) formed water-in-oil gel emulsions.

Conclusions:

  • Molecular design, specifically spacer length and chirality, is critical for controlling self-assembly and gelation.
  • These novel compounds demonstrate potential as efficient gelators with tunable properties.
  • The formation of spontaneous gels and gel emulsions highlights their versatility for materials applications.