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Chirality at Nitrogen, Phosphorus, and Sulfur02:30

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Chirality is most prevalent in carbon-based tetrahedral compounds, but this important facet of molecular symmetry extends to sp3-hybridized nitrogen, phosphorus and sulfur centers, including trivalent molecules with lone pairs. Here, the lone pair behaves as a functional group in addition to the other three substituents to form an analogous tetrahedral center that can be chiral.
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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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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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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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Chirality is a term that describes the lack of mirror symmetry in an object. In other words, chiral objects cannot be superposed on their mirror images. For example, our feet are chiral, as the mirror image of the left foot, the right foot, cannot be superposed on the left foot.
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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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Configurationally Chiral SuFEx-Based Polymers.

Dong-Dong Liang1, Sidharam P Pujari1, Muthusamy Subramaniam1,2

  • 1Laboratory of Organic Chemistry, Wageningen University, Stippeneng 4, 6708WE, Wageningen, The Netherlands.

Angewandte Chemie (International Ed. in English)
|December 17, 2021
PubMed
Summary
This summary is machine-generated.

Researchers developed a new method for creating chiral polymers with backbone chirality using enantiospecific sulfur-fluorine exchange (SuFEx) reactions. This efficient step-growth polymerization yields high-molecular-weight polymers with tunable properties for advanced applications.

Keywords:
Chiral PolymerClick ChemistryEnantiospecificPolysulfonimidatesSuFEx Reaction

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Area of Science:

  • Polymer Chemistry
  • Organic Synthesis
  • Materials Science

Background:

  • Chiral polymers are crucial for bio-inspired applications.
  • Developing efficient synthetic routes for chiral polymers remains a challenge.

Purpose of the Study:

  • To establish a novel method for synthesizing chiral polymers with configurational backbone chirality.
  • To explore the potential of enantiospecific sulfur-fluorine exchange (SuFEx) polymerization.

Main Methods:

  • Utilized enantiospecific sulfur-fluorine exchange (SuFEx) reaction.
  • Employed chiral di-sulfonimidoyl fluorides (di-SFs) and diphenols.
  • Characterized resulting polymers for molecular weight and dispersity.

Main Results:

  • Successfully produced high-molecular-weight polysulfonimidates (MnPS up to 283 kDa, Đ ~ 1.6).
  • Demonstrated that optical activity arises from configurational chirality at sulfur atoms.
  • Confirmed high enantiospecificity (ee > 98%) through degradation studies.

Conclusions:

  • A novel, efficient step-growth polymerization route for chiral polymers with backbone chirality has been developed.
  • This method allows for the synthesis of tailor-made chiral polymers with precisely controlled properties.
  • The polysulfonimidates represent a new class of chiral polymers with significant potential in various applications.