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A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn...
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In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
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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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Dynamic Borate Esterification for Evolved Supramolecular Chirality and Chiral Optics.

Zhuoer Wang1, Changyu Chu1, Aiyou Hao1

  • 1Key Laboratory of Colloid and Interface Chemistry of Ministry of Education, School of Chemistry and Chemical Engineering, Shandong University, Jinan, 250100, P.R. China.

Angewandte Chemie (International Ed. in English)
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PubMed
Summary
This summary is machine-generated.

Researchers developed a new borate esterification reaction to dynamically control supramolecular chirality and chiroptical properties in materials. This method enables tunable circularly polarized luminescence, advancing chiral functional systems.

Keywords:
Borate esterificationSelf‐assemblySupramolecular chiralityTopochemical synthesis

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Area of Science:

  • Supramolecular chemistry
  • Materials science
  • Organic chemistry

Background:

  • Topological reactions in confined environments enable tunable materials.
  • Potential in functional supramolecular and chiral materials is underexplored.

Purpose of the Study:

  • Introduce borate esterification for dynamic modulation of supramolecular chirality.
  • Explore its application in chiral functional systems and tunable luminescence.

Main Methods:

  • Coassembly of pyrene-phenylalanine and catechol-pyrene derivatives.
  • Borate esterification under ambient conditions.
  • Experimental characterization and DFT computations.
  • Introduction of alizarin for CPL transfer.

Main Results:

  • Spontaneous borate esterification induced nanoscale morphological evolution.
  • Achieved dynamic inversion of supramolecular chirality.
  • Identified π-π stacking to CH-π interactions as the driving force.
  • Demonstrated tunable circularly polarized luminescence (CPL) from blue to red.

Conclusions:

  • Borate esterification provides a versatile platform for designing soft materials and chiral systems.
  • This integration of noncovalent assembly and covalent chemistry broadens the scope of chiral luminescent materials.
  • Opens new avenues for applications in functional chiral systems.