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Cationic Chain-Growth Polymerization: Mechanism00:57

Cationic Chain-Growth Polymerization: Mechanism

The cationic polymerization mechanism consists of three steps: initiation, propagation, and termination. In the initiation step of the polymerization process, the π bond of a monomer gets protonated by the Lewis acid catalyst, which is formed from boron trifluoride and water. The protonation of the π bond generates a carbocation stabilized by the electron‐donating group. In the propagation step, the π bond of the second monomer acts as a nucleophile and attacks the generated carbocation,...
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Hydroboration-Oxidation of Alkenes

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.
Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)01:16

Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)

Ring-opening metathesis polymerization or ROMP involves strained cycloalkenes as starting materials. The mechanism of ROMP proceeds by reacting cycloalkene with Grubbs catalyst to give metallacyclobutane intermediate which undergoes a ring-opening reaction to form new carbene. The new carbene reacts with another molecule of cycloalkene. Repetition of these steps leads to the formation of an unsaturated open-chain polymer product. All these steps are reversible, however, relieving the ring...
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The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
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Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.

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Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
09:34

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly

Published on: February 6, 2020

Self-assembled cyclic boron-dipyrrin oligomers.

Chusaku Ikeda1, Tatsuya Nabeshima

  • 1Graduate School of Pure and Applied Sciences, University of Tsukuba, Tsukuba, Ibaraki, 305-8571, Japan.

Chemical Communications (Cambridge, England)
|May 16, 2008
PubMed
Summary

Researchers synthesized novel cyclic boron-dipyrrin oligomers using boron trichloride. These compounds were characterized, and their interactions with alkali metal ions were investigated, revealing new insights into boron-based materials.

Area of Science:

  • Supramolecular Chemistry
  • Organoboron Chemistry

Background:

  • Boron-dipyrrin compounds are versatile building blocks in supramolecular chemistry.
  • Self-assembly of boron-containing macrocycles offers unique structural and electronic properties.

Purpose of the Study:

  • To synthesize and characterize novel self-assembled cyclic boron-dipyrrin oligomers.
  • To investigate the interaction of these oligomers with alkali metal ions.

Main Methods:

  • Synthesis of boron-dipyrrin oligomers via reaction of catecholyldipyrrin with boron trichloride.
  • Characterization using proton nuclear magnetic resonance (1H NMR) spectroscopy.
  • Mass spectrometry analysis using matrix-assisted laser desorption/ionization time-of-flight (MALDI-TOF MS).
  • Structural elucidation via X-ray crystallography.

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  • Binding studies with alkali metal ions.

    • Main Results:

    • Successful synthesis of cyclic boron-dipyrrin oligomers (compounds 3-5).
    • Comprehensive characterization confirming the structures of the synthesized oligomers.
    • Demonstration of specific interactions between oligomer 3 and alkali metal ions.

    Conclusions:

    • The study successfully produced and characterized novel cyclic boron-dipyrrin oligomers.
    • The findings highlight the potential of these boron-dipyrrin structures for ion recognition applications.
    • Further research can explore tuning the macrocyclic structure for selective ion binding.