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Cationic Chain-Growth Polymerization: Mechanism00:57

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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...
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The word polymer is derived from the Greek words “poly” which means “many” and “mer” which means “parts”. Polymers are long chains of molecules composed of repeating units of smaller molecules, known as monomers. They either occur naturally, such as DNA and proteins, or can be constructed synthetically, like plastics. They have varied structural characteristics, such as linear chains, branched chains, or complex networks, that contribute to the...
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Step-Growth Polymerization: Overview01:03

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Step-growth or condensation polymerization is a stepwise reaction of bi or multifunctional monomers to form long-chain polymers. As all the monomers are reactive, most of the monomers are consumed at the early stages of the reaction to form small chains of reactive oligomers, which then combine to form long polymer chains in the late stages. Hence, the reaction has to proceed for a long time to achieve high molecular weight polymers.
Many natural and synthetic polymers are produced by...
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Anionic Chain-Growth Polymerization: Mechanism01:04

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The mechanism for anionic chain-growth polymerization involves initiation, propagation, and termination steps. In the initiation step, a nucleophilic anion, such as butyl lithium, initiates the polymerization process by attacking the π bond of the vinylic monomer. As a result, a carbanion, stabilized by the electron‐withdrawing group, is generated. The resulting carbanion acts as a Michael donor in the propagation step and attacks the second vinylic monomer, which acts as a Michael...
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The polymerization process that involves carbanion as an intermediate is called anionic polymerization. It is also a type of addition or chain-growth polymerization. Anionic polymerization gets initiated by a strong nucleophile such as an organolithium or a Grignard reagent. The most commonly used initiator for anionic polymerization is butyl lithium. Monomers involved in anionic polymerization must possess a vinyl group bonded to one or two electron-withdrawing groups. For instance,...
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Phosphodiester bond forms when a phosphoric acid molecule (H3PO4) links with two hydroxyl groups (–OH) of two other molecules, forming two ester bonds. Two water molecules are released in this process. The phosphodiester bond is commonly found in nucleic acids (DNA and RNA) and plays a critical role in their structure and function.
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Depolymerization of Poly(phosphinoboranes): From Polymers to Lewis Base Stabilized Monomers.

Christian Marquardt1, Oliver Hegen1, Ariane Vogel1

  • 1Institut für Anorganische Chemie, Universität Regensburg, 93040, Regensburg, Germany.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|November 23, 2017
PubMed
Summary

Poly(phosphinoboranes) undergo depolymerization when treated with strong Lewis bases, specifically N-heterocyclic carbenes. This reaction yields monomeric phosphanylboranes, with efficiency dependent on Lewis base strength and polymer structure.

Keywords:
Lewis basesboranescarbenescleavage reactionsphosphorus

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Area of Science:

  • Polymer Chemistry
  • Organometallic Chemistry
  • Materials Science

Background:

  • Poly(phosphinoboranes) are polymers with a unique backbone structure.
  • Understanding their reactivity, particularly depolymerization, is crucial for potential applications.
  • Lewis bases, especially N-heterocyclic carbenes (NHCs), are known to interact with various chemical species.

Purpose of the Study:

  • To investigate the depolymerization reactions of poly(phosphinoboranes) using strong Lewis bases.
  • To identify the factors influencing the depolymerization process.
  • To characterize the resulting monomeric phosphanylboranes.

Main Methods:

  • Depolymerization reactions of poly(phosphinoboranes) with Lewis bases (LBs), including NHCs.
  • Structural determination of monomeric phosphanylboranes using X-ray crystallography.
  • Density Functional Theory (DFT) calculations to support experimental observations.

Main Results:

  • Cleavage of poly(phosphinoboranes) [H2PBH2]n, [tBuHPBH2]n, [PhHPBH2]n, and [Ph2PBH2]n was achieved using strong LBs.
  • Monomeric phosphanylboranes (R1R2PBH2LB) were successfully synthesized.
  • Depolymerization efficiency was found to correlate with LB strength and stability, and the polymer's substitution pattern.
  • Solid-state structures of H2PBH2NHCMe, H2PBH2NHCdipp, and tBuHPBH2NHCMe were determined.

Conclusions:

  • Strong Lewis bases, particularly NHCs, effectively depolymerize poly(phosphinoboranes).
  • The reaction outcome is tunable by modifying the Lewis base and the phosphinoborane structure.
  • Experimental findings are corroborated by DFT calculations, providing a deeper mechanistic understanding.