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Related Concept Videos

Preparation of Alkynes: Alkylation Reaction02:27

Preparation of Alkynes: Alkylation Reaction

Introduction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
Free-Radical Chain Reaction and Polymerization of Alkenes02:35

Free-Radical Chain Reaction and Polymerization of Alkenes

The conversion of alkenes to macromolecules called polymers is a reaction of high commercial importance. The structure of the polymer is defined by a repeating unit, while the terminal groups are considered insignificant. The average degree of polymerization represents the number of repeating units in the polymer molecule and is denoted by the subscript n.
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

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.
Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)00:53

Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)

Acyclic diene metathesis polymerization or ADMET polymerization involves cross-metathesis of terminal dienes, such as 1,8-nonadiene, to give linear unsaturated polymer and ethylene. As ADMET is a reversible process, the formed ethylene gas must be removed from the reaction mixture to complete the polymerization process.
Similar to cross-metathesis, ADMET also involves the formation of metallacyclobutane intermediate by [2+2] cycloaddition of one of the double bonds of a terminal diene with...
Radical Chain-Growth Polymerization: Chain Branching01:17

Radical Chain-Growth Polymerization: Chain Branching

The skeletal structure of polymers synthesized via radical polymerization is always branched. For example, the polymerization of ethylene by radical polymerization results in a low-density grade of polyethylene with a heavily branched skeletal structure. Here, the radical site abstracts hydrogen from the growing chain, and the radical site shifts from the end (a primary carbon center) to anywhere within the growing chain (a secondary carbon center). Consequently, the part of the chain from the...
Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene01:14

Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene

Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.

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Acetylene-expanded dendralene segments with exotopic phosphaalkene units.

Xue-Li Geng1, Sascha Ott

  • 1Department of Photochemistry and Molecular Science, Ångström Laboratories, Uppsala University, Regementsvagen 1, Box 523, 75120 Uppsala, Sweden.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|September 15, 2011
PubMed
Summary

This study introduces a novel building block, bis-TMS protected C,C-diacetylenic phosphaalkene (A(2)PA), for creating extended conjugated systems. Controlled coupling reactions enable the synthesis of new materials with tunable electronic properties due to phosphorus centers.

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Area of Science:

  • Organophosphorus Chemistry
  • Materials Science
  • Organic Synthesis

Background:

  • Phosphaalkenes are versatile building blocks in synthesis.
  • Expansion of π-conjugated systems is crucial for advanced materials.
  • Controlled functionalization of diyne units is synthetically challenging.

Purpose of the Study:

  • To synthesize butadiyne-expanded dendralene fragments using a novel phosphaalkene.
  • To explore controlled homo- and heterocoupling reactions of the phosphaalkene.
  • To investigate the electronic properties and structural integrity of the resulting compounds.

Main Methods:

  • Synthesis of bis-TMS protected C,C-diacetylenic phosphaalkene (A(2)PA) 1.
  • Copper- and palladium-catalyzed oxidative acetylene coupling reactions.
  • Crystallographic characterization and spectroscopic analysis (UV/Vis, electrochemical).

Main Results:

  • Selective functionalization of the acetylene termini of A(2)PA 1 was achieved.
  • Stereochemistry across the P=C bond was conserved during coupling reactions.
  • Efficient π-conjugation was observed throughout the acetylenic framework, with tunable electronic properties influenced by substituents.

Conclusions:

  • A(2)PA 1 is a valuable building block for constructing extended conjugated systems.
  • The phosphorus centers significantly influence the electronic properties, leading to smaller HOMO-LUMO gaps.
  • Substituent-controlled tuning of frontier molecular orbitals is feasible for designing novel materials.