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Nomenclature of Alkynes02:39

Nomenclature of Alkynes

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Alkynes are unsaturated hydrocarbons characterized by the presence of carbon-carbon triple bonds and have a general formula CnH2n-2. The nomenclature of alkynes follows a set of rules similar to alkanes and alkenes; however, alkynes bear the suffix "-yne" instead of "-ane" or "-ene." There are two approaches to naming alkynes:
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Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
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Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
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Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
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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.
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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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Synthesis of Cyclic Polymers and Characterization of Their Diffusive Motion in the Melt State at the Single Molecule Level
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Cyclic polyacetylene.

Zhihui Miao1,2, Stella A Gonsales1, Christian Ehm3

  • 1Department of Chemistry, University of Florida, Center for Catalysis, Gainesville, FL, USA.

Nature Chemistry
|June 4, 2021
PubMed
Summary

We synthesized cyclic polyacetylene ([∞]annulene) using tungsten catalysis. This novel cyclic polymer exhibits high trans double bond content and conductivity, opening new avenues for polymer derivatization and applications.

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Area of Science:

  • Polymer Chemistry
  • Organic Synthesis
  • Materials Science

Background:

  • Traditional synthesis of polyacetylene yields linear chains.
  • Controlling the topology of polymers is crucial for their properties.
  • Cyclic polymers offer unique structural and electronic characteristics.

Purpose of the Study:

  • To demonstrate the synthesis of cyclic polyacetylene ([∞]annulene).
  • To characterize the topological and electronic properties of cyclic polyacetylene.
  • To explore potential applications of this novel cyclic polymer.

Main Methods:

  • Homogeneous tungsten-catalyzed polymerization of acetylene.
  • Atomic force microscopy (AFM) for topological analysis.
  • Electrical conductivity measurements of doped cyclic polyacetylene.

Main Results:

  • Successful synthesis of cyclic polyacetylene (>99% trans double bonds) via acetylene polymerization.
  • Demonstration of temporarily soluble cyclic polyacetylene for solution derivatization.
  • AFM imaging confirmed cyclic topology through bottlebrush derivatives.
  • Doped cyclic polyacetylene films exhibited high electrical conductivity (398 Ω⁻¹cm⁻¹).

Conclusions:

  • Cyclic polyacetylene can be efficiently synthesized using tungsten catalysis.
  • The cyclic structure imparts unique properties, including high isomer purity and conductivity.
  • This work enables new possibilities for functionalizing and utilizing cyclic conjugated polymers.