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Related Concept Videos

Nomenclature of Alkynes02:39

Nomenclature of Alkynes

18.5K
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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Preparation of Alkynes: Alkylation Reaction02:27

Preparation of Alkynes: Alkylation Reaction

10.3K
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.
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Structure and Physical Properties of Alkynes02:37

Structure and Physical Properties of Alkynes

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Introduction:
In nature, compounds containing both carbon and hydrogen are known as "hydrocarbons". Aliphatic hydrocarbons are compounds whose molecules contain saturated single bonds (i.e., alkanes) or unsaturated double or triple bonds. Alkenes contain carbon–carbon double bonds and have a structural formula CnH2n. Unsaturated hydrocarbons containing carbon–carbon triple bonds are called "alkynes" and are structurally represented by the formula CnH2n-2.
The...
10.8K
Nomenclature of Alkenes02:29

Nomenclature of Alkenes

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The IUPAC naming system for alkenes replaces -an- with -en- in the corresponding parent alkanes. Accordingly, a simple alkene replaces the -ane suffix of the alkane with -ene.
As per the IUPAC rules, the longest carbon chain containing the maximum number of double bonds is identified as the parent chain and is numbered such that the doubly bonded carbon atoms receive the lowest possible numbers. The location of the double bond is indicated by the number of its first carbon atom. In branched...
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Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

7.8K
Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
7.8K
Electrophilic Addition to Alkynes: Halogenation02:38

Electrophilic Addition to Alkynes: Halogenation

8.3K
Introduction
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
8.3K

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Related Experiment Video

Updated: Jul 21, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Published on: June 21, 2017

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Hexakis-TIPS-Alkynylated Nonacenes: Persistent and Processible.

Nico Zeitter1, Nikolai Hippchen1, Anna Weidlich2

  • 1Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|July 25, 2023
PubMed
Summary
This summary is machine-generated.

New stable and soluble nonacenes, featuring triisopropylsilyl(TIPS)-ethynyl groups, show potential for organic electronics. These compounds exhibit ambipolar charge transport in solution-processed transistors.

Keywords:
acenesfield-effect transistorsnonaceneorganic electronicsstabilizationsteric shielding

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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Solid-State Physics

Background:

  • Nonacenes are large polycyclic aromatic hydrocarbons with unique electronic properties.
  • Their inherent instability and poor solubility have limited their practical applications.
  • Developing stable and processable nonacene derivatives is crucial for advancing organic electronics.

Purpose of the Study:

  • To synthesize and characterize novel substituted nonacenes with enhanced stability and solubility.
  • To investigate the structural and electronic properties of these new nonacene compounds.
  • To evaluate the performance of a nonacene derivative in organic electronic devices.

Main Methods:

  • Synthesis of four substituted nonacene derivatives.
  • Characterization using UV-vis and EPR spectroscopy.
  • Structural analysis via X-ray crystallography.
  • Device fabrication and testing of a solution-processed transistor.

Main Results:

  • The synthesized nonacenes possess six strategically placed triisopropylsilyl(TIPS)-ethynyl groups, leading to unprecedented stability and solubility.
  • Compounds are stable for weeks in solid-state and exhibit half-lives of 5-9 hours in dilute solution.
  • X-ray crystallography confirmed the structures of two nonacene derivatives.
  • A nonacene derivative demonstrated ambipolar charge transport in a solution-processed transistor with electron mobility (μe) of 0.007 cm²/Vs and hole mobility (μh) of 0.023 cm²/Vs.

Conclusions:

  • The incorporation of TIPS-ethynyl groups significantly enhances the stability and solubility of nonacenes.
  • These novel nonacenes represent a promising class of materials for organic electronic applications.
  • The demonstrated ambipolar charge transport opens avenues for developing advanced organic semiconductor devices.