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Isomerism in Alkenes02:01

Isomerism in Alkenes

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Alkenes like 1-butene and 2-butene exhibit constitutional isomerism, as they differ in the position of the double bond. Further, 2-butene exhibits stereoisomerism and exists as two distinct compounds differing in spatial arrangement.
An isomer is called cis-2-butene when the methyl groups are on the same side of the double bond, and the other stereoisomer, in which methyl groups are on the opposite side of the double bond, is called trans-2-butene. The cis and trans stereoisomers are not...
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Stereoisomerism of Cyclic Compounds02:33

Stereoisomerism of Cyclic Compounds

9.2K
In this lesson, we delve into the role of ring conformation and its stability, which determines the spatial arrangement and, consequently, the molecular symmetry and stereoisomerism of cyclic compounds. 1,2-Dimethylcyclohexane is used as a case study to evaluate the possible number of stereoisomers. Here, given the multiple (n = 2) chiral centers, there are 2n = 4 possible configurations that lack a plane of symmetry, as the ring skeleton exists in a non-planar chair conformation. In addition,...
9.2K
Nomenclature of Alkynes02:39

Nomenclature of Alkynes

19.1K
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:
19.1K
Structure and Physical Properties of Alkynes02:37

Structure and Physical Properties of Alkynes

11.4K
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...
11.4K
Constitutional Isomers of Alkanes02:18

Constitutional Isomers of Alkanes

19.1K
Organic compounds of the same molecular formula can have different structural formulas called constitutional isomers, and the phenomenon is known as constitutional isomerism. Alkanes with four or more carbons showing multiple structures with the same molecular formula thereby exhibit constitutional isomerism.
The linear isomer of an alkane is prefixed by the term “n”; hence a linear isomer of pentane is known as n-pentane. Based on the type of branching, some of the...
19.1K
Disubstituted Cyclohexanes: cis-trans Isomerism02:37

Disubstituted Cyclohexanes: cis-trans Isomerism

12.3K
Depending upon the different spatial orientation of the substituents, the disubstituted cycloalkanes exhibit two types of stereoisomers. The cis isomers have the substituents on the same side of the ring, whereas the trans isomers have the substituents on the opposite sides. These stereoisomers exhibit different physical properties and cannot be interconverted without breaking the carbon-carbon bonds.
In cyclohexane, the substituents can occupy different positions generating distinct isomers....
12.3K

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Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
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Linear Nonalternant Isomers of Acenes Fusing Multiple Azulene Units.

Shangshang Wang1,2, Min Tang2, Lin Wu2

  • 1Department of Chemistry, Zhejiang University, Hangzhou, Zhejiang 310027, China.

Angewandte Chemie (International Ed. in English)
|June 14, 2022
PubMed
Summary

Researchers developed a modular synthesis for novel azulene building blocks, creating unique pentacene and hexacene isomers. These compounds show tunable photoelectric properties and enhanced near-infrared fluorescence, opening avenues for advanced materials.

Keywords:
Acid-Responsive LuminescenceAzuleneNonalternant IsomersOrganic ElectronicsPolycyclic Aromatic Hydrocarbons

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Photophysics

Background:

  • Azulene derivatives are promising organic semiconductors.
  • Developing modular synthetic routes for complex polycyclic aromatic hydrocarbons remains a challenge.

Purpose of the Study:

  • To establish a modular synthetic strategy for novel nonalternant pentacene and hexacene isomers based on azulene building blocks.
  • To investigate the impact of constitutional isomerism on the photoelectric properties and fluorescence of these novel fused aromatic systems.

Main Methods:

  • Dehydration condensation of aryl-substituted cyclopentadienes and ortho-haloaryl aldehydes.
  • Palladium-catalyzed C-H coupling for constructing the fused aromatic systems.
  • Spectroscopic and electrochemical characterization to determine photophysical and electronic properties.

Main Results:

  • Successfully synthesized four nonalternant isomers: dibenzo[e,g]azulene, benzo[1,2-f:5,4-f']diazulene, benzo[1,2-f:4,5-f']diazulene, and naphtho[2,3-f:6,7-f']diazulene.
  • Observed narrow band gaps and high stability in the synthesized isomers.
  • Demonstrated protonation-enhanced near-infrared fluorescence.
  • Found that constitutional isomerism significantly influences photoelectric properties, and conjugation length does not always correlate with band gap narrowing.

Conclusions:

  • The developed modular approach provides facile access to diverse multiazulene-fused aromatics.
  • The synthesized isomers possess attractive optoelectronic properties for potential applications in organic electronics.
  • This strategy offers a versatile platform for designing novel functional organic materials with tunable properties.