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Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

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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.
Removing one hydrogen from the intervening CH2 group...
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Stereoisomerism of Cyclic Compounds02:33

Stereoisomerism of Cyclic Compounds

9.0K
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,...
9.0K
Stability of Substituted Cyclohexanes02:30

Stability of Substituted Cyclohexanes

12.7K
This lesson discusses the stability of substituted cyclohexanes with a focus on energies of various conformers and the effect of 1,3-diaxial interactions.
The two chair conformations of cyclohexanes undergo rapid interconversion at room temperature. Both forms have identical energies and stabilities, each comprising equal amounts of the equilibrium mixture. Replacing a hydrogen atom with a functional group makes the two conformations energetically non-equivalent.
For example, in...
12.7K
Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

2.1K
Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.
2.1K
Disubstituted Cyclohexanes: cis-trans Isomerism02:37

Disubstituted Cyclohexanes: cis-trans Isomerism

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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....
12.0K
Photochemical Electrocyclic Reactions: Stereochemistry01:26

Photochemical Electrocyclic Reactions: Stereochemistry

1.9K
The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
Selection Rules: Photochemical Activation
1.9K

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Updated: Jul 16, 2025

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
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Cyclohexene-Embedded Dicyanomethylene Merocyanines - Consecutive Three-Component Coupling-Addition Synthesis and

Julian Papadopoulos1, Guido J Reiss2, Bernhard Mayer1

  • 1Institut für Organische Chemie und Makromolekulare Chemie, Heinrich-Heine-Universität Düsseldorf, Universitätsstraße 1, 40225, Düsseldorf, Germany.

Chemistryopen
|September 16, 2023
PubMed
Summary

Researchers developed a new synthesis for cyclohexene-embedded dicyanomethylene merocyanine dyes. These novel dyes exhibit strong light absorption and a delocalized electronic ground state, paving the way for advanced material applications.

Keywords:
DFT calculationsMichael additioncross-couplingmerocyaninesmulticomponent reactions

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Photochemistry

Background:

  • Merocyanine dyes are crucial in various optical and electronic applications.
  • Efficient synthesis of functionalized merocyanines remains a key challenge.

Purpose of the Study:

  • To develop a concise and efficient synthetic route for cyclohexene-embedded dicyanomethylene merocyanines.
  • To characterize the photophysical properties and electronic structure of the synthesized dyes.

Main Methods:

  • Consecutive three-component alkynylation-addition reaction.
  • UV-Vis spectroscopy for absorption coefficient determination.
  • X-ray crystallography for structural analysis.
  • Time-Dependent Density Functional Theory (TDDFT) calculations for electronic structure.

Main Results:

  • A small library of cyclohexene-embedded dicyanomethylene merocyanine dyes was synthesized in moderate to excellent yields.
  • The synthesized dyes exhibit strong absorption coefficients at their longest wavelength absorption bands.
  • Crystal structure analysis revealed small bond length alternations, indicating a highly delocalized electronic ground state.
  • TDDFT calculations confirmed intense HOMO-LUMO transitions responsible for cyanine-like Stokes shifts.

Conclusions:

  • The developed synthetic method provides efficient access to novel merocyanine dyes.
  • The dyes possess favorable photophysical properties due to their delocalized electronic structure.
  • These findings contribute to the design of new materials for optical and electronic devices.