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Stability of Conjugated Dienes01:28

Stability of Conjugated Dienes

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Introduction
A comparison of the enthalpies of hydrogenation of dienes reveals that conjugated dienes release less heat on hydrogenation, rendering them more stable than their nonconjugated analogs.
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The Diels–Alder reaction brings together a diene and a dienophile to form a six-membered ring. Both components have unique characteristics that influence the rate of the reaction.
Characteristics of the diene
Conformation
The simplest example of a diene is 1,3-butadiene, an acyclic conjugated π system. At room temperature, the molecule exists as a mixture of s-cis and s-trans conformers by virtue of rotation around the carbon–carbon single bond. Although the s-trans isomer is more stable,...
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[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement01:21

[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement

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The Cope rearrangement is classified as a [3,3] sigmatropic shift in 1,5-dienes, leading to a more stable, isomeric 1,5-diene. The reaction involves a concerted movement of six electrons, four from two π bonds and two from a σ bond, via an energetically favorable chair-like transition state.
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Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
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Relative Stabilities of Alkenes01:59

Relative Stabilities of Alkenes

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The relative stability of alkenes can be determined by comparing their heats of hydrogenation. The lower heat of hydrogenation indicates the more stable alkene.  The three main factors determining the relative stability of alkenes are i) the number of substituents attached to the double-bond carbon atoms, ii) hyperconjugation, and iii) the stereochemistry of the double bond.
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Isomerism in Alkenes02:01

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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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A stable AIEgen cis-diarylethene-based 'ESIPT' benchmark.

Tingting Zhang1, Liu Wen1, Genjiang Liu1

  • 1College of Materials and Chemical Engineering, Key Laboratory of Inorganic Nonmetallic Crystalline and Energy Conversion Materials, China Three Gorges University, Yichang 443002, Hubei, P. R. China. yanjiaying327@126.com nnzhang2015@ctgu.edu.cn.

Chemical Communications (Cambridge, England)
|October 29, 2019
PubMed
Summary

Researchers developed a one-flask synthesis for novel seven-membered free-base BOPYINs (NBs). These molecules exhibit stable cis-configuration and Aggregation Induced Emission (AIE) due to hydrogen bonding and steric hindrance, enabling Excited-State Intramolecular Proton Transfer (ESIPT) phenomena.

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Photophysics

Background:

  • Diarylethenes are known for their photochromic properties and potential in molecular switches.
  • Aggregation-Induced Emission (AIE) is a phenomenon where molecules exhibit luminescence only when aggregated.
  • Excited-State Intramolecular Proton Transfer (ESIPT) is a key photophysical process influencing molecular fluorescence.

Purpose of the Study:

  • To report a novel one-flask synthesis of seven-membered free-base BOPYINs (NBs).
  • To investigate the structural and photophysical properties of these newly synthesized NBs.
  • To explore the potential of these NBs in applications requiring AIE and ESIPT phenomena.

Main Methods:

  • One-flask synthesis utilizing benzo indole and β-substituted pyrrole moieties.
  • Structural characterization using spectroscopic and crystallographic techniques.
  • Photophysical studies to evaluate Aggregation Induced Emission (AIE) and Excited-State Intramolecular Proton Transfer (ESIPT) properties.

Main Results:

  • Successful synthesis of seven-membered free-base BOPYINs (NBs) in a single flask.
  • Demonstration of a stable cis-configuration locked by intramolecular hydrogen bonding and steric hindrance.
  • Observation of significant Aggregation Induced Emission (AIE) properties.
  • Confirmation of Excited-State Intramolecular Proton Transfer (ESIPT) phenomena in these diarylethenes.

Conclusions:

  • The developed one-flask synthesis provides efficient access to novel seven-membered BOPYINs.
  • The unique structural features enable stable AIE and ESIPT, making them promising for advanced materials.
  • These findings contribute to the understanding of structure-property relationships in diarylethene-based AIEgens.