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Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

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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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Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

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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.
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Thermal Electrocyclic Reactions: Stereochemistry01:17

Thermal Electrocyclic Reactions: Stereochemistry

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The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
2.0K
Photochemical Electrocyclic Reactions: Stereochemistry01:26

Photochemical Electrocyclic Reactions: Stereochemistry

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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
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Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)00:53

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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.
Similar to cross-metathesis, ADMET also involves the formation of metallacyclobutane intermediate by [2+2] cycloaddition of one of the double bonds of a terminal diene with...
1.9K
Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

2.6K
Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
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Tuning vibration-induced emission through macrocyclization and catenation.

Wei-Tao Xu1, Zhiyong Peng1, Peicong Wu2

  • 1Shanghai Key Laboratory of Green Chemistry and Chemical Processes, State Key Laboratory of Petroleum Molecular and Process Engineering (SKLPMPE), School of Chemistry and Molecular Engineering, East China Normal University 3663 N. Zhongshan Road Shanghai 200062 China wwang@chem.ecnu.edu.cn.

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Macrocyclization and catenation regulate vibration-induced emission (VIE) in novel luminogens. The [2]catenane structure enables tunable emissions and circularly polarized luminescence, creating smart chiral materials.

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Area of Science:

  • Supramolecular Chemistry
  • Photophysics
  • Materials Science

Background:

  • Vibration-induced emission (VIE) is a photophysical phenomenon sensitive to molecular dynamics.
  • Controlling VIE is crucial for developing advanced luminescent materials.
  • Macrocyclization and catenation offer unique structural frameworks for molecular design.

Purpose of the Study:

  • To investigate the impact of macrocyclization and catenation on vibration-induced emission (VIE).
  • To evaluate the dynamic relaxation processes of novel VIE luminogens based on 9,14-diphenyl-9,14-dihydrodibenzo[a, c]phenazine (DPAC).
  • To explore the potential for tunable emission and circularly polarized luminescence.

Main Methods:

  • Synthesis of macrocyclic and [2]catenane structures incorporating the DPAC luminogen.
  • Femtosecond transient absorption (TA) spectroscopy to probe dynamic relaxation.
  • Viscosity-dependent emission studies in various solvents.
  • Chiroptical characterization of chiral [2]catenanes.

Main Results:

  • The [2]catenane structure significantly influenced the VIE properties.
  • Precisely tunable emissions were achieved by altering solvent viscosity.
  • Chiral [2]catenanes exhibited circularly polarized luminescence.
  • The incorporation of pillar[5]arene introduced planar chirality.

Conclusions:

  • Macrocyclization and catenation are effective strategies for regulating VIE.
  • The [2]catenane framework provides a platform for viscosity-responsive luminescent materials.
  • Chiral [2]catenanes offer a promising route towards smart chiral luminescent materials with tunable properties.