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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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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.
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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.
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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.
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Chain-growth or addition polymerization is successive addition reactions of monomers with a polymer chain. In radical chain-growth polymerization, the reaction proceeds via a free-radical intermediate. The free radical is formed from radical initiators, which spontaneously generate free radicals by homolytic fission. Organic peroxides (such as dibenzoyl peroxide, as shown in Figure 1) or azo compounds are popular radical initiators. A low concentration ratio of radical initiator to monomer is...
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Flexible Organic Radical Cocrystal With 94% Photothermal Conversion Efficiency.

Bingrui Chen1, Huixu Yang1, Siqi Zhang1

  • 1Department of Chemistry, Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, Zhejiang Normal University, Jinhua, China.

Angewandte Chemie (International Ed. in English)
|April 22, 2026
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Summary
This summary is machine-generated.

Researchers developed flexible organic crystals for efficient photothermal energy conversion. These novel materials overcome limitations of traditional composites, offering stable and high-performance solar energy harvesting.

Keywords:
charge transferflexibilityorganic cocrystalphotothermal conversionradical

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Area of Science:

  • Materials Science
  • Organic Electronics
  • Photothermal Conversion

Background:

  • Flexible photothermal materials often face interfacial incompatibility issues, leading to poor long-term stability and performance.
  • Existing composite materials struggle to balance interfacial stability with high photothermal efficiency.

Purpose of the Study:

  • To develop a novel flexible photothermal material with enhanced interfacial stability and high performance.
  • To explore the potential of flexible organic crystals for efficient solar energy harvesting.

Main Methods:

  • Cocrystallization of electron donor perylene (PE) and acceptor naphthalene diimide (NDI) to form flexible PE-NDI organic crystals.
  • Characterization of radical characteristics, light absorption, mechanical properties, and photothermal conversion efficiency.
  • Integration into a thermoelectric generator for photo-thermo-electric conversion.

Main Results:

  • Achieved centimeter-size, mechanically flexible PE-NDI cocrystals with persistent radical characteristics (2.1 µs spin coherence time).
  • Demonstrated strong light absorption (200-780 nm) due to prominent donor-acceptor interaction (-87.7 kJ mol⁻¹).
  • Obtained an exceptionally high photothermal conversion efficiency of 94% at 685 nm excitation and observed reversible elastic bending.

Conclusions:

  • Flexible organic crystals, specifically PE-NDI cocrystals, offer a promising single-component solution for stable and efficient photothermal materials.
  • These materials enable direct solar energy harvesting through photo-thermo-electric conversion, highlighting their potential in renewable energy applications.
  • The study underscores the untapped potential of mechanically compliant organic crystals for lightweight, high-performance photothermal applications.