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Related Concept Videos

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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Photochemical Electrocyclic Reactions: Stereochemistry01:26

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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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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.
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A Visible-Light-Driven Dithienylethene Derivative Exhibiting Rapid Photocyclization with Near-Quantitative Conversion

Yangyang Wang1, Xinliang Zeng1, Gaoang Wang1

  • 1Luoyang Key Laboratory of Green Synthesis and Photofunctional Materials, College of Food and Drug, and College of Chemistry and Chemical Engineering, Luoyang Normal University, Luoyang 471934, China.

The Journal of Organic Chemistry
|January 6, 2026
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Summary

This study presents a novel dithienylethene (DTE) derivative with enhanced photochromism. The new DTE shows efficient and rapid switching, maintaining performance in various solutions and films for potential optical material applications.

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Photochemistry

Background:

  • Dithienylethene (DTE) derivatives are known for photochromic properties.
  • Achieving high efficiency in visible-light-driven DTEs is challenging due to low reactivity and conversion efficiency.

Purpose of the Study:

  • To design and synthesize a novel DTE derivative with improved photochromic performance.
  • To investigate the photochromic behavior and efficiency of the new DTE derivative in various conditions.

Main Methods:

  • Rational design and synthesis of a novel DTE derivative (compound 3) with an extended π-conjugated system.
  • Photochromic performance evaluation under alternate irradiation with visible light (420 nm and 600 nm).
  • Time-dependent density functional theory (TD-DFT) calculations to support experimental findings.

Main Results:

  • The novel DTE derivative (3) exhibited efficient photochromism in various solvents.
  • Near-quantitative conversion efficiency and rapid photostationary state (PSS) achievement (within 3 s) under 420 nm irradiation.
  • Excellent photoswitching stability was observed in DMSO and nano-aqueous solutions, as well as in PMMA films.

Conclusions:

  • The rationally designed DTE derivative demonstrates significantly enhanced photochromic properties.
  • The extended π-conjugation via an alkene π-bridge is crucial for improved performance.
  • This DTE derivative shows promise for applications in functional optical materials due to its excellent photochromism and fluorescence emission.