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Related Concept Videos

[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement01:21

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

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.
Thermal Electrocyclic Reactions: Stereochemistry01:17

Thermal Electrocyclic Reactions: Stereochemistry

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.
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

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.
Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H01:13

meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H

All meta-directing substituents are deactivating groups. These substituents withdraw electrons from the aromatic ring, making the ring less reactive toward electrophilic substitution. For example, the nitration of nitrobenzene is 100,000 times slower than that of benzene because of the deactivating effect of the nitro group. The first step in an electrophilic aromatic substitution is the addition of an electrophile to form a resonance-stabilized carbocation. The energy diagrams for the...

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Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
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Arylboron Tetraphenylethylene-Analog AIEgens Enabling Reversible Closed-Shell/Open-Shell Switching.

Haoyu Gao1, Yan Tang1, Pengchao Liu2

  • 1College of Chemistry and Materials, Henan Agricultural University, Zhengzhou 450002, P. R. China.

Journal of the American Chemical Society
|July 2, 2026
PubMed
Summary
This summary is machine-generated.

Researchers developed new molecules with aggregation-induced emission (AIE) properties. These materials show tunable light emission and can switch electronic states, enabling advanced optical applications.

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Area of Science:

  • Materials Science
  • Organic Chemistry
  • Photophysics

Background:

  • Aggregation-induced emission (AIE) systems face challenges in integrating emission control with reversible electronic switching.
  • Balancing restriction of intramolecular motion (RIM) and spin delocalization is key for advanced AIE functionalities.

Purpose of the Study:

  • To design and investigate arylboron-functionalized tetraphenylethylene-analog molecules for controlled AIE.
  • To explore the RIM-governed AIE mechanism using a rotor-locking strategy.
  • To achieve reversible electronic-state switching for optoelectronic applications.

Main Methods:

  • Synthesis of arylboron-functionalized tetraphenylethylene-analog molecules.
  • Systematic investigation of structure-property relationships.
  • Electrochemical reduction to generate boron-olefin radicals.
  • Characterization of optical and electronic properties.

Main Results:

  • Demonstrated a RIM-governed AIE mechanism via rotor-locking.
  • Achieved pronounced AIE activity and reversible mechano-/piezochromic responses.
  • Generated stable boron-olefin radicals with broadband absorption (visible to NIR-II).
  • Enabled electrochromic switching between closed- and open-shell states with high optical contrast and fast response.

Conclusions:

  • Rotor positioning is crucial for controlling conformational freedom and emission in AIE systems.
  • The developed molecules offer a platform for tunable AIE and reversible electrochromism.
  • Potential applications include smart displays, smart windows, and light-adaptive systems.