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Related Concept Videos

Photochemical Electrocyclic Reactions: Stereochemistry01:26

Photochemical Electrocyclic Reactions: Stereochemistry

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
[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 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.
Variables Affecting Phosphorescence and Fluorescence01:26

Variables Affecting Phosphorescence and Fluorescence

Fluorescence and phosphorescence are essential phenomena in fields like analytical chemistry, biological imaging, and materials science, where they detect molecular properties and visualize cellular structures. Understanding the variables that influence these luminescent behaviors is crucial for maximizing accuracy and efficiency in their applications. These variables can broadly be grouped into chemical structure, solvent properties, and external conditions, each playing a distinct role in...
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.
Chirality at Nitrogen, Phosphorus, and Sulfur02:30

Chirality at Nitrogen, Phosphorus, and Sulfur

Chirality is most prevalent in carbon-based tetrahedral compounds, but this important facet of molecular symmetry extends to sp3-hybridized nitrogen, phosphorus and sulfur centers, including trivalent molecules with lone pairs. Here, the lone pair behaves as a functional group in addition to the other three substituents to form an analogous tetrahedral center that can be chiral.
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...

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Updated: May 31, 2026

Controlling the Size, Shape and Stability of Supramolecular Polymers in Water
16:24

Controlling the Size, Shape and Stability of Supramolecular Polymers in Water

Published on: August 2, 2012

Solvent-Dependent Aggregation, Fluorescence Enhancement, and Supramolecular Chirality Inversion in

Lukang Ji1,2, Jianing Yang1, Shaoxuan Wang1

  • 1Hebei Key Laboratory of Organic Functional Molecules, College of Chemistry and Materials Science, Hebei Normal University, Shijiazhuang, Hebei, China.

Luminescence : the Journal of Biological and Chemical Luminescence
|May 29, 2026
PubMed
Summary

This study shows how a chiral molecule self-assembles in mixed solvents, leading to aggregation-induced emission and changes in chiroptical properties. The findings highlight the link between molecular aggregation, fluorescence, and chirality control.

Keywords:
circular dichroismfluorescence enhancementsolvent‐dependent aggregationsupramolecular chiralitytetraphenylethylene

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Formation of Ordered Biomolecular Structures by the Self-assembly of Short Peptides
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Formation of Ordered Biomolecular Structures by the Self-assembly of Short Peptides

Published on: November 21, 2013

Area of Science:

  • Supramolecular Chemistry
  • Materials Science
  • Organic Chemistry

Background:

  • Controlling both fluorescence and chiroptical properties in a single self-assembly system is highly desirable.
  • Chiral molecules offer unique optical properties that can be modulated by their assembly.
  • Tetraphenylethylene derivatives are known for aggregation-induced emission (AIE).

Purpose of the Study:

  • To investigate the self-assembly behavior of a chiral tetraphenylethylene derivative in mixed solvents.
  • To explore the correlation between aggregation, fluorescence, and chiroptical responses.
  • To understand the solvent-dependent modulation of supramolecular chirality.

Main Methods:

  • Synthesis of a chiral tetraphenylethylene derivative with glutamic acid units.
  • Solvent-dependent self-assembly studies using dimethylformamide/water mixtures.
  • Spectroscopic analysis (fluorescence, circular dichroism, circularly polarized luminescence).
  • Morphological characterization and molecular dynamics simulations.

Main Results:

  • The chiral tetraphenylethylene derivative exhibited aggregation-induced emission with increasing water fraction.
  • Reversal of circular dichroism and circularly polarized luminescence signals were observed, indicating changes in supramolecular chirality.
  • Optical property changes correlated with variations in intermolecular interactions and aggregate packing.
  • Molecular dynamics simulations provided insights into solvent-dependent aggregation and conformational changes.

Conclusions:

  • The study demonstrates a strong correlation between molecular aggregation, fluorescence enhancement, and chiroptical response in the investigated system.
  • Solvent composition effectively controls supramolecular chirality and optical properties in the self-assembled structures.
  • This chiral tetraphenylethylene-based system offers a platform for designing materials with tunable fluorescence and chiroptical characteristics.