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Related Concept Videos

Preparation and Reactions of Thiols02:33

Preparation and Reactions of Thiols

6.7K
Thiols are prepared using the hydrosulfide anion as a nucleophile in a nucleophilic substitution reaction with alkyl halides. For instance, bromobutane reacts with sodium hydrosulfide to give butanethiol.
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[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

8.0K
The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
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Structure of Conjugated Dienes01:16

Structure of Conjugated Dienes

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Introduction
Conjugated dienes are compounds characterized by the presence of alternating double and single bonds. In a conjugated system like 1,3-butadiene, the unhybridized 2p orbital on each carbon overlaps continuously, allowing the π electrons to be delocalized across the entire molecule. In contrast, this type of overlap does not occur in cumulated and isolated dienes, such as 2,3-pentadiene and 1,4-pentadiene, respectively. Instead, the π electrons remain localized between the...
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Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

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Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
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Stability of Conjugated Dienes01:28

Stability of Conjugated Dienes

3.4K
Introduction
A comparison of the enthalpies of hydrogenation of dienes reveals that conjugated dienes release less heat on hydrogenation, rendering them more stable than their nonconjugated analogs.
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Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene01:14

Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene

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Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.
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Related Experiment Video

Updated: Apr 30, 2026

Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework
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Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework

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Dithiolodithiole as a building block for conjugated materials.

Derek J Schipper1, Lionel C H Moh, Peter Müller

  • 1Department of Chemistry and Institute for Soldier Nanotechnologies, Massachusetts Institute of Technology, Cambridge, MA 02139 (USA).

Angewandte Chemie (International Ed. in English)
|April 30, 2014
PubMed
Summary

Researchers explored a new sulfur-based building block, dithiolodithiole (C4S4), for advanced organic materials. This offers stronger donor properties and tunable characteristics for applications in electronics and energy.

Keywords:
conjugated materialsheterocyclessulfursynthetic methodsthiophenes

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Scale-up Chemical Synthesis of Thermally-activated Delayed Fluorescence Emitters Based on the Dibenzothiophene-S,S-Dioxide Core

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Area of Science:

  • Materials Science
  • Organic Chemistry
  • Solid-State Physics

Background:

  • Conjugated organic materials are crucial for advanced electronics like OLEDs, sensors, and photovoltaics.
  • Current materials often rely on a limited set of building blocks, hindering property diversification.
  • There is a need for novel molecular architectures to enhance material performance.

Purpose of the Study:

  • To introduce and evaluate the dithiolodithiole (C4S4) heterocycle as a new conjugated building block.
  • To investigate the properties of organic materials derived from this novel building block.
  • To demonstrate the synthetic accessibility and tunability of C4S4-based materials.

Main Methods:

  • Synthesis of dithiolodithiole (C4S4) using catalytic processes.
  • Assembly of π-conjugated molecules and polymers incorporating the C4S4 motif.
  • Characterization of molecular and bulk properties, including electronic and structural features.

Main Results:

  • C4S4-based materials exhibit stronger donor characteristics compared to thiophene analogues.
  • High crystallinity was observed in the resulting organic materials.
  • A decreased Highest Occupied Molecular Orbital-Lowest Unoccupied Molecular Orbital (HOMO-LUMO) gap was achieved, beneficial for electronic applications.
  • Synthetic accessibility via catalytic routes was confirmed.

Conclusions:

  • The dithiolodithiole (C4S4) heterocycle is a promising building block for advanced conjugated organic materials.
  • C4S4-based materials offer unique and advantageous properties compared to existing systems.
  • The synthetic accessibility and tunability of C4S4 open new avenues for designing high-performance organic electronics.