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Preparation and Reactions of Thiols02:33

Preparation and Reactions of Thiols

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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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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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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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[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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

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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.
13.8K
Preparation of Diols and Pinacol Rearrangement01:57

Preparation of Diols and Pinacol Rearrangement

4.4K
Compounds bearing two hydroxyl groups are known as diols. When the hydroxyl groups are located on adjacent carbon atoms, the diols are called vicinal diols or glycols. Under acidic conditions, vicinal diols undergo a specific reaction called pinacol rearrangement.
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
4.4K
Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)01:16

Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)

3.4K
Ring-opening metathesis polymerization or ROMP involves strained cycloalkenes as starting materials. The mechanism of ROMP proceeds by reacting cycloalkene with Grubbs catalyst to give metallacyclobutane intermediate which undergoes a ring-opening reaction to form new carbene. The new carbene reacts with another molecule of cycloalkene. Repetition of these steps leads to the formation of an unsaturated open-chain polymer product. All these steps are reversible, however, relieving the ring...
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Updated: Apr 6, 2026

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Multifaceted Regioregular Oligo(thieno[3,4-b]thiophene)s Enabled by Tunable Quinoidization and Reduced Energy Band

Feng Liu1, Guzmán L Espejo2, Shuhai Qiu1

  • 1†Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Organic Solids, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190, P. R. China.

Journal of the American Chemical Society
|July 18, 2015
PubMed
Summary

Researchers developed new oligo(thieno[3,4-b]thiophene)s for organic electronics. These materials offer tunable energy band gaps and unique colors, enabling advanced electrochromic devices.

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Area of Science:

  • Organic electronics
  • Materials science
  • Polymer chemistry

Background:

  • Thiophene-based materials are vital for organic electronics.
  • Modulating energy band gaps in oligothiophenes is challenging without push-pull systems.

Purpose of the Study:

  • To synthesize and characterize novel monodisperse oligo(thieno[3,4-b]thiophene) derivatives.
  • To explore their tunable energy band gaps, redox properties, and electrochromic behavior.

Main Methods:

  • Direct C-H arylation for efficient synthesis.
  • Characterization of regioregular structures.
  • Electrochemical and spectroscopic analysis.

Main Results:

  • Achieved synthesis of well-defined oligo(thieno[3,4-b]thiophene)s.
  • Demonstrated widely tunable energy band gaps and amphoteric redox properties.
  • Observed both anodic and cathodic electrochromism due to cation/anion stabilization.
  • Reported photoionized states and interconversion pathways (singlet exciton fission, intersystem crossing).

Conclusions:

  • Oligo(thieno[3,4-b]thiophene)s offer a unique platform for organic electronics.
  • Their planar structure and extended conjugation lead to distinctive electronic and optical properties.
  • These materials represent a significant advancement in oligothiophene chemistry for tunable optoelectronic applications.