Related Experiment Video
Updated: May 7, 2026

Scale-up Chemical Synthesis of Thermally-activated Delayed Fluorescence Emitters Based on the Dibenzothiophene-S,S-Dioxide Core
Published on: October 24, 2017
Synthesis of thiophene 1,1-dioxides and tuning their optoelectronic properties
Chia-Hua Tsai1, Danielle N Chirdon, Andrew B Maurer
1Department of Chemistry, Carnegie Mellon University , 4400 Fifth Avenue, Pittsburgh , Pennsylvania, 15213, United States.
Abstract:
A 2,5-bis(tributylstannyl)thiophene 1,1-dioxide was prepared from 2,5-bis(trimethylsilyl)thiophene 1,1-dioxide, bis(tributyltin) oxide, and tetrabutylammonium fluoride (TBAF). The 2,5-bis(tributylstannyl)thiophene 1,1-dioxide and a 2,5-diiodothiophene 1,1-dioxide were utilized in a series of Stille cross-coupling reactions to afford thiophene 1,1-dioxides with either electron-donating or electron-withdrawing substituents. Electron-withdrawing groups greatly facilitate the reduction of these sulfone heterocycles, and -C6H4-p-NO2 substituents produce a 510 mV shift as compared to a thiophene 1,1-dioxide with two phenyl groups.
Related Concept Videos
Preparation and Reactions of Thiols
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
Thermal and Photochemical Electrocyclic Reactions: Overview
Photochemical Electrocyclic Reactions: Stereochemistry
Selection Rules: Photochemical Activation
Thermal Electrocyclic Reactions: Stereochemistry
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.
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

