Related Experiment Video
Updated: May 2, 2026

Scale-up Chemical Synthesis of Thermally-activated Delayed Fluorescence Emitters Based on the Dibenzothiophene-S,S-Dioxide Core
Published on: October 24, 2017
Thieno[3,4-b]pyrazine-based oligothiophenes: simple models of donor-acceptor polymeric materials
Li Wen1, Christopher L Heth, Seth C Rasmussen
1Department of Chemistry and Biochemistry, North Dakota State University, NDSU Dept. 2735, P.O. Box 6050, Fargo, ND 58108, USA. seth.rasmussen@ndsu.edu.
Abstract:
A series of thieno[3,4-b]pyrazine-based oligomers were synthesized via Stille cross-coupling as models of electronic structure-function relationships in thieno[3,4-b]pyrazine-based conjugated materials. The prepared oligomers include two oligothieno[3,4-b]pyrazine series from monomer to trimer, as well as a series of mixed terthienyls in which the ratio of thieno[3,4-b]pyrazine to either thiophene or 3,4-ethylene-dioxythiophene has been varied. The full oligomeric series was then thoroughly investigated via photo-physical and electrochemical studies, along with theoretical calculations, in order to correlate the effect of conjugation length and oligomer composition with the resulting electronic and optical properties. The corresponding relationships revealed should then provide more advanced models for the elucidation of donor-acceptor interactions in both homopolymeric and copolymeric materials of thieno[3,4-b]pyrazines.
Related Concept Videos
Thermal and Photochemical Electrocyclic Reactions: Overview
Aromatic Hydrocarbon Cations: Structural Overview
Removing one hydrogen from the intervening CH2 group...
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Ziegler–Natta Chain-Growth Polymerization: Overview
Cationic Chain-Growth Polymerization: Mechanism
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.

