University of PardubiceFaculty of Chemical Technology

University

Employees
|
Students
Česky

Publication detail

Chemodivergent photoreductions of nitroaromatics initiated by dithienoquinoxaline (DTQ)

Authors: Burešová Zuzana | Bureš Filip

Year: 2025

Type of publication: ostatní - přednáška nebo poster

Page from-to: nestránkováno

Titles:

Language	Name	Abstract	Keywords
eng	Chemodivergent photoreductions of nitroaromatics initiated by dithienoquinoxaline (DTQ)	The current photoredox catalysis allows to accomplish redox reactions under mild conditions via a photochemical activation of various substrates. Central to this methodology is a photocatalyst, which harness the light energy to drive the electron transfer processes. The common organic photoredox catalysts include dyes such as eosin Y and rhodamines, acridinium salts, flavins and dicyano(hetero)arenes. In 2014, we have developed X-shaped dicyanopyrazine (DPZ) photocatalyst and further addressed its synthesis and synthetic utility. The recent photophysical and theoretical study explained the DPZ’s mechanism of action and catalytic activity. Subsequently, we discovered that DPZ undergoes a Mallory-type cyclization under blue light irradiation affording dithienoquinoxaline (DTQ), which is the real catalytically active species. The double excited DTQ.– proved to be an very strong organic reductant with a reduction power of approx –3 V. Hence, DTQ may act as one-electron oxidant (3DTQ) as well as reductant (*DTQ.–) using a single light source. The latter reduction properties were utilized in a chemodivergent reduction of nitroaromatics towards nitroso, bis-(N,O-diacetyl)-N-arylhydroxylamine, azoxy, azo and amino derivatives, a fundamental task of both organic synthesis and chemical industry.	photoredox catalysis; dicyanopyrazine; nitroaromatics; reduction