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Updated: Jun 5, 2025

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

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Published on: October 24, 2017

Exploring Benzothieno[3,2-b]benzothiophene S-Oxides for Organic Electronics, Fluorescence-Based Applications, and

Aneta Rzewnicka¹, Maciej Mikina¹, Jerzy Krysiak¹

¹Division of Organic Chemistry, Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza 112, 90-363, Lodz, Poland.

Chemistry (Weinheim an Der Bergstrasse, Germany)

|December 13, 2024

Abstract:

A series of benzothieno[3,2-b]benzothiophene S-oxides has been efficiently synthesized via one- or two-step selective oxidation of benzothieno[3,2-b]benzothiophene (BTBT). These BTBT S-oxides form highly ordered structures that display optical anisotropy, are thermally stable up to temperatures above 210 °C, and do not show phase transitions. They exhibit long excited state lifetimes (0.181-0.869 ms) and are more resistant to oxidative degradation than their parent unoxidized BTBT. Some of these compounds demonstrate high quantum yields, exceeding 98 % in solution and 71 % in the solid state. As evidenced by quantum-chemical calculations, BTBT-based sulfoxides have sufficiently high pyramidal inversion energy barriers that prevent their stereomutation at room temperature. Additionally, fully S-oxidized BTBT meets the energy-splitting criterion required for the singlet fission process, with the T₁ energy level that makes it suitable for device application.

Keywords:

Benzothienobenzothiophene S-oxides Fluorescence Quantum-chemical calculations Semiconductors Singlet fission

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