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Thieno[3,4-b]thiophene-Based Novel Small-Molecule Optoelectronic Materials
Cheng Zhang1,2, Xiaozhang Zhu1,2
1Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Organic Solids, Institute of Chemistry, Chinese Academy of Sciences , Beijing 100190, P. R. China.
Accounts of Chemical Research
|April 5, 2017
Summary
Researchers developed novel thieno[3,4-b]thiophene (TbT)-based small molecules for organic optoelectronics. These materials exhibit tunable emissions and high performance in organic photovoltaics (OPVs) and organic field-effect transistors (OFETs).
Area of Science:
- Organic optoelectronics
- Materials science
- Supramolecular chemistry
Background:
- Organic π-functional materials are crucial for high-performance optoelectronic devices like OPVs, OFETs, and OLEDs.
- Small molecules offer advantages over polymers for establishing structure-property relationships in optoelectronic materials.
- Thiophene-based materials are vital, with thieno[3,4-b]thiophene (TbT) offering unique electronic modulation via its quinoid-resonance effect.
Purpose of the Study:
- To explore the largely untapped potential of TbT in small-molecule optoelectronic materials.
- To design and synthesize novel TbT-based small molecules utilizing quinoid-resonance effects, regiochemistry, and side-chain engineering.
- To investigate the impact of TbT building blocks on electronic structures, photophysical properties, charge transport, and photovoltaic performance.
Main Methods:
- Rational design and synthesis of TbT-based small-molecule optoelectronic materials.
- Investigation of quinoid-resonance effect and its geometric origins using regioregular oligothieno[3,4-b]thiophenes.
- Characterization of photophysical properties, including full-color tunable emissions and fluorescence quantum yields.
- Fabrication and testing of organic thin-film transistors (OTFTs) and organic photovoltaics (OPVs).
Main Results:
- TbT-based small molecules demonstrated full-color tunable emissions (visible to near-infrared) with high fluorescence quantum yields.
- Solution-processable, ambient-stable n-channel OTFTs based on 2D π-expanded quinoidal terthiophenes achieved electron mobility up to 5.2 cm²/Vs.
- TbT-based electron donor and acceptor materials for OPVs achieved high power conversion efficiencies of 9.26% and 10.07%, respectively.
Conclusions:
- The TbT building block significantly influences the electronic structure, photophysical, and charge transport properties of small-molecule optoelectronic materials.
- Synergistic molecular engineering strategies involving TbT can lead to enhanced performance in OFETs and OPVs.
- TbT-based small molecules hold promise for advancing organic optoelectronics and enabling novel device applications.