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Benzothienobenzothiophenes (BTBTs) are a class of heteroacenes for which two distinct isomers have been identified depending on the locations of the fused benzothiophene motifs. Benzothienobenzothiophenes represent a class of heteroacenes demonstrating remarkable electronic properties that make them prominent in the realm of organic semiconductors. The structure of BTBTs, incorporating two sulfur atoms, contributes to their unique electronic characteristics, including narrow bandgaps and effective charge transport pathways. These compounds have gained attention for their high charge carrier mobility, making them desirable candidates for application in organic field-effect transistors (OFETs) and other electronic devices. Researchers have explored various synthetic strategies to design and tailor the properties of BTBT derivatives, leading to advancements in the development of high-performance organic semiconductors. Various synthetic techniques for benzothienobenzothiophenes have been reported in the literature including multistep synthesis, tandem transformations, electrochemical synthesis, and annulations. This review investigates the generality of each synthetic methodology by highlighting its benefits and drawbacks, and it analyses all synthetic approaches described for the creation of the two isomers. For the advantage of the readers, we have delved upon every mechanism of the reactions that are known. Finally, we have also summarized the synthetic methodologies that are used for making benzothienobenzothiophene analogues for material applications.
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http://dx.doi.org/10.1002/tcr.202400019 | DOI Listing |
Chem Sci
March 2024
Department of Chemistry, Georgetown University USA
Pyrazinacenes are next generation N-heteroacenes and represent a novel class of stable n-type materials capable of accepting more than one electron and displaying intriguing features, including prototropism, halochromism, and redox chromism. Astonishingly, despite a century since their discovery, there have been no reports on the conjugated polymers of pyrazinacenes due to unknown substrate scope and lack of pyrazinacene monomers that are conducive to condensation polymerization. Breaking through these challenges, in this work, we report the synthesis of previously undiscovered and highly coveted conjugated polymers of pyrazinacenes.
View Article and Find Full Text PDFChem Rec
April 2024
Institut für Organische Chemie, Technische Universität Braunschweig, Hagenring 30, D-38106, Braunschweig, Germany.
Benzothienobenzothiophenes (BTBTs) are a class of heteroacenes for which two distinct isomers have been identified depending on the locations of the fused benzothiophene motifs. Benzothienobenzothiophenes represent a class of heteroacenes demonstrating remarkable electronic properties that make them prominent in the realm of organic semiconductors. The structure of BTBTs, incorporating two sulfur atoms, contributes to their unique electronic characteristics, including narrow bandgaps and effective charge transport pathways.
View Article and Find Full Text PDFSmall
April 2023
Beijing National Laboratory for Molecular Sciences, CAS Research/Education Center for Excellence in Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190, P. R. China.
Covalent organic frameworks (COFs) are a unique new class of porous materials that arrange building units into periodic ordered frameworks through strong covalent bonds. Accompanied with structural rigidity and well-defined geometry, heteroacene-based COFs have natural advantages in constructing COFs with high stability and crystallinity. Heteroacene-based COFs usually have high physical and chemical properties, and their extended π-conjugation also leads to relatively low energy gap, effectively promoting π-electron delocalization between network units.
View Article and Find Full Text PDFProc Natl Acad Sci U S A
July 2022
Chemistry and Nanosciences Center, National Renewable Energy Laboratory, Golden, CO 80401.
The photo-driven process of singlet fission generates coupled triplet pairs (TT) with fundamentally intriguing and potentially useful properties. The quintet TT sublevel is particularly interesting for quantum information because it is highly entangled, is addressable with microwave pulses, and could be detected using optical techniques. Previous theoretical work on a model Hamiltonian and nonadiabatic transition theory, called the model, has determined that this sublevel can be selectively populated if certain conditions are met.
View Article and Find Full Text PDFJ Org Chem
June 2022
Chemical Sciences and Technology Division, CSIR-National Institute for Interdisciplinary Science and Technology (CSIR-NIIST), Thiruvananthapuram 695019, India.