5-Bromo-4-((2-ethylhexyl)oxy)-2-thiophenecarboxaldehyde (EHOThCHO-Br) is a thiophene derivative with multiple functional groups around the thiophene ring. Both bromo and aldehyde functional groups at 2,5-positions enable C-C formation to grow the chain length and extend its conjugation in the targeted semiconducting molecules. Ethylhexyloxyl group is there not only to enhance the solubility but also to lower the HOMO/LUMO energy levels of the targeted molecules. Comparing with the molecules bearing ethylhexyl group, molecules with ethylhexyloxyl side chains extend their absorption further to near infrared (NIR) region. 5-Bromo-4-((2-ethylhexyl)oxy)-2-thiophenecarboxaldehyde is a widely used building block that is used for the synthesis of ultra-narrow band-gap non-fullerene acceptors (NFAs) such as IEICO, IEICO-4F and IEICO-4Cl.
Absorption of IEICO-4F mainly locates in the deep-red and near infrared region, ranging from ~ 700 nm to ~ 1000 nm.
|Molecular weight||319.26 g/mol|
|Classification / Family||Thiophene derivatives, Organic semiconducting materials, Semiconductor Synthesis, Low band gap polymers, OFETs, OLED, Organic Photovoltaics, None-fullerene acceptors (NFAs), NFA-OSCs.|
Literature and Reviews
- Ultra-narrow bandgap non-fullerene organic solar cells with low voltage losses and a large photocurrent, J. Mater. Chem. A, 6, 19934-19940 (2018); DOI:10.1039/C8TA07954D.
- Improved charge transfer, mobility and morphology for high performance panchromatic organic photodetectors by adding PC71BM in P3HT:IEICO-4F, Y. Han et al., Org. Electron., 75, 105410 (2019); doi: 10.1016/j.orgel.2019.105410.
- 12.5% Flexible Nonfullerene Solar Cells by Passivating the Chemical Interaction Between the Active Layer and Polymer Interfacial Layer, S. Xiong et al., Adv Mater., 31(22):e1806616 (2019); doi: 10.1002/adma.201806616.
- Efficient Semitransparent Organic Solar Cells with Tunable Color enabled by an Ultralow Bandgap Nonfullerene Acceptor, Y Cui et al., Adv Mater. 29(43), 1703080 (2017); doi: 10.1002/adma.201703080.
- Controlling Blend Morphology for Ultrahigh Current Density in Nonfullerene Acceptor-Based Organic Solar Cells, X. Song et al., ACS Energy Lett., 3(3), 669-676 (2018); doi: 10.1021/acsenergylett.7b01266.
- Efficient Ternary Polymer Solar Cells with Two Well‐Compatible Donors and One Ultranarrow Bandgap Nonfullerene Acceptor, X. Ma et al., Adv. Energy Mater., 8 (11), 1702854 (2018); DOI: 10.1002/aenm.201702854.
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