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A Promising Nonfullerene Acceptor Containing Boron-Oxygen Heterocycle
Yuhong Long1, Qiaorong Liu1, Shuhui Ding1
1State Key Laboratory of Elemento-Organic Chemistry, Frontiers Science Center for New Organic Matter, The Centre of Nanoscale Science and Technology and Key Laboratory of Functional Polymer Materials, Institute of Polymer Chemistry, College of Chemistry, Renewable Energy Conversion and Storage Center (RECAST), Frontiers Science Center for New Organic Matter, Nankai University, Tianjin 300071, China.
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Exploring nonfullerene acceptors (NFAs) with high luminescent structural "genes" is crucial for suppressing the nonradiative recombination in organic solar cells (OSCs). Herein, a boron-oxygen six-membered heterocycle is first employed to afford two conformationally distinct NFA isomers of CH-S and CH-C. Owing to the electron-lacking nature of boron atoms, both CH-S and CH-C demonstrate a relatively wide bandgap. Interestingly, different ring-fused pathways yield the typical S- and C-shaped molecular conformations, which not only dominate their distinctive intermolecular packing modes but also greatly exert on the fundamental luminescent and optoelectronic properties. Consequently, CH-C-based binary OSCs achieve an excellent efficiency of 11.03%, ranking among the highest values reported for wide-bandgap acceptors with absorption cutoffs below 750 nm. This work first highlights the significant potential of boron-oxygen heterocycles for constructing high-performance wide-bandgap NFAs.
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One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
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Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.