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Electron Acceptors Based on Cyclopentannulated Anthanthrenes
The Journal of Organic Chemistry ( IF 3.6 ) Pub Date : 2021-01-04 , DOI: 10.1021/acs.joc.0c02197
Yachu Du 1 , Hope B. Lovell 1 , Frédéric Lirette 2 , Jean-François Morin 2 , Kyle N. Plunkett 1
Affiliation  

We demonstrate the preparation of anthanthrene derivatives with fused five-membered rings. These new derivatives are prepared by a palladium catalyzed cyclopentannulation reaction from precursors derived from the low-cost dye Vat Orange 3 (4,10-dibromoanthanthrone). The new cyclopentaanthanthrene compounds possess reduced optical and electrochemical gaps (∼0.9 eV) compared to anthanthrene derivatives and are electron acceptors with lowest unoccupied molecular orbital energies from ∼ −3.4 to −3.9 eV.

中文翻译:

基于环戊烷蒽的电子受体

我们展示了具有稠合五元环的蒽嵌蒽衍生物的制备。这些新的衍生物是通过钯催化的环戊烯醛化反应从廉价染料Vat Orange 3(4,10-dibromoanthanthrone)衍生的前体制备的。与蒽蒽衍生物相比,新的环戊蒽并蒽化合物具有减小的光学和电化学间隙(〜0.9 eV),并且是电子受体,其未占据的分子轨道能量最低,约为-3.4至-3.9 eV。
更新日期:2021-01-16
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