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二苯并[]呋咱并[3,4 - ]喹喔啉类化合物:通过直接无过渡金属C-H官能团化的分子内环化反应合成及其电化学、光物理和电荷迁移率表征

Dibenzo[]furazano[3,4-]quinoxalines: Synthesis by Intramolecular Cyclization through Direct Transition Metal-Free C-H Functionalization and Electrochemical, Photophysical, and Charge Mobility Characterization.

作者信息

Kvashnin Yuriy A, Verbitskiy Egor V, Eltsov Oleg S, Slepukhin Pavel A, Tameev Alexey R, Nekrasova Natalia V, Rusinov Gennady L, Nunzi Jean-Michel, Chupakhin Oleg N, Charushin Valery N

机构信息

Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, S. Kovalevskoy Street 22, Ekaterinburg, 620108, Russia.

Ural Federal University, Mira Street 19, Ekaterinburg, 620002, Russia.

出版信息

ACS Omega. 2020 Mar 30;5(14):8200-8210. doi: 10.1021/acsomega.0c00479. eCollection 2020 Apr 14.

DOI:10.1021/acsomega.0c00479
PMID:32309730
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7161064/
Abstract

Herein, we describe the synthesis of unsymmetrically substituted dibenzo[]furazano[3,4-]quinoxalines by intramolecular cyclization through direct transition metal-free C-H functionalization. The electrochemical and photophysical properties for several polycycles have been measured. In thin films of the dibenzo[]furazano[3,4-]quinoxalines, hole mobility is in the order of 10 cm V s. The results show that the HOMO and LUMO energy levels are appropriate for using the compounds as hole-transport materials in thin-film devices, in particular, organic and perovskite solar cells.

摘要

在此,我们描述了通过直接无过渡金属的C-H官能化进行分子内环化来合成不对称取代的二苯并[]呋喃并[3,4-]喹喔啉。已测量了几种多环化合物的电化学和光物理性质。在二苯并[]呋喃并[3,4-]喹喔啉的薄膜中,空穴迁移率约为10 cm² V⁻¹ s⁻¹。结果表明,最高占据分子轨道(HOMO)和最低未占据分子轨道(LUMO)能级适合将这些化合物用作薄膜器件,特别是有机和钙钛矿太阳能电池中的空穴传输材料。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b346/7161064/cc9b27e3f0e2/ao0c00479_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b346/7161064/036e88918793/ao0c00479_0011.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b346/7161064/cea11c0d049b/ao0c00479_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b346/7161064/581a7a5c3c85/ao0c00479_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b346/7161064/f37e6aaea2cc/ao0c00479_0010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b346/7161064/2eac2a09beb9/ao0c00479_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b346/7161064/0fc075d956ab/ao0c00479_0009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b346/7161064/cc9b27e3f0e2/ao0c00479_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b346/7161064/036e88918793/ao0c00479_0011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b346/7161064/db61b7c65d8a/ao0c00479_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b346/7161064/99a55056e199/ao0c00479_0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b346/7161064/cea11c0d049b/ao0c00479_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b346/7161064/581a7a5c3c85/ao0c00479_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b346/7161064/f37e6aaea2cc/ao0c00479_0010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b346/7161064/2eac2a09beb9/ao0c00479_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b346/7161064/0fc075d956ab/ao0c00479_0009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b346/7161064/cc9b27e3f0e2/ao0c00479_0002.jpg

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