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锯齿形纳米石墨烯二酮的亲核加成规则*

Rules of Nucleophilic Additions to Zigzag Nanographene Diones*.

作者信息

Ribar Peter, Valenta Leoš, Šolomek Tomáš, Juríček Michal

机构信息

Department of Chemistry, University of Basel, St. Johanns-Ring 19, 4056, Basel, Switzerland.

Department of Chemistry, University of Zurich, Winterthurerstrasse 190, 8057, Zurich, Switzerland.

出版信息

Angew Chem Int Ed Engl. 2021 Jun 7;60(24):13521-13528. doi: 10.1002/anie.202016437. Epub 2021 May 4.

DOI:10.1002/anie.202016437
PMID:33645878
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8251702/
Abstract

Nucleophilic addition of carbon-centered nucleophiles to nanographene ketones represents a valuable late-stage method for the functionalization of zigzag nanographenes, but its use is rare in the chemical literature. Using two model systems, non-Kekulé triangulene-4,8-dione and Kekulé anthanthrone, we identify unexpected regioselectivities and uncover the rules that govern these reactions. Considering the large number of nanographene ketones that have been reported since the pioneering work of Eric Clar, this method enables synthesis and exploration of hitherto unknown functionalized nanographenes.

摘要

以碳为中心的亲核试剂对纳米石墨烯酮的亲核加成反应，是一种用于锯齿形纳米石墨烯功能化的重要后期方法，但在化学文献中其应用较少。我们使用两个模型体系，即非凯库勒三角烯-4,8-二酮和凯库勒蒽酮，确定了意外的区域选择性，并揭示了控制这些反应的规则。鉴于自埃里克·克拉尔开创性工作以来已报道了大量的纳米石墨烯酮，该方法能够合成和探索迄今未知的功能化纳米石墨烯。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/927e/8251702/4cc1cd9c5ee0/ANIE-60-13521-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/927e/8251702/d07a307a6531/ANIE-60-13521-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/927e/8251702/2fbb973f0517/ANIE-60-13521-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/927e/8251702/bc65f962de1f/ANIE-60-13521-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/927e/8251702/00d4c67b6098/ANIE-60-13521-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/927e/8251702/9df17e1f79f2/ANIE-60-13521-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/927e/8251702/3bda5923ec70/ANIE-60-13521-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/927e/8251702/1bdaa11d4899/ANIE-60-13521-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/927e/8251702/9ab16548c1c3/ANIE-60-13521-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/927e/8251702/4cc1cd9c5ee0/ANIE-60-13521-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/927e/8251702/d07a307a6531/ANIE-60-13521-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/927e/8251702/2fbb973f0517/ANIE-60-13521-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/927e/8251702/bc65f962de1f/ANIE-60-13521-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/927e/8251702/00d4c67b6098/ANIE-60-13521-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/927e/8251702/9df17e1f79f2/ANIE-60-13521-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/927e/8251702/3bda5923ec70/ANIE-60-13521-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/927e/8251702/1bdaa11d4899/ANIE-60-13521-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/927e/8251702/9ab16548c1c3/ANIE-60-13521-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/927e/8251702/4cc1cd9c5ee0/ANIE-60-13521-g003.jpg

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4
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Energy Sci Eng. 2022 May;10(5):1752-1762. doi: 10.1002/ese3.1071. Epub 2022 Jan 17.
5
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Chem Commun (Camb). 2022 Mar 1;58(18):3019-3022. doi: 10.1039/d2cc00352j.
J Am Chem Soc. 2019 Feb 20;141(7):3240-3248. doi: 10.1021/jacs.8b13300. Epub 2019 Feb 8.
4
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Molecules. 2018 Dec 30;24(1):118. doi: 10.3390/molecules24010118.
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