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用于功能性卟啉阵列的钯催化交叉偶联策略

Pd-Catalyzed Cross Coupling Strategy for Functional Porphyrin Arrays.

作者信息

Wang Kaisheng, Osuka Atsuhiro, Song Jianxin

机构信息

College of Chemistry and Chemical Engineering, Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research (Ministry of Education of China), Key Laboratory of the Assembly and Application of Organic Functional Molecules of Hunan Province, Hunan Normal University, Changsha 410081, China.

出版信息

ACS Cent Sci. 2020 Dec 23;6(12):2159-2178. doi: 10.1021/acscentsci.0c01300. Epub 2020 Nov 16.

DOI:10.1021/acscentsci.0c01300
PMID:33376779
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7760067/
Abstract

Porphyrin arrays are an important class of compounds to study interporphyrin electronic interactions that are crucial in determining the rates of energy transfer and electron transfer reactions. When the electronic interactions become stronger, porphyrin arrays exhibit significantly altered optical and electronic properties owing to large oscillator strength and flexible electronic nature of porphyrins. In addition, porphyrins accept various metal cation in their cavities and the interporphyrin interactions depend upon the coordinated metal. With these in the background, porphyrin arrays have been extensively explored as sensors, multielectron catalysts, photodynamic therapy reagents, artificial photosynthetic antenna, nonlinear optical materials, and so on. Here, we review the synthesis of porphyrin arrays by palladium-catalyzed cross-coupling reactions, which are quite effective to construct carbon-carbon bonds and carbon-nitrogen bonds in porphyrin substrates. Palladium-catalyzed cross coupling reactions employed so far are Suzuki-Miyaura coupling reaction, Sonogashira coupling reaction, Buchwald-Hartwig amination, Mizoroki-Heck reaction, Migita-Kosugi-Stille coupling reaction, and so on. In each case, the representative examples and synthetic advantages are discussed.

摘要

卟啉阵列是一类重要的化合物，用于研究卟啉间的电子相互作用，这种相互作用对于确定能量转移和电子转移反应的速率至关重要。当电子相互作用增强时，由于卟啉具有较大的振子强度和灵活的电子性质，卟啉阵列会表现出显著改变的光学和电子性质。此外，卟啉在其空穴中能容纳各种金属阳离子，并且卟啉间的相互作用取决于配位金属。基于这些背景，卟啉阵列已被广泛探索用作传感器、多电子催化剂、光动力治疗试剂、人工光合天线、非线性光学材料等。在此，我们综述了通过钯催化的交叉偶联反应合成卟啉阵列的方法，这些反应在构建卟啉底物中的碳 - 碳键和碳 - 氮键方面非常有效。迄今为止所采用的钯催化交叉偶联反应有铃木 - 宫浦偶联反应、 Sonogashira 偶联反应、 Buchwald - Hartwig 胺化反应、 Mizoroki - Heck 反应、 Migita - Kosugi - Stille 偶联反应等。在每种情况下，都讨论了代表性实例和合成优势。

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Nat Commun. 2020 Oct 20;11(1):5289. doi: 10.1038/s41467-020-19118-9.
2
Regioselectively Halogenated Expanded Porphyrinoids as Building Blocks for Constructing Porphyrin-Porphyrinoid Heterodyads with Tunable Energy Transfer.区域选择性卤代扩展卟啉作为构建具有可调能量转移的卟啉-卟啉杂化物的结构单元。
J Am Chem Soc. 2019 Apr 3;141(13):5294-5302. doi: 10.1021/jacs.8b13148. Epub 2019 Mar 19.
3
Coordination-Induced Spin-State Switching of an Aminyl-Radical-Bridged Nickel(II) Porphyrin Dimer between Doublet and Sextet States.
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Chem Sci. 2022 Feb 28;13(12):3477-3488. doi: 10.1039/d2sc00174h. eCollection 2022 Mar 24.
4
Metal Complexes of Singly, Doubly and Triply Linked Porphyrins and Corroles: An Insight into the Physicochemical Properties.金属卟啉和Corrole 单核、双核和三核配合物：对物理化学性质的深入了解。
Chemistry. 2022 Apr 27;28(24):e202104550. doi: 10.1002/chem.202104550. Epub 2022 Mar 7.
5
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Chem Sci. 2021 Oct 29;12(44):14944-14951. doi: 10.1039/d1sc04893g. eCollection 2021 Nov 17.
6
Porphyrins as building blocks for single-molecule devices.卟啉作为单分子器件的构建模块。
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配位诱导氨基自由基桥联镍（II）卟啉二聚体在双重态和六重态之间的自旋态切换
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Angew Chem Int Ed Engl. 2018 Mar 26;57(14):3733-3736. doi: 10.1002/anie.201801080. Epub 2018 Mar 6.
5
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6
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7
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