An electron-deficient MOF as an efficient electron-transfer catalyst for selective oxidative carbon-carbon coupling of 2,6-di-tert-butylphenol.

Naphthalene diimides (NDIs), a type of electron-deficient dye molecule with high quadrupole moment and excellent redox activity, have been utilized in various fields, such as energy transfer, chemical sensing, anion transport, and photo-/electrochromic materials. In this study, an electron-deficient metal-organic framework with one-dimensional channels, Eu2(BBNDI)3(DMF)2 (MOF 1) (H2BBNDI = N,N'-bis(3-benzoic acid)naphthalene diimide), was successfully constructed based on the naphthalene diimide derivative. Because of the generation of NDI radicals by electron transfer between components, this material exhibits fast-responsive reversible photochromic properties. Moreover, it shows high efficiency and selective oxidation of 2,6-di-tert-butylphenol to its quinone derivative, aldehyde, and dimeric or trimeric phenol derivative by controlling the reaction conditions.

[1]  S. Minteer,et al.  Advances on the Merger of Electrochemistry and Transition Metal Catalysis for Organic Synthesis. , 2021, Chemical reviews.

[2]  B. Liu,et al.  Transition-Metal-Catalyzed, Coordination-Assisted Functionalization of Nonactivated C(sp3)-H Bonds. , 2021, Chemical reviews.

[3]  Xin Zhao,et al.  Dual-Metal Hetero-Single-Atoms with Different Coordination for Efficient Synergistic Catalysis. , 2021, Journal of the American Chemical Society.

[4]  Yanan Li,et al.  A host–guest semibiological photosynthesis system coupling artificial and natural enzymes for solar alcohol splitting , 2021, Nature Communications.

[5]  Hui Xu,et al.  Mizoroki-Heck Reaction of Unstrained Aryl Ketones via Ligand-Promoted C-C Bond Olefination. , 2021, Organic letters.

[6]  Wenbin Lin,et al.  Integration of Earth-Abundant Photosensitizers and Catalysts in Metal–Organic Frameworks Enhances Photocatalytic Aerobic Oxidation , 2021 .

[7]  Allison M. Rice,et al.  Photophysics Modulation in Photoswitchable Metal-Organic Frameworks. , 2020, Chemical reviews.

[8]  B. Herrera,et al.  Mechanistic Insight Towards Understanding the Role of Charge in Thiourea Organocatalysis. , 2019, The Journal of organic chemistry.

[9]  Dongyang Chen,et al.  The impact of vertical π-extension on redox mechanisms of aromatic diimide dyes , 2019 .

[10]  Y. Zhao,et al.  Engineering Donor-acceptor Heterostructure Crystals for Photonic Logic Computation. , 2019, Angewandte Chemie.

[11]  X. Bu,et al.  Synergistically Directed Assembly of Aromatic Stacks Based Metal‐Organic Frameworks by Donor‐Acceptor and Coordination Interactions , 2019, Chinese Journal of Chemistry.

[12]  J. Niu,et al.  Ternary supramolecular system for photocatalytic oxidation with air by consecutive photo-induced electron transfer processes , 2019, Journal of Catalysis.

[13]  T. Bell,et al.  Harnessing Brightness in Naphthalene Diimides. , 2019, Chemistry.

[14]  M. Yamashita,et al.  Porous Molecular Conductor: Electrochemical Fabrication of Through-Space Conduction Pathways among Linear Coordination Polymers. , 2019, Journal of the American Chemical Society.

[15]  T. Campo,et al.  Chemoselectivity Switching in the Rhodium-Catalyzed Reactions of 4-Substituted-1-sulfonyl-1,2,3-triazoles with Allenols: Noticeable Differences between 4-Acyl- and 4-Aryl-Triazoles , 2019, Advanced Synthesis & Catalysis.

[16]  H. Yorimitsu,et al.  Iridium-Catalyzed Direct Hydroarylation of Glycals via C–H Activation: Ligand-Controlled Stereoselective Synthesis of α- and β-C-Glycosyl Arenes , 2019, ACS Catalysis.

[17]  Jian Zhu,et al.  Structure and Emission Modulation of a Series of Cd(II) Luminescent Coordination Polymers through Guest Dependent Donor–Acceptor Interaction , 2019, Crystal Growth & Design.

[18]  Jian Zhu,et al.  Rational Construction of Highly Tunable Donor–Acceptor Materials Based on a Crystalline Host–Guest Platform , 2018, Advanced materials.

[19]  K. Nozaki,et al.  Branched-Selective Hydroformylation of Nonactivated Olefins Using an N-Triphos/Rh Catalyst , 2018 .

[20]  B. Tan,et al.  Construction of Axially Chiral Compounds via Asymmetric Organocatalysis. , 2018, Accounts of chemical research.

[21]  F. Tao,et al.  C-C Coupling on Single-Atom-Based Heterogeneous Catalyst. , 2018, Journal of the American Chemical Society.

[22]  S. Matile,et al.  Electric-Field-Assisted Anion-π Catalysis. , 2017, Journal of the American Chemical Society.

[23]  Guangbin Dong,et al.  Transition-Metal-Catalyzed C − H Alkylation Using Alkenes , 2017 .

[24]  Na Li,et al.  Host-Guest Engineering of Coordination Polymers for Highly Tunable Luminophores Based on Charge Transfer Emissions. , 2017, ACS applied materials & interfaces.

[25]  S. Bhosale,et al.  Functional Naphthalene Diimides: Synthesis, Properties, and Applications. , 2016, Chemical reviews.

[26]  Mircea Dincă,et al.  Transparent-to-Dark Electrochromic Behavior in Naphthalene-Diimide-Based Mesoporous MOF-74 Analogs , 2016 .

[27]  D. Dhavale,et al.  Synthesis of 2,4,6-Trisubstituted Pyridines by Oxidative Eosin Y Photoredox Catalysis. , 2016, The Journal of organic chemistry.

[28]  David A. Nicewicz,et al.  Organic Photoredox Catalysis. , 2016, Chemical reviews.

[29]  W. Eisenreich,et al.  Photoreforming of ethylene glycol over Rh/TiO2 and Rh/GaN:ZnO , 2016 .

[30]  Magnus Rueping,et al.  Catalytic C-C bond-forming multi-component cascade or domino reactions: pushing the boundaries of complexity in asymmetric organocatalysis. , 2014, Chemical reviews.

[31]  S. Matile,et al.  Catalysis with anion-π interactions. , 2013, Angewandte Chemie.

[32]  Lei Yu,et al.  Syntheses, Crystal Structures, and Physical Properties of Two Noninterpenetrated Pillar-Layered Metal–Organic Frameworks Based on N,N′-Di(4-pyridyl)-1,4,5,8-naphthalenetetracarboxydiimide Pillar , 2013 .

[33]  J. Bode,et al.  Catalytic selective synthesis. , 2012, Angewandte Chemie.

[34]  C. Parmeggiani,et al.  Transition metal based catalysts in the aerobic oxidation of alcohols , 2012 .

[35]  C. Yeung,et al.  Catalytic dehydrogenative cross-coupling: forming carbon-carbon bonds by oxidizing two carbon-hydrogen bonds. , 2011, Chemical reviews.

[36]  S. Saha,et al.  Fluoride ion sensing by an anion-π interaction. , 2010, Journal of the American Chemical Society.

[37]  Alexander M. Spokoyny,et al.  Chemical reduction of a diimide based porous polymer for selective uptake of carbon dioxide versus methane. , 2010, Chemical communications.

[38]  Lunxiang Yin,et al.  Carbon-carbon coupling reactions catalyzed by heterogeneous palladium catalysts. , 2007, Chemical reviews.

[39]  G. Rothenberg,et al.  Palladium Nanoclusters in Sonogashira Cross-Coupling: A True Catalytic Species? , 2005 .

[40]  T. Hyeon,et al.  Designed synthesis of atom-economical pd/ni bimetallic nanoparticle-based catalysts for sonogashira coupling reactions. , 2004, Journal of the American Chemical Society.

[41]  M. Ochiai,et al.  Substrate-Specific Rearrangement and Acetonidation of Epoxy-Ethers Catalyzed by Tetracyanoethylene , 1993 .

[42]  K. Tanemura,et al.  2,3-Dichloro-5,6-dicyano-p-benzoquinone as a mild and efficient catalyst for the deprotection of acetals , 1992 .