Replication Data for: "A flavin-inspired covalent organic framework for photocatalytic alcohol oxidation"

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Trenker, Stefan; Grunenberg, Lars; Banerjee, Tanmay; Savasci, Gökcen; Poller, Laura M.; Muggli, Katharina I. M.; Haase, Frederik; Ochsenfeld, Christian; Lotsch, Bettina, 2023, "Replication Data for: "A flavin-inspired covalent organic framework for photocatalytic alcohol oxidation"", https://doi.org/10.18419/darus-2244, DaRUS, V1

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Description	Covalent organic frameworks (COFs) offer a number of key properties that predestine them to be used as heterogeneous photocatalysts, including intrinsic porosity, long-range order, and light absorption. Since COFs can be constructed from a practically unlimited library of organic building blocks, these properties can be precisely tuned by choosing suitable linkers. Herein, we report the construction and use of a novel COF (FEAx-COF) photocatalyst, inspired by natural flavin cofactors. We show that the functionality of the alloxazine chromophore incorporated into the COF backbone is retained and study the effects of this heterogenization approach by comparison with similar molecular photocatalysts. We find that the integration of alloxazine chromophores into the framework significantly extends the absorption spectrum into the visible range, allowing for photocatalytic oxidation of benzylic alcohols to aldehydes even with low-energy visible light. In addition, the activity of the heterogeneous COF photocatalyst is less dependent on the chosen solvent, making it more versatile compared to molecular alloxazines. Finally, the use of oxygen as the terminal oxidant renders FEAx-COF a promising and “green” heterogeneous photocatalyst. All primary data files of measurements and processed data of the journal article mentioned under related publications from Lotsch group can be found here. The dataset contains data for the following analytical techniques: SEM, TEM, XPRD, scXRD, NMR, IR, UV-Vis, Sorption. (2021-11-24)
Subject	Chemistry
Keyword	Covalent Organic Framework, Photocatalysis
Related Publication	Stefan Trenker, Lars Grunenberg, Tanmay Banerjee, Gökcen Savasci, Laura M. Poller, Katharina I. M. Muggli, Frederik Haase, Christian Ochsenfeld and Bettina V. Lotsch. A flavin-inspired covalent organic framework for photocatalytic alcohol oxidation. Chem. Sci., 2021,12, 15143-15150.doi: 10.1039/D1SC04143F
Data Generation	Simulation; Analysis; Experiment
License/Data Use Agreement	CC BY 4.0

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	IR FEAx COF.asc IR/Fixed Field Text Data - 44.4 KB Published Jul 18, 2023 0 Downloads MD5: 7acdbe9d29013720617732c18da0b7ff	Access File File Access Restricted Request Access Download Metadata Data File Citation EndNote XML RIS BibTeX
	IR FEAx Linker.asc IR/Fixed Field Text Data - 87.2 KB Published Jul 18, 2023 0 Downloads MD5: a49de7a791ed4986db38c4434b621a19	Access File File Access Restricted Request Access Download Metadata Data File Citation EndNote XML RIS BibTeX
	IR FEAx-COF stability 2xcat.asc IR/Fixed Field Text Data - 88.3 KB Published Jul 18, 2023 0 Downloads MD5: b5fac875e05688140eb70aafe5d5b4cb	Access File File Access Restricted Request Access Download Metadata Data File Citation EndNote XML RIS BibTeX
	IR FEAx-COF stability benzene.asc IR/Fixed Field Text Data - 88.3 KB Published Jul 18, 2023 0 Downloads MD5: b2428047c915f5c3be57053f3700782e	Access File File Access Restricted Request Access Download Metadata Data File Citation EndNote XML RIS BibTeX
	IR FEAx-COF stability DMF.asc IR/Fixed Field Text Data - 88.3 KB Published Jul 18, 2023 0 Downloads MD5: d2dbfcbbf11ab945512da9719f170369	Access File File Access Restricted Request Access Download Metadata Data File Citation EndNote XML RIS BibTeX
	IR FEAx-COF stability DMF2.asc IR/Fixed Field Text Data - 88.3 KB Published Jul 18, 2023 0 Downloads MD5: 64a4cfa9143daf67f45566377ecba6fe	Access File File Access Restricted Request Access Download Metadata Data File Citation EndNote XML RIS BibTeX
	IR FEAx-COF stability HCl.asc IR/Fixed Field Text Data - 88.3 KB Published Jul 18, 2023 0 Downloads MD5: 1e54d5cf4431a1e86a2c832972f3c4a4	Access File File Access Restricted Request Access Download Metadata Data File Citation EndNote XML RIS BibTeX
	IR FEAx-COF stability NaOH.asc IR/Fixed Field Text Data - 88.3 KB Published Jul 18, 2023 0 Downloads MD5: d01be45b3c1a91707caf4c30161984b0	Access File File Access Restricted Request Access Download Metadata Data File Citation EndNote XML RIS BibTeX
	IR FEAx-COF stability photocat.asc IR/Fixed Field Text Data - 180.9 KB Published Jul 18, 2023 0 Downloads MD5: 04b6e9a8d4ba98968d523fcafe0e5902	Access File File Access Restricted Request Access Download Metadata Data File Citation EndNote XML RIS BibTeX
	IR FEAx-COF stability photocat2.asc IR/Fixed Field Text Data - 176.2 KB Published Jul 18, 2023 0 Downloads MD5: 8fddc811aee7d79d71fabde156618d80	Access File File Access Restricted Request Access Download Metadata Data File Citation EndNote XML RIS BibTeX

Citation Metadata

Persistent Identifier	doi:10.18419/darus-2244
Publication Date	2023-07-18
Title	Replication Data for: "A flavin-inspired covalent organic framework for photocatalytic alcohol oxidation"
Author	Trenker, Stefan (Max Planck Institute for Solid State Research) - ORCID: 0000-0002-6527-4489 Grunenberg, Lars (Max Planck Institute for Solid State Research) - ORCID: 0000-0002-6831-4626 Banerjee, Tanmay (Birla Institute of Technology and Science Pilani) - ORCID: 0000-0002-4548-2117 Savasci, Gökcen (University of Munich (LMU)) - ORCID: 0000-0002-6183-7715 Poller, Laura M. (University of Munich (LMU)) Muggli, Katharina I. M. (University of Munich (LMU)) Haase, Frederik (Karlsruhe Institute of Technology (KIT)) - ORCID: 0000-0003-1156-033X Ochsenfeld, Christian (University of Munich (LMU)) - ORCID: 0000-0002-4189-6558 Lotsch, Bettina (Max Planck Institute for Solid State Research) - ORCID: 0000-0002-3094-303X
Point of Contact	Use email button above to contact. Lotsch, Bettina (Max Planck Institute for Solid State Research)
Description	Covalent organic frameworks (COFs) offer a number of key properties that predestine them to be used as heterogeneous photocatalysts, including intrinsic porosity, long-range order, and light absorption. Since COFs can be constructed from a practically unlimited library of organic building blocks, these properties can be precisely tuned by choosing suitable linkers. Herein, we report the construction and use of a novel COF (FEAx-COF) photocatalyst, inspired by natural flavin cofactors. We show that the functionality of the alloxazine chromophore incorporated into the COF backbone is retained and study the effects of this heterogenization approach by comparison with similar molecular photocatalysts. We find that the integration of alloxazine chromophores into the framework significantly extends the absorption spectrum into the visible range, allowing for photocatalytic oxidation of benzylic alcohols to aldehydes even with low-energy visible light. In addition, the activity of the heterogeneous COF photocatalyst is less dependent on the chosen solvent, making it more versatile compared to molecular alloxazines. Finally, the use of oxygen as the terminal oxidant renders FEAx-COF a promising and “green” heterogeneous photocatalyst. All primary data files of measurements and processed data of the journal article mentioned under related publications from Lotsch group can be found here. The dataset contains data for the following analytical techniques: SEM, TEM, XPRD, scXRD, NMR, IR, UV-Vis, Sorption. (2021-11-24)
Subject	Chemistry
Keyword	Covalent Organic Framework https://www.wikidata.org/wiki/Q5178887 (Wikidata) Photocatalysis https://www.wikidata.org/wiki/Q218831 (Wikidata)
Related Publication	Stefan Trenker, Lars Grunenberg, Tanmay Banerjee, Gökcen Savasci, Laura M. Poller, Katharina I. M. Muggli, Frederik Haase, Christian Ochsenfeld and Bettina V. Lotsch. A flavin-inspired covalent organic framework for photocatalytic alcohol oxidation. Chem. Sci., 2021,12, 15143-15150. doi 10.1039/D1SC04143F https://doi.org/10.1039/D1SC04143F
Language	English
Funding Information	DFG: 358283783 - SFB 1333 DFG: EXC2089 European Commission: info:eu-repo/grantAgreement/EC/H2020/639233
Project	Project A3 (Level 1)
Depositor	Trenker, Stefan
Deposit Date	2021-11-25
Data Type	experimental data
Related Dataset	Related data has been deposited in the Cambridge Crystallographic Data Centre (CCDC) PEAx: Stefan Trenker, Lars Grunenberg, Tanmay Banerjee, Gökcen Savasci, Laura M. Poller, Katharina I. M. Muggli, Frederik Haase, Christian Ochsenfeld, Bettina V. Lotsch CCDC 2097444: Experimental Crystal Structure Determination, 2021, DOI: 10.5517/ccdc.csd.cc28dkhr; HEAx: Stefan Trenker, Lars Grunenberg, Tanmay Banerjee, Gökcen Savasci, Laura M. Poller, Katharina I. M. Muggli, Frederik Haase, Christian Ochsenfeld, Bettina V. Lotsch CCDC 2097424: Experimental Crystal Structure Determination, 2021, DOI: 10.5517/ccdc.csd.cc28djv2

Process Metadata

Processing Methods	HPLC (high performance liquid chromatography) NMR (nuclear magnetic resonance spectrometry) scXRD (single-crystal X-ray diffraction) XRPD (X-ray powder diffraction) Physisorption UV-Vis spectroscopy FTIR (infrared spectroscopy) Elemental analysis TGA (thermogravimetric analysis) SEM (scanning electron microscopy) TEM (transmission electron microscopy) EPR (electron paramagnetic resonance) MS (mass spectrometry)
Software	Agilent ChemStation ASiQwin Version: 3.01 Materials Studio Version: 6.0.0 PERKIN ELMER ChemDraw Version: 16.0.0.82
Instruments	Agilent 1290 Infinity II LC (HPLC-MS) , Software: ChemStation BRUKER AV400TR (NMR Spectrometer (solution)) JEOL Eclipse 400+ (NMR Spectrometer (solution)) BRUKER Neo 600 MHz (NMR Spectrometer (solid-state)) BRUKER D8 Venture (X-ray diffractometer (single-crystal)) BRUKER D8 Discovery (X-ray diffractometer (powder)) QUANTACHROME INSTRUMENTS Autosorb iQ MP (Physisorption instrument) , Software: ASiQwin Agilent Cary 60 (UV-Vis spectrometer) PERKIN ELMER Spektrum BX II FT-IR (IR spectrometer) ELEMENTAR vario EL (Elemental analyzer) Netzsch STA 449 F5 Jupiter (Thermal analyzer) ZEISS Merlin (Scanning electron microsope) PHILIPS CM 30 ST (Transmission electron microscope) BRUKER EMXnano (EMX spectrometer) THERMO FINNIGAN MAT 90 (Mass spectrometer)

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Data Generation	Simulation; Analysis; Experiment

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