Pore Environment Effects on Catalytic Cyclohexane Oxidation in Expanded Fe2 (dobdc) Analogues

Xiao, Dianne J.; Oktawiec, Julia; Milner, Phillip J.; Long, Jeffrey R.

doi:10.1021/jacs.6b08417

Title: Pore Environment Effects on Catalytic Cyclohexane Oxidation in Expanded Fe₂ (dobdc) Analogues

Journal Article · Wed Oct 05 00:00:00 EDT 2016 · Journal of the American Chemical Society

DOI:https://doi.org/10.1021/jacs.6b08417· OSTI ID:1458984

Xiao, Dianne J. ^[1]; Oktawiec, Julia ^[1]; Milner, Phillip J. ^[1]; Long, Jeffrey R. ^[2]

Univ. of California, Berkeley, CA (United States)
Univ. of California, Berkeley, CA (United States); Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)

Here, metal–organic frameworks are a new class of heterogeneous catalysts in which molecular-level control over both the immediate and long-range chemical environment surrounding a catalytic center can be readily achieved. Here, the oxidation of cyclohexane to cyclohexanol and cyclohexanone is used as a model reaction to investigate the effect of a hydrophobic pore environment on product selectivity and catalyst stability in a series of iron-based frameworks. Specifically, expanded analogues of Fe₂(dobdc) (dobdc^4– = 2,5-dioxido-1,4-benzenedicarboxylate) were synthesized and evaluated, including the biphenyl derivative Fe₂(dobpdc) (H₄dobpdc = 4,4¢-dihydroxy-[1,1¢-biphenyl]-3,3¢-dicarboxylic acid), the terphenyl derivative Fe₂(dotpdc) (H₄dotpdc = 4,4¢¢-dihydroxy-[1,1¢:4¢,1¢¢-terphenyl]-3,3¢¢-dicarboxylic acid), and three modified terphenyl derivatives in which the central ring is replaced with tetrafluoro-, tetramethyl-, or di-tert-butylaryl groups. Within these five materials, a remarkable three-fold enhancement of the alcohol:ketone (A:K) ratio and an order of magnitude increase in turnover number is achieved by simply altering the framework pore diameter and installing nonpolar functional groups near the iron site. Mössbauer spectroscopy, kinetic isotope effect, and gas adsorption measurements reveal that variations in the A:K selectivities arise from differences in the cyclohexane adsorption enthalpies of these frameworks, which become more favorable as the number of hydrophobic residues and thus van der Waals interactions increases.

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Research Organization:: Univ. of Minnesota, Minneapolis, MN (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: FG02-12ER16362; SC0008688

OSTI ID:: 1458984

Journal Information:: Journal of the American Chemical Society, Vol. 138, Issue 43; ISSN 0002-7863

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 120 works

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Effective and Selective Catalysts for Cinnamaldehyde Hydrogenation: Hydrophobic Hybrids of Metal-Organic Frameworks, Metal Nanoparticles, and Micro- and Mesoporous Polymers Yuan, Kuo; Song, Tianqun; Wang, Dawei Angewandte Chemie International Edition, Vol. 57, Issue 20 https://doi.org/10.1002/anie.201801289	journal	March 2018
Encapsulation of Crabtree's Catalyst in Sulfonated MIL-101(Cr): Enhancement of Stability and Selectivity between Competing Reaction Pathways by the MOF Chemical Microenvironment Grigoropoulos, Alexios; McKay, Alasdair I.; Katsoulidis, Alexandros P. Angewandte Chemie International Edition, Vol. 57, Issue 17 https://doi.org/10.1002/anie.201710091	journal	March 2018
A series of new mixed-ligand complexes based on 3,6-bis(imidazol-1-yl)pyridazine: syntheses, structures, and catalytic activities Zhou, Sheng-Bin; Wang, Xin-Fang; Du, Ceng-Ceng CrystEngComm, Vol. 19, Issue 23 https://doi.org/10.1039/c7ce00394c	journal	January 2017
Fine tuning of catalytic and sorption properties of metal–organic frameworks via in situ ligand exchange Wang, Peng; Chen, Kai; Liu, Qing Dalton Transactions, Vol. 46, Issue 34 https://doi.org/10.1039/c7dt02231j	journal	January 2017
A complex metal-organic framework catalyst for microwave-assisted radical polymerization Nguyen, Ha L.; Vu, Thanh T.; Nguyen, Dinh-Khoi Communications Chemistry, Vol. 1, Issue 1 https://doi.org/10.1038/s42004-018-0071-6	journal	October 2018
Enhancing catalytic alkane hydroxylation by tuning the outer coordination sphere in a heme-containing metal–organic framework Zee, David Z.; Harris, T. David Chemical Science, Vol. 11, Issue 21 https://doi.org/10.1039/d0sc01796e	journal	January 2020
Hydrophobic Metal–Organic Frameworks Jayaramulu, Kolleboyina; Geyer, Florian; Schneemann, Andreas Advanced Materials https://doi.org/10.1002/adma.201900820	journal	June 2019
Encapsulation of Crabtree's Catalyst in Sulfonated MIL-101(Cr): Enhancement of Stability and Selectivity between Competing Reaction Pathways by the MOF Chemical Microenvironment Grigoropoulos, Alexios; McKay, Alasdair I.; Katsoulidis, Alexandros P. Angewandte Chemie, Vol. 130, Issue 17 https://doi.org/10.1002/ange.201710091	journal	March 2018
Mapping-Out Catalytic Processes in a Metal-Organic Framework with Single-Crystal X-ray Crystallography Burgun, Alexandre; Coghlan, Campbell J.; Huang, David M. Angewandte Chemie International Edition, Vol. 56, Issue 29 https://doi.org/10.1002/anie.201611254	journal	February 2017