Topotactic Synthesis of Phosphabenzene-Functionalized Porous Organic Polymers: Efficient Ligands in CO2 Conversion
Abstract
Progress toward the preparation of porous organic polymers (POPs) with task-specific functionalities has been exceedingly slow—especially where polymers containing low-oxidation phosphorus in the structure are concerned. In this work, a two-step topotactic pathway for the preparation of phosphabenzene-based POPs (Phos-POPs) under metal-free conditions is reported, without the use of unstable phosphorus-based monomers. The synthetic route allows additional functionalities to be introduced into the porous polymer framework with ease. As an example, partially fluorinated Phos-POPs (F-Phos-POPs) were obtained with a surface area of up to 591 m2 g–1. After coordination with Ru species, a Ru/F-Phos-POPs catalyst exhibited high catalytic efficiency in the formylation of amines (turnover frequency up to 204 h–1) using a CO2/H2 mixture, in comparison with the non-fluorinated analogue (43 h–1) and a Au/TiO2 heterogeneous catalysts reported previously (<44 h–1). This work describes a practical method for synthesis of porous organic phosphorus-based polymers with applications in transition-metal-based heterogeneous catalysis.
- Authors:
-
[1];
[4];
[4];
[1]
- Univ. of Tennessee, Knoxville, TN (United States); Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)
- Univ. of Tennessee, Knoxville, TN (United States)
- Univ. of California, Riverside, CA (United States)
- Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)
- Publication Date:
- Research Org.:
- Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)
- Sponsoring Org.:
- USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences & Biosciences Division
- OSTI Identifier:
- 1808416
- Grant/Contract Number:
- AC05-00OR22725
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Angewandte Chemie (International Edition)
- Additional Journal Information:
- Journal Name: Angewandte Chemie (International Edition); Journal Volume: 58; Journal Issue: 39; Journal ID: ISSN 1433-7851
- Publisher:
- Wiley
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Citation Formats
Yang, Zhenzhen, Chen, Hao, Li, Bo, Guo, Wei, Jie, Kecheng, Sun, Yifan, Jiang, De-en, Popovs, Ilja, and Dai, Sheng. Topotactic Synthesis of Phosphabenzene-Functionalized Porous Organic Polymers: Efficient Ligands in CO2 Conversion. United States: N. p., 2019.
Web. doi:10.1002/anie.201907015.
Yang, Zhenzhen, Chen, Hao, Li, Bo, Guo, Wei, Jie, Kecheng, Sun, Yifan, Jiang, De-en, Popovs, Ilja, & Dai, Sheng. Topotactic Synthesis of Phosphabenzene-Functionalized Porous Organic Polymers: Efficient Ligands in CO2 Conversion. United States. https://doi.org/10.1002/anie.201907015
Yang, Zhenzhen, Chen, Hao, Li, Bo, Guo, Wei, Jie, Kecheng, Sun, Yifan, Jiang, De-en, Popovs, Ilja, and Dai, Sheng. Tue .
"Topotactic Synthesis of Phosphabenzene-Functionalized Porous Organic Polymers: Efficient Ligands in CO2 Conversion". United States. https://doi.org/10.1002/anie.201907015. https://www.osti.gov/servlets/purl/1808416.
@article{osti_1808416,
title = {Topotactic Synthesis of Phosphabenzene-Functionalized Porous Organic Polymers: Efficient Ligands in CO2 Conversion},
author = {Yang, Zhenzhen and Chen, Hao and Li, Bo and Guo, Wei and Jie, Kecheng and Sun, Yifan and Jiang, De-en and Popovs, Ilja and Dai, Sheng},
abstractNote = {Progress toward the preparation of porous organic polymers (POPs) with task-specific functionalities has been exceedingly slow—especially where polymers containing low-oxidation phosphorus in the structure are concerned. In this work, a two-step topotactic pathway for the preparation of phosphabenzene-based POPs (Phos-POPs) under metal-free conditions is reported, without the use of unstable phosphorus-based monomers. The synthetic route allows additional functionalities to be introduced into the porous polymer framework with ease. As an example, partially fluorinated Phos-POPs (F-Phos-POPs) were obtained with a surface area of up to 591 m2 g–1. After coordination with Ru species, a Ru/F-Phos-POPs catalyst exhibited high catalytic efficiency in the formylation of amines (turnover frequency up to 204 h–1) using a CO2/H2 mixture, in comparison with the non-fluorinated analogue (43 h–1) and a Au/TiO2 heterogeneous catalysts reported previously (<44 h–1). This work describes a practical method for synthesis of porous organic phosphorus-based polymers with applications in transition-metal-based heterogeneous catalysis.},
doi = {10.1002/anie.201907015},
journal = {Angewandte Chemie (International Edition)},
number = 39,
volume = 58,
place = {United States},
year = {Tue Jul 16 00:00:00 EDT 2019},
month = {Tue Jul 16 00:00:00 EDT 2019}
}
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Works referenced in this record:
A search for selectivity to enable CO 2 capture with porous adsorbents
journal, January 2018
- Oschatz, M.; Antonietti, M.
- Energy & Environmental Science, Vol. 11, Issue 1
Synthesis of Porous Covalent Quinazoline Networks (CQNs) and Their Gas Sorption Properties
journal, December 2018
- Buyukcakir, Onur; Yuksel, Recep; Jiang, Yi
- Angewandte Chemie International Edition, Vol. 58, Issue 3
Phosphonium salt and ZnX 2 –PPh 3 integrated hierarchical POPs: tailorable synthesis and highly efficient cooperative catalysis in CO 2 utilization
journal, January 2016
- Li, Cunyao; Wang, Wenlong; Yan, Li
- Journal of Materials Chemistry A, Vol. 4, Issue 41
Challenges in the Greener Production of Formates/Formic Acid, Methanol, and DME by Heterogeneously Catalyzed CO 2 Hydrogenation Processes
journal, May 2017
- Álvarez, Andrea; Bansode, Atul; Urakawa, Atsushi
- Chemical Reviews, Vol. 117, Issue 14
π-Conjugated phospholes and their incorporation into devices: components with a great deal of potential
journal, January 2016
- Duffy, M. P.; Delaunay, W.; Bouit, P. -A.
- Chemical Society Reviews, Vol. 45, Issue 19
CO2 capture from humid flue gases and humid atmosphere using a microporous coppersilicate
journal, October 2015
- Datta, S. J.; Khumnoon, C.; Lee, Z. H.
- Science, Vol. 350, Issue 6258
Perfluorinated Covalent Triazine Framework Derived Hybrids for the Highly Selective Electroconversion of Carbon Dioxide into Methane
journal, October 2018
- Wang, Yuanshuang; Chen, Junxiang; Wang, Genxiang
- Angewandte Chemie International Edition, Vol. 57, Issue 40
Organocatalysis in Inert C–H Bond Functionalization
journal, February 2017
- Qin, Yan; Zhu, Lihui; Luo, Sanzhong
- Chemical Reviews, Vol. 117, Issue 13
Phosphine catalysis of allenes with electrophiles
journal, January 2014
- Wang, Zhiming; Xu, Xingzhu; Kwon, Ohyun
- Chem. Soc. Rev., Vol. 43, Issue 9
Übergangsmetall‐ und Organokatalyse: Wo sind Fortschritte zu erwarten?
journal, December 2015
- Zhou, Qi‐Lin
- Angewandte Chemie, Vol. 128, Issue 18
Photoinduced Deaminative Borylation of Alkylamines
journal, July 2018
- Wu, Jingjing; He, Lin; Noble, Adam
- Journal of the American Chemical Society, Vol. 140, Issue 34
Selective Functionalization of Aminoheterocycles by a Pyrylium Salt
journal, July 2018
- Moser, Daniel; Duan, Yaya; Wang, Feng
- Angewandte Chemie, Vol. 130, Issue 34
Palladium/Phosphorus-Doped Porous Organic Polymer as Recyclable Chemoselective and Efficient Hydrogenation Catalyst under Ambient Conditions
journal, June 2017
- Ding, Zong-Cang; Li, Cun-Yao; Chen, Jun-Jia
- Advanced Synthesis & Catalysis, Vol. 359, Issue 13
Hydroxyl Group-Regulated Active Nano-Pd/C Catalyst Generation via in Situ Reduction of Pd(NH 3 ) x Cl y /C for N -Formylation of Amines with CO 2 /H 2
journal, June 2017
- Zhang, Yujing; Wang, Hongli; Yuan, Hangkong
- ACS Sustainable Chemistry & Engineering, Vol. 5, Issue 7
Phosphine-triggered synthesis of functionalized cyclic compounds
journal, January 2008
- Ye, Long-Wu; Zhou, Jian; Tang, Yong
- Chemical Society Reviews, Vol. 37, Issue 6
Amine formylation via carbon dioxide recycling catalyzed by a simple and efficient heterogeneous palladium catalyst
journal, January 2014
- Cui, Xinjiang; Zhang, Yan; Deng, Youquan
- Chem. Commun., Vol. 50, Issue 2
Metalated Mesoporous Poly(triphenylphosphine) with Azo Functionality: Efficient Catalysts for CO 2 Conversion
journal, January 2016
- Yang, Zhenzhen; Yu, Bo; Zhang, Hongye
- ACS Catalysis, Vol. 6, Issue 2
Transition Metal-Catalyzed C–H Amination: Scope, Mechanism, and Applications
journal, January 2017
- Park, Yoonsu; Kim, Youyoung; Chang, Sukbok
- Chemical Reviews, Vol. 117, Issue 13
In Situ Doping Strategy for the Preparation of Conjugated Triazine Frameworks Displaying Efficient CO 2 Capture Performance
journal, September 2016
- Zhu, Xiang; Tian, Chengcheng; Veith, Gabriel M.
- Journal of the American Chemical Society, Vol. 138, Issue 36
Metal-Free Fluorine-Doped Carbon Electrocatalyst for CO 2 Reduction Outcompeting Hydrogen Evolution
journal, April 2018
- Xie, Jiafang; Zhao, Xiaotao; Wu, Maoxiang
- Angewandte Chemie, Vol. 130, Issue 31
Fluoro-functionalized polymeric ionic liquids: highly efficient catalysts for CO 2 cycloaddition to cyclic carbonates under mild conditions
journal, January 2014
- Yang, Zhen-Zhen; Zhao, Yanfei; Ji, Guipeng
- Green Chemistry, Vol. 16, Issue 8
Highly Regio- and Stereoselective Heterogeneous Hydrosilylation of Terminal Alkynes over Cobalt-Metalated Porous Organic Polymer
journal, July 2018
- Li, Ren-Hao; An, Xiao-Ming; Yang, Ying
- Organic Letters, Vol. 20, Issue 16
Microporous Organic Materials for Membrane-Based Gas Separation
journal, October 2017
- Zou, Xiaoqin; Zhu, Guangshan
- Advanced Materials, Vol. 30, Issue 3
Übergangsmetallkatalysierte Carboxylierungen mit Kohlendioxid
journal, October 2018
- Tortajada, Andreu; Juliá‐Hernández, Francisco; Börjesson, Marino
- Angewandte Chemie, Vol. 130, Issue 49
Selective Functionalization of Aminoheterocycles by a Pyrylium Salt
journal, July 2018
- Moser, Daniel; Duan, Yaya; Wang, Feng
- Angewandte Chemie International Edition, Vol. 57, Issue 34
Fluorinated microporous organic polymers: design and applications in CO 2 adsorption and conversion
journal, January 2014
- Yang, Zhen-Zhen; Zhao, Yanfei; Zhang, Hongye
- Chem. Commun., Vol. 50, Issue 90
Global carbon dioxide levels near worrisome milestone
journal, April 2013
- Monastersky, Richard
- Nature, Vol. 497, Issue 7447
Transformation of Carbon Dioxide
journal, June 2007
- Sakakura, Toshiyasu; Choi, Jun-Chul; Yasuda, Hiroyuki
- Chemical Reviews, Vol. 107, Issue 6
Unprecedented high-temperature CO2 selectivity in N2-phobic nanoporous covalent organic polymers
journal, January 2013
- Patel, Hasmukh A.; Hyun Je, Sang; Park, Joonho
- Nature Communications, Vol. 4, Article No. 1357
Perfluorinated Covalent Triazine Framework Derived Hybrids for the Highly Selective Electroconversion of Carbon Dioxide into Methane
journal, September 2018
- Wang, Yuanshuang; Chen, Junxiang; Wang, Genxiang
- Angewandte Chemie, Vol. 130, Issue 40
Metal-Free Fluorine-Doped Carbon Electrocatalyst for CO 2 Reduction Outcompeting Hydrogen Evolution
journal, April 2018
- Xie, Jiafang; Zhao, Xiaotao; Wu, Maoxiang
- Angewandte Chemie International Edition, Vol. 57, Issue 31
Using carbon dioxide as a building block in organic synthesis
journal, January 2015
- Liu, Qiang; Wu, Lipeng; Jackstell, Ralf
- Nature Communications, Vol. 6, Issue 1
A Titanium Dioxide Supported Gold Nanoparticle Catalyst for the Selective N-Formylation of Functionalized Amines with Carbon Dioxide and Hydrogen
journal, August 2017
- Mitsudome, Takato; Urayama, Teppei; Fujita, Shu
- ChemCatChem, Vol. 9, Issue 19
Transition-Metal-Catalyzed Carboxylation Reactions with Carbon Dioxide
journal, October 2018
- Tortajada, Andreu; Juliá-Hernández, Francisco; Börjesson, Marino
- Angewandte Chemie International Edition, Vol. 57, Issue 49
Homogeneous Catalysis for Sustainable Hydrogen Storage in Formic Acid and Alcohols
journal, October 2017
- Sordakis, Katerina; Tang, Conghui; Vogt, Lydia K.
- Chemical Reviews, Vol. 118, Issue 2
Transition-Metal Catalysis and Organocatalysis: Where Can Progress Be Expected?
journal, December 2015
- Zhou, Qi-Lin
- Angewandte Chemie International Edition, Vol. 55, Issue 18
A perfluorinated covalent triazine-based framework for highly selective and water–tolerant CO2 capture
journal, January 2013
- Zhao, Yunfeng; Yao, Ke Xin; Teng, Baiyang
- Energy & Environmental Science, Vol. 6, Issue 12
Mesoporous imine-based organic polymer: catalyst-free synthesis in water and application in CO 2 conversion
journal, January 2018
- Yu, Xiaoxiao; Yang, Zhenzhen; Guo, Shien
- Chemical Communications, Vol. 54, Issue 55
N -Formylation of Amines with CO 2 and H 2 Using Pd–Au Bimetallic Catalysts Supported on Polyaniline-Functionalized Carbon Nanotubes
journal, February 2017
- Ju, Pengpeng; Chen, Jinzhu; Chen, Aibing
- ACS Sustainable Chemistry & Engineering, Vol. 5, Issue 3
Preparation of polyphosphazenes: a tutorial review
journal, January 2016
- Rothemund, Sandra; Teasdale, Ian
- Chemical Society Reviews, Vol. 45, Issue 19
Recent advances in well-defined, late transition metal complexes that make and/or break C–N, C–O and C–S bonds
journal, January 2017
- Desnoyer, Addison N.; Love, Jennifer A.
- Chemical Society Reviews, Vol. 46, Issue 1
Visible-Light-Promoted [2 + 2 + 2] Cyclization of Alkynes with Nitriles to Pyridines Using Pyrylium Salts as Photoredox Catalysts
journal, April 2017
- Wang, Kuai; Meng, Ling-Guo; Wang, Lei
- Organic Letters, Vol. 19, Issue 8
Highly Efficient Heterogeneous Hydroformylation over Rh-Metalated Porous Organic Polymers: Synergistic Effect of High Ligand Concentration and Flexible Framework
journal, April 2015
- Sun, Qi; Dai, Zhifeng; Liu, Xiaolong
- Journal of the American Chemical Society, Vol. 137, Issue 15
Phosphabenzenes as Monodentate π-Acceptor Ligands for Rhodium-Catalyzed Hydroformylation
journal, July 2001
- Breit, Bernhard; Winde, Roland; Mackewitz, Thomas
- Chemistry - A European Journal, Vol. 7, Issue 14
Pyridine-functionalized organic porous polymers: applications in efficient CO 2 adsorption and conversion
journal, January 2017
- Yang, Zhenzhen; Wang, Huan; Ji, Guipeng
- New Journal of Chemistry, Vol. 41, Issue 8
Ruthenium Metal-Organic Frameworks with Different Defect Types: Influence on Porosity, Sorption, and Catalytic Properties
journal, August 2016
- Zhang, Wenhua; Kauer, Max; Halbherr, Olesia
- Chemistry - A European Journal, Vol. 22, Issue 40
Synthesis of Porous Covalent Quinazoline Networks (CQNs) and Their Gas Sorption Properties
journal, December 2018
- Buyukcakir, Onur; Yuksel, Recep; Jiang, Yi
- Angewandte Chemie
Transformation of Carbon Dioxide
journal, September 2007
- Sakakura, Toshiyasu; Choi, Jun-Chul; Yasuda, Hiroyuki
- ChemInform, Vol. 38, Issue 36
Works referencing / citing this record:
A succinct strategy for construction of nanoporous ionic organic networks from a pyrylium intermediate
journal, January 2019
- Che, Siying; Yang, Zhenzhen; Popovs, Ilja
- Chemical Communications, Vol. 55, Issue 89