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Title: Stable Hydrazone-Linked Covalent Organic Frameworks Containing O,N,O'-Chelating Sites for Fe(III) Detection in Water

Abstract

Two stable crystalline hydrazone-linked covalent organic frameworks (COFs) (Bth-Dha and Bth-Dma) containing functional O,N,O'-chelating sites have been designed and successfully synthesized by the Schiff-base condensation reactions between benzene-1,3,5-tricarbohydrazide (Bth) and 2,5-dihydroxyterephthalaldehyde (Dha) or 2,5-dimethoxyterephthal-aldehyde (Dma), respectively. Bth-Dma exhibits strong fluorescence in the solid state and in an aqueous dispersion, while no fluorescence can be observed for Bth-Dha. Interestingly, the as-synthesized Bth-Dma can be used as a turn-off fluorescence sensor for the Fe(III) ion in aqueous solution with outstanding selectivity and sensitivity. Here, the recognition process can be attributed to the coordination interaction between Fe(III) ion and the O,N,O'-chelating sites in the pore wall of Bth-Dma COF, as verified by X-ray photoelectron spectroscopy and 1H NMR spectroscopy. To the best of our knowledge, this is the first report on the rational design of luminescent COF with predesigned O,N,O'-chelating sites as a fluorescence sensor for highly selective and sensitive metal ion detection. This work may pave the way for designing luminescent COF sensors with functional binding sites for detecting specific metal ions.

Authors:
 [1];  [1]; ORCiD logo [2];  [3];  [4];  [1];  [1]; ORCiD logo [1]; ORCiD logo [4];  [1]
+ Show Author Affiliations
  1. South China Normal Univ., Guangzhou (People's Republic of China)
  2. South China Normal Univ., Guangzhou (People's Republic of China); Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
  3. Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States); China Univ. of Geosciences, Beijing (People's Republic of China)
  4. Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
Publication Date:
Research Org.:
Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES)
OSTI Identifier:
1564022
Grant/Contract Number:  
AC02-05CH11231
Resource Type:
Accepted Manuscript
Journal Name:
ACS Applied Materials and Interfaces
Additional Journal Information:
Journal Volume: 11; Journal Issue: 13; Journal ID: ISSN 1944-8244
Publisher:
American Chemical Society (ACS)
Country of Publication:
United States
Language:
English
Subject:
36 MATERIALS SCIENCE

Citation Formats

Chen, Gui, Lan, Hai-Hang, Cai, Song-Liang, Sun, Bing, Li, Xin-Le, He, Zi-Hao, Zheng, Sheng-Run, Fan, Jun, Liu, Yi, and Zhang, Wei-Guang. Stable Hydrazone-Linked Covalent Organic Frameworks Containing O,N,O'-Chelating Sites for Fe(III) Detection in Water. United States: N. p., 2019. Web. doi:10.1021/acsami.9b02640.
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Chen, Gui, Lan, Hai-Hang, Cai, Song-Liang, Sun, Bing, Li, Xin-Le, He, Zi-Hao, Zheng, Sheng-Run, Fan, Jun, Liu, Yi, & Zhang, Wei-Guang. Stable Hydrazone-Linked Covalent Organic Frameworks Containing O,N,O'-Chelating Sites for Fe(III) Detection in Water. United States. https://doi.org/10.1021/acsami.9b02640
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Chen, Gui, Lan, Hai-Hang, Cai, Song-Liang, Sun, Bing, Li, Xin-Le, He, Zi-Hao, Zheng, Sheng-Run, Fan, Jun, Liu, Yi, and Zhang, Wei-Guang. Wed . "Stable Hydrazone-Linked Covalent Organic Frameworks Containing O,N,O'-Chelating Sites for Fe(III) Detection in Water". United States. https://doi.org/10.1021/acsami.9b02640. https://www.osti.gov/servlets/purl/1564022.
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@article{osti_1564022,
title = {Stable Hydrazone-Linked Covalent Organic Frameworks Containing O,N,O'-Chelating Sites for Fe(III) Detection in Water},
author = {Chen, Gui and Lan, Hai-Hang and Cai, Song-Liang and Sun, Bing and Li, Xin-Le and He, Zi-Hao and Zheng, Sheng-Run and Fan, Jun and Liu, Yi and Zhang, Wei-Guang},
abstractNote = {Two stable crystalline hydrazone-linked covalent organic frameworks (COFs) (Bth-Dha and Bth-Dma) containing functional O,N,O'-chelating sites have been designed and successfully synthesized by the Schiff-base condensation reactions between benzene-1,3,5-tricarbohydrazide (Bth) and 2,5-dihydroxyterephthalaldehyde (Dha) or 2,5-dimethoxyterephthal-aldehyde (Dma), respectively. Bth-Dma exhibits strong fluorescence in the solid state and in an aqueous dispersion, while no fluorescence can be observed for Bth-Dha. Interestingly, the as-synthesized Bth-Dma can be used as a turn-off fluorescence sensor for the Fe(III) ion in aqueous solution with outstanding selectivity and sensitivity. Here, the recognition process can be attributed to the coordination interaction between Fe(III) ion and the O,N,O'-chelating sites in the pore wall of Bth-Dma COF, as verified by X-ray photoelectron spectroscopy and 1H NMR spectroscopy. To the best of our knowledge, this is the first report on the rational design of luminescent COF with predesigned O,N,O'-chelating sites as a fluorescence sensor for highly selective and sensitive metal ion detection. This work may pave the way for designing luminescent COF sensors with functional binding sites for detecting specific metal ions.},
doi = {10.1021/acsami.9b02640},
journal = {ACS Applied Materials and Interfaces},
number = 13,
volume = 11,
place = {United States},
year = {Wed Mar 13 00:00:00 EDT 2019},
month = {Wed Mar 13 00:00:00 EDT 2019}
}
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https://doi.org/10.1021/acsami.9b02640
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Works referenced in this record:

Porous, Crystalline, Covalent Organic Frameworks
journal, November 2005

  • Côté, Adrien P.; Benin, Annabelle I.; Ockwig, Nathan W.
  • Science, Vol. 310, Issue 5751, p. 1166-1170
  • DOI: 10.1126/science.1120411

The atom, the molecule, and the covalent organic framework
journal, March 2017

The Organic Flatland-Recent Advances in Synthetic 2D Organic Layers
journal, March 2015

  • Cai, Song-Liang; Zhang, Wei-Guang; Zuckermann, Ronald N.
  • Advanced Materials, Vol. 27, Issue 38
  • DOI: 10.1002/adma.201500124

Facile transformation of imine covalent organic frameworks into ultrastable crystalline porous aromatic frameworks
journal, July 2018

Exceptional ammonia uptake by a covalent organic framework
journal, February 2010

  • Doonan, Christian J.; Tranchemontagne, David J.; Glover, T. Grant
  • Nature Chemistry, Vol. 2, Issue 3, p. 235-238
  • DOI: 10.1038/nchem.548

Single-Crystal Structure of a Covalent Organic Framework
journal, October 2013

  • Zhang, Yue-Biao; Su, Jie; Furukawa, Hiroyasu
  • Journal of the American Chemical Society, Vol. 135, Issue 44
  • DOI: 10.1021/ja409033p

Mixed Matrix Membranes (MMMs) Comprising Exfoliated 2D Covalent Organic Frameworks (COFs) for Efficient CO 2 Separation
journal, February 2016

3D Porous Crystalline Polyimide Covalent Organic Frameworks for Drug Delivery
journal, June 2015

  • Fang, Qianrong; Wang, Junhua; Gu, Shuang
  • Journal of the American Chemical Society, Vol. 137, Issue 26
  • DOI: 10.1021/jacs.5b04147

Exploiting Noncovalent Interactions in an Imine-Based Covalent Organic Framework for Quercetin Delivery
journal, August 2016

  • Vyas, Vijay S.; Vishwakarma, Medhavi; Moudrakovski, Igor
  • Advanced Materials, Vol. 28, Issue 39
  • DOI: 10.1002/adma.201603006

Construction of Covalent Organic Framework for Catalysis: Pd/COF-LZU1 in Suzuki–Miyaura Coupling Reaction
journal, December 2011

  • Ding, San-Yuan; Gao, Jia; Wang, Qiong
  • Journal of the American Chemical Society, Vol. 133, Issue 49
  • DOI: 10.1021/ja206846p

Chiral Covalent Organic Frameworks with High Chemical Stability for Heterogeneous Asymmetric Catalysis
journal, June 2017

  • Han, Xing; Xia, Qingchun; Huang, Jinjing
  • Journal of the American Chemical Society, Vol. 139, Issue 25
  • DOI: 10.1021/jacs.7b04008

Multivariate Chiral Covalent Organic Frameworks with Controlled Crystallinity and Stability for Asymmetric Catalysis
journal, June 2017

  • Zhang, Jie; Han, Xing; Wu, Xiaowei
  • Journal of the American Chemical Society, Vol. 139, Issue 24
  • DOI: 10.1021/jacs.7b03352

Cationic Covalent Organic Frameworks: A Simple Platform of Anionic Exchange for Porosity Tuning and Proton Conduction
journal, April 2016

  • Ma, Heping; Liu, Bailing; Li, Bin
  • Journal of the American Chemical Society, Vol. 138, Issue 18
  • DOI: 10.1021/jacs.5b13490

Directional Charge-Carrier Transport in Oriented Benzodithiophene Covalent Organic Framework Thin Films
journal, January 2017

  • Medina, Dana D.; Petrus, Michiel L.; Jumabekov, Askhat N.
  • ACS Nano, Vol. 11, Issue 3
  • DOI: 10.1021/acsnano.6b07692

Fluorescence properties and analytical applications of covalent organic frameworks
journal, January 2017

  • Xue, Rui; Guo, Hao; Wang, Ting
  • Analytical Methods, Vol. 9, Issue 25
  • DOI: 10.1039/c7ay01261f

Metal–Organic Framework Materials as Chemical Sensors
journal, September 2011

  • Kreno, Lauren E.; Leong, Kirsty; Farha, Omar K.
  • Chemical Reviews, Vol. 112, Issue 2, p. 1105-1125
  • DOI: 10.1021/cr200324t

An Azine-Linked Covalent Organic Framework
journal, November 2013

  • Dalapati, Sasanka; Jin, Shangbin; Gao, Jia
  • Journal of the American Chemical Society, Vol. 135, Issue 46
  • DOI: 10.1021/ja4103293

A Pyrene-Based, Fluorescent Three-Dimensional Covalent Organic Framework
journal, March 2016

  • Lin, Guiqing; Ding, Huimin; Yuan, Daqiang
  • Journal of the American Chemical Society, Vol. 138, Issue 10
  • DOI: 10.1021/jacs.6b00652

Thioether-Based Fluorescent Covalent Organic Framework for Selective Detection and Facile Removal of Mercury(II)
journal, February 2016

  • Ding, San-Yuan; Dong, Ming; Wang, Ya-Wen
  • Journal of the American Chemical Society, Vol. 138, Issue 9
  • DOI: 10.1021/jacs.5b10754

Exploring fluorescent covalent organic frameworks for selective sensing of Fe3+
journal, May 2018

Ultrathin Two-Dimensional Covalent Organic Framework Nanosheets: Preparation and Application in Highly Sensitive and Selective DNA Detection
journal, June 2017

  • Peng, Yongwu; Huang, Ying; Zhu, Yihan
  • Journal of the American Chemical Society, Vol. 139, Issue 25
  • DOI: 10.1021/jacs.7b04096

Iron(iii) selective molecular and supramolecular fluorescent probes
journal, January 2012

  • Sahoo, Suban K.; Sharma, Darshna; Bera, Rati Kanta
  • Chemical Society Reviews, Vol. 41, Issue 21
  • DOI: 10.1039/c2cs35152h

Fast Response and High Sensitivity Europium Metal Organic Framework Fluorescent Probe with Chelating Terpyridine Sites for Fe 3+
journal, January 2013

  • Zheng, Min; Tan, Huaqiao; Xie, Zhigang
  • ACS Applied Materials & Interfaces, Vol. 5, Issue 3
  • DOI: 10.1021/am302862k

Highly selective sensing of Fe 3+ by an anionic metal–organic framework containing uncoordinated nitrogen and carboxylate oxygen sites
journal, January 2018

  • Chen, Chun-Hui; Wang, Xu-Sheng; Li, Lan
  • Dalton Transactions, Vol. 47, Issue 10
  • DOI: 10.1039/c8dt00088c

Structural studies of Fe(III) and Cu(II) complexes of salycylaldehyde benzoyl hydrazone, a synthetic chelating agent exhibiting diverse biological properties
journal, January 1982

Excited State Luminescence of Multi-(5-phenyl-1,3,4-oxadiazo-2-yl)benzenes in an Electron-Donating Matrix: Exciplex or Electroplex?
journal, December 2009

  • Yang, Chih-Chiang; Hsu, Chia-Jung; Chou, Pi-Tai
  • The Journal of Physical Chemistry B, Vol. 114, Issue 2
  • DOI: 10.1021/jp9093063

Tuneable near white-emissive two-dimensional covalent organic frameworks
journal, June 2018

Homochiral 2D Porous Covalent Organic Frameworks for Heterogeneous Asymmetric Catalysis
journal, September 2016

  • Wang, Xiuren; Han, Xing; Zhang, Jie
  • Journal of the American Chemical Society, Vol. 138, Issue 38
  • DOI: 10.1021/jacs.6b07714

Crystalline Covalent Organic Frameworks with Hydrazone Linkages
journal, August 2011

  • Uribe-Romo, Fernando J.; Doonan, Christian J.; Furukawa, Hiroyasu
  • Journal of the American Chemical Society, Vol. 133, Issue 30, p. 11478-11481
  • DOI: 10.1021/ja204728y

Visible-light-induced photoelectrochemical behaviors of Fe-modified TiO2 nanotube arrays
journal, January 2011

A Luminescent Metal-Organic Framework with Lewis Basic Pyridyl Sites for the Sensing of Metal Ions
journal, January 2009

  • Chen, Banglin; Wang, Liangbo; Xiao, Yunqing
  • Angewandte Chemie International Edition, Vol. 48, Issue 3
  • DOI: 10.1002/anie.200805101
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    Works referencing / citing this record:

    The luminescent and photophysical properties of covalent organic frameworks
    journal, January 2020

    • Haug, W. Karl; Moscarello, Erica M.; Wolfson, Eric R.
    • Chemical Society Reviews, Vol. 49, Issue 3
    • DOI: 10.1039/c9cs00807a

    An unprecedented 2D covalent organic framework with an htb net topology
    journal, January 2019

    • Cai, Song-Liang; He, Zi-Hao; Li, Xin-Le
    • Chemical Communications, Vol. 55, Issue 89
    • DOI: 10.1039/c9cc06780a
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