Cyclophane-based two-dimensional polymer formed by an interfacial click reaction

Indranil Roy; Austin M. Evans; Partha Jyoti Das; Mohamed Ateia; Matthew R. Ryder; Leighton O. Jones; Masoud Kazem-Rostami; Subhadip Goswami; Yassine Beldjoudi; Dengke Shen; George C. Schatz; Joseph T. Hupp; William R. Dichtel; J. Fraser Stoddart

doi:10.1016/j.xcrp.2022.100806

Cyclophane-based two-dimensional polymer formed by an interfacial click reaction

Indranil Roy, Austin M. Evans, Partha Jyoti Das, Mohamed Ateia, Matthew R. Ryder, Leighton O. Jones, Masoud Kazem-Rostami, Subhadip Goswami, Yassine Beldjoudi, Dengke Shen, George C. Schatz, Joseph T. Hupp, William R. Dichtel, J. Fraser Stoddart^*

^*Corresponding author for this work

Chemistry

Research output: Contribution to journal › Article › peer-review

3 Scopus citations

Abstract

Two-dimensional polymers (2DPs) that incorporate molecular hosts offer a distinctive combination of properties, including covalent connectivity, structural regularity, chemical stability, permanent porosity, and molecular recognition. These features make these topologically planar macromolecular sheets promising in relation to applications, including those that appear in sensors, organic electronics, and nanofiltration membranes. Here, we use copper-catalyzed azide-alkyne click chemistry to construct a cyclophane-based 2DP at a liquid-liquid interface by polymerizing a bisazide-functionalized tetracationic cyclophane monomer with a 1,3,5-triethynylbenzene node. The 2DP prepared by employing this strategy is observed to be crystalline porous sheets by a combination of synchrotron X-ray diffraction, transmission electron microscopy, electron diffraction, and nitrogen porosimetry. When employed as the active layer in nanofiltration membranes, this 2DP exhibits excellent rejection performance of a dye, Brilliant Blue G, with 99% of the dye being removed after each cycle. Our findings could lead to the broad application of interfacial click polymerizations to produce 2DPs.

Original language	English (US)
Article number	100806
Journal	Cell Reports Physical Science
Volume	3
Issue number	4
DOIs	https://doi.org/10.1016/j.xcrp.2022.100806
State	Published - Apr 20 2022

Keywords

CuAAC polymerization
cyclophane
cyclophane-based polymer
host molecule
interfacial click reaction
interfacial polymerization
membrane
nanofiltration
two-dimensional polymers
water purification

ASJC Scopus subject areas

Chemistry(all)
Materials Science(all)
Engineering(all)
Energy(all)
Physics and Astronomy(all)

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10.1016/j.xcrp.2022.100806

Cite this

Roy, I., Evans, A. M., Das, P. J., Ateia, M., Ryder, M. R., Jones, L. O., Kazem-Rostami, M., Goswami, S., Beldjoudi, Y., Shen, D., Schatz, G. C., Hupp, J. T., Dichtel, W. R., & Stoddart, J. F. (2022). Cyclophane-based two-dimensional polymer formed by an interfacial click reaction. Cell Reports Physical Science, 3(4), Article 100806. https://doi.org/10.1016/j.xcrp.2022.100806

@article{3c85f10c18fd4a61a3d6615f2a44d8c4,

title = "Cyclophane-based two-dimensional polymer formed by an interfacial click reaction",

abstract = "Two-dimensional polymers (2DPs) that incorporate molecular hosts offer a distinctive combination of properties, including covalent connectivity, structural regularity, chemical stability, permanent porosity, and molecular recognition. These features make these topologically planar macromolecular sheets promising in relation to applications, including those that appear in sensors, organic electronics, and nanofiltration membranes. Here, we use copper-catalyzed azide-alkyne click chemistry to construct a cyclophane-based 2DP at a liquid-liquid interface by polymerizing a bisazide-functionalized tetracationic cyclophane monomer with a 1,3,5-triethynylbenzene node. The 2DP prepared by employing this strategy is observed to be crystalline porous sheets by a combination of synchrotron X-ray diffraction, transmission electron microscopy, electron diffraction, and nitrogen porosimetry. When employed as the active layer in nanofiltration membranes, this 2DP exhibits excellent rejection performance of a dye, Brilliant Blue G, with 99% of the dye being removed after each cycle. Our findings could lead to the broad application of interfacial click polymerizations to produce 2DPs.",

keywords = "CuAAC polymerization, cyclophane, cyclophane-based polymer, host molecule, interfacial click reaction, interfacial polymerization, membrane, nanofiltration, two-dimensional polymers, water purification",

author = "Indranil Roy and Evans, {Austin M.} and Das, {Partha Jyoti} and Mohamed Ateia and Ryder, {Matthew R.} and Jones, {Leighton O.} and Masoud Kazem-Rostami and Subhadip Goswami and Yassine Beldjoudi and Dengke Shen and Schatz, {George C.} and Hupp, {Joseph T.} and Dichtel, {William R.} and Stoddart, {J. Fraser}",

note = "Funding Information: The authors would like to thank Northwestern University for their continued support of this research. A.M.E. ( DGE-1324585 ) is supported by the National Science Foundation Graduate Research Fellowship. J.T.H. acknowledges support from the US Department of Energy (DOE), Office of Science, Basic Energy Sciences via grant DE-FG02-08ER15967 . L.O.J. and G.C.S. were supported by the Center for the Sustainable Separation of Metals funded by the National Science Foundation (grant no. CHE1925708 ). Portions of this work were performed at the DND-CAT located at Sector 5 and Sector 8 of the APS. This research used resources of the Advanced Photon Source (APS) and Center for Nanoscale Materials, both US DOE Office of Science User Facilities operated for the DOE Office of Science by Argonne National Laboratory under contract DE-AC02-06CH11357, and the National Energy Research Scientific Computing Center, a DOE Office of Science User Facility supported by the Office of Science of the US DOE under contract no. DE-AC02-05CH11231. Resources at the APS were funded by the National Science Foundation under award 0960140. Funding Information: The authors would like to thank Northwestern University for their continued support of this research. A.M.E. (DGE-1324585) is supported by the National Science Foundation Graduate Research Fellowship. J.T.H. acknowledges support from the US Department of Energy (DOE), Office of Science, Basic Energy Sciences via grant DE-FG02-08ER15967. L.O.J. and G.C.S. were supported by the Center for the Sustainable Separation of Metals funded by the National Science Foundation (grant no. CHE1925708). Portions of this work were performed at the DND-CAT located at Sector 5 and Sector 8 of the APS. This research used resources of the Advanced Photon Source (APS) and Center for Nanoscale Materials, both US DOE Office of Science User Facilities operated for the DOE Office of Science by Argonne National Laboratory under contract DE-AC02-06CH11357, and the National Energy Research Scientific Computing Center, a DOE Office of Science User Facility supported by the Office of Science of the US DOE under contract no. DE-AC02-05CH11231. Resources at the APS were funded by the National Science Foundation under award 0960140. I.R. and J.F.S. conceived the project. I.R. A.M.E. M.A. and J.F.S. prepared the manuscript. I.R. synthesized and characterized the compounds. A.M.E. performed the synchrotron X-ray crystallographic experiments. Y.B. performed single-crystal XRD experiments. I.R. and D.S. performed TEM experiments. S.G. carried out nitrogen sorption and electrochemical experiments. M.R.R. and L.O.J. performed computational studies. I.R. and M.A. performed dye-rejection experiments. All other co-authors contributed to various stages of manuscript preparation. The authors declare no competing interests. Publisher Copyright: {\textcopyright} 2022 The Author(s)",

year = "2022",

month = apr,

day = "20",

doi = "10.1016/j.xcrp.2022.100806",

language = "English (US)",

volume = "3",

journal = "Cell Reports Physical Science",

issn = "2666-3864",

publisher = "Cell Press",

number = "4",

}

TY - JOUR

T1 - Cyclophane-based two-dimensional polymer formed by an interfacial click reaction

AU - Roy, Indranil

AU - Evans, Austin M.

AU - Das, Partha Jyoti

AU - Ateia, Mohamed

AU - Ryder, Matthew R.

AU - Jones, Leighton O.

AU - Kazem-Rostami, Masoud

AU - Goswami, Subhadip

AU - Beldjoudi, Yassine

AU - Shen, Dengke

AU - Schatz, George C.

AU - Hupp, Joseph T.

AU - Dichtel, William R.

AU - Stoddart, J. Fraser

N1 - Funding Information: The authors would like to thank Northwestern University for their continued support of this research. A.M.E. ( DGE-1324585 ) is supported by the National Science Foundation Graduate Research Fellowship. J.T.H. acknowledges support from the US Department of Energy (DOE), Office of Science, Basic Energy Sciences via grant DE-FG02-08ER15967 . L.O.J. and G.C.S. were supported by the Center for the Sustainable Separation of Metals funded by the National Science Foundation (grant no. CHE1925708 ). Portions of this work were performed at the DND-CAT located at Sector 5 and Sector 8 of the APS. This research used resources of the Advanced Photon Source (APS) and Center for Nanoscale Materials, both US DOE Office of Science User Facilities operated for the DOE Office of Science by Argonne National Laboratory under contract DE-AC02-06CH11357, and the National Energy Research Scientific Computing Center, a DOE Office of Science User Facility supported by the Office of Science of the US DOE under contract no. DE-AC02-05CH11231. Resources at the APS were funded by the National Science Foundation under award 0960140. Funding Information: The authors would like to thank Northwestern University for their continued support of this research. A.M.E. (DGE-1324585) is supported by the National Science Foundation Graduate Research Fellowship. J.T.H. acknowledges support from the US Department of Energy (DOE), Office of Science, Basic Energy Sciences via grant DE-FG02-08ER15967. L.O.J. and G.C.S. were supported by the Center for the Sustainable Separation of Metals funded by the National Science Foundation (grant no. CHE1925708). Portions of this work were performed at the DND-CAT located at Sector 5 and Sector 8 of the APS. This research used resources of the Advanced Photon Source (APS) and Center for Nanoscale Materials, both US DOE Office of Science User Facilities operated for the DOE Office of Science by Argonne National Laboratory under contract DE-AC02-06CH11357, and the National Energy Research Scientific Computing Center, a DOE Office of Science User Facility supported by the Office of Science of the US DOE under contract no. DE-AC02-05CH11231. Resources at the APS were funded by the National Science Foundation under award 0960140. I.R. and J.F.S. conceived the project. I.R. A.M.E. M.A. and J.F.S. prepared the manuscript. I.R. synthesized and characterized the compounds. A.M.E. performed the synchrotron X-ray crystallographic experiments. Y.B. performed single-crystal XRD experiments. I.R. and D.S. performed TEM experiments. S.G. carried out nitrogen sorption and electrochemical experiments. M.R.R. and L.O.J. performed computational studies. I.R. and M.A. performed dye-rejection experiments. All other co-authors contributed to various stages of manuscript preparation. The authors declare no competing interests. Publisher Copyright: © 2022 The Author(s)

PY - 2022/4/20

Y1 - 2022/4/20

N2 - Two-dimensional polymers (2DPs) that incorporate molecular hosts offer a distinctive combination of properties, including covalent connectivity, structural regularity, chemical stability, permanent porosity, and molecular recognition. These features make these topologically planar macromolecular sheets promising in relation to applications, including those that appear in sensors, organic electronics, and nanofiltration membranes. Here, we use copper-catalyzed azide-alkyne click chemistry to construct a cyclophane-based 2DP at a liquid-liquid interface by polymerizing a bisazide-functionalized tetracationic cyclophane monomer with a 1,3,5-triethynylbenzene node. The 2DP prepared by employing this strategy is observed to be crystalline porous sheets by a combination of synchrotron X-ray diffraction, transmission electron microscopy, electron diffraction, and nitrogen porosimetry. When employed as the active layer in nanofiltration membranes, this 2DP exhibits excellent rejection performance of a dye, Brilliant Blue G, with 99% of the dye being removed after each cycle. Our findings could lead to the broad application of interfacial click polymerizations to produce 2DPs.

AB - Two-dimensional polymers (2DPs) that incorporate molecular hosts offer a distinctive combination of properties, including covalent connectivity, structural regularity, chemical stability, permanent porosity, and molecular recognition. These features make these topologically planar macromolecular sheets promising in relation to applications, including those that appear in sensors, organic electronics, and nanofiltration membranes. Here, we use copper-catalyzed azide-alkyne click chemistry to construct a cyclophane-based 2DP at a liquid-liquid interface by polymerizing a bisazide-functionalized tetracationic cyclophane monomer with a 1,3,5-triethynylbenzene node. The 2DP prepared by employing this strategy is observed to be crystalline porous sheets by a combination of synchrotron X-ray diffraction, transmission electron microscopy, electron diffraction, and nitrogen porosimetry. When employed as the active layer in nanofiltration membranes, this 2DP exhibits excellent rejection performance of a dye, Brilliant Blue G, with 99% of the dye being removed after each cycle. Our findings could lead to the broad application of interfacial click polymerizations to produce 2DPs.

KW - CuAAC polymerization

KW - cyclophane

KW - cyclophane-based polymer

KW - host molecule

KW - interfacial click reaction

KW - interfacial polymerization

KW - membrane

KW - nanofiltration

KW - two-dimensional polymers

KW - water purification

UR - http://www.scopus.com/inward/record.url?scp=85127462167&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85127462167&partnerID=8YFLogxK

U2 - 10.1016/j.xcrp.2022.100806

DO - 10.1016/j.xcrp.2022.100806

M3 - Article

AN - SCOPUS:85127462167

SN - 2666-3864

VL - 3

JO - Cell Reports Physical Science

JF - Cell Reports Physical Science

IS - 4

M1 - 100806

ER -

Cyclophane-based two-dimensional polymer formed by an interfacial click reaction

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Keywords

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