Highly Stable Single Crystals of Three-Dimensional Porous Oligomer Frameworks Synthesized under Kinetic Conditions

Linxiao Hou; Chuan Shan; Yanpei Song; Sifan Chen; Lukasz Wojtas; Shengqian Ma; Qi Sun; Lin Zhang

doi:10.1002/anie.202103729

Highly Stable Single Crystals of Three-Dimensional Porous Oligomer Frameworks Synthesized under Kinetic Conditions

Linxiao Hou, Chuan Shan, Yanpei Song, Sifan Chen, Lukasz Wojtas, Shengqian Ma, Qi Sun, Lin Zhang

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

27 Scopus citations

Abstract

Various robust, crystalline, and porous organic frameworks based on in situ-formed imine-linked oligomers were investigated. These oligomers self-assembled through collaborative intermolecular hydrogen bonding interactions via liquid–liquid interfacial reactions. The soluble oligomers were kinetic products with multiple unreacted aldehyde groups that acted as hydrogen bond donors and acceptors and directed the assembly of the resulting oligomers into 3D frameworks. The sequential formation of robust covalent linkages and highly reversible hydrogen bonds enforced long-range symmetry and facilitated the production of large single crystals, with structures that were unambiguously determined by single-crystal X-ray diffraction. The unique hierarchical arrangements increased the steric hindrance of the imine bond, which prevented attacks from water molecules, greatly improving the stability. The multiple binding sites in the frameworks enabled rapid sequestration of micropollutant in water.

Original language	English
Pages (from-to)	14664-14670
Number of pages	7
Journal	Angewandte Chemie - International Edition
Volume	60
Issue number	26
DOIs	https://doi.org/10.1002/anie.202103729
State	Published - Jun 21 2021
Externally published	Yes

Funding

The authors acknowledge the National Science Foundation of China (21776241, 2196116074, 22072132) and the Fundamental Research Funds for the Central Universities (2019XZZX003‐04, 17221012001) for financial support of this work. Partial support from the U.S. National Science Foundation (CBET‐1706025) and the Robert A. Welch Foundation (B‐0027) is also acknowledged.

Funders	Funder number
National Science Foundation	CBET‐1706025
Welch Foundation	B‐0027
National Natural Science Foundation of China	22072132, 2196116074, 21776241
Fundamental Research Funds for the Central Universities	2019XZZX003‐04, 17221012001

Keywords

hydrolytic stability
interfacial polymerization
kinetic conditions
micropollutant removal
porous organic crystals

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10.1002/anie.202103729

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title = "Highly Stable Single Crystals of Three-Dimensional Porous Oligomer Frameworks Synthesized under Kinetic Conditions",

abstract = "Various robust, crystalline, and porous organic frameworks based on in situ-formed imine-linked oligomers were investigated. These oligomers self-assembled through collaborative intermolecular hydrogen bonding interactions via liquid–liquid interfacial reactions. The soluble oligomers were kinetic products with multiple unreacted aldehyde groups that acted as hydrogen bond donors and acceptors and directed the assembly of the resulting oligomers into 3D frameworks. The sequential formation of robust covalent linkages and highly reversible hydrogen bonds enforced long-range symmetry and facilitated the production of large single crystals, with structures that were unambiguously determined by single-crystal X-ray diffraction. The unique hierarchical arrangements increased the steric hindrance of the imine bond, which prevented attacks from water molecules, greatly improving the stability. The multiple binding sites in the frameworks enabled rapid sequestration of micropollutant in water.",

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author = "Linxiao Hou and Chuan Shan and Yanpei Song and Sifan Chen and Lukasz Wojtas and Shengqian Ma and Qi Sun and Lin Zhang",

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T1 - Highly Stable Single Crystals of Three-Dimensional Porous Oligomer Frameworks Synthesized under Kinetic Conditions

AU - Hou, Linxiao

AU - Shan, Chuan

AU - Song, Yanpei

AU - Chen, Sifan

AU - Wojtas, Lukasz

AU - Ma, Shengqian

AU - Sun, Qi

AU - Zhang, Lin

PY - 2021/6/21

Y1 - 2021/6/21

N2 - Various robust, crystalline, and porous organic frameworks based on in situ-formed imine-linked oligomers were investigated. These oligomers self-assembled through collaborative intermolecular hydrogen bonding interactions via liquid–liquid interfacial reactions. The soluble oligomers were kinetic products with multiple unreacted aldehyde groups that acted as hydrogen bond donors and acceptors and directed the assembly of the resulting oligomers into 3D frameworks. The sequential formation of robust covalent linkages and highly reversible hydrogen bonds enforced long-range symmetry and facilitated the production of large single crystals, with structures that were unambiguously determined by single-crystal X-ray diffraction. The unique hierarchical arrangements increased the steric hindrance of the imine bond, which prevented attacks from water molecules, greatly improving the stability. The multiple binding sites in the frameworks enabled rapid sequestration of micropollutant in water.

AB - Various robust, crystalline, and porous organic frameworks based on in situ-formed imine-linked oligomers were investigated. These oligomers self-assembled through collaborative intermolecular hydrogen bonding interactions via liquid–liquid interfacial reactions. The soluble oligomers were kinetic products with multiple unreacted aldehyde groups that acted as hydrogen bond donors and acceptors and directed the assembly of the resulting oligomers into 3D frameworks. The sequential formation of robust covalent linkages and highly reversible hydrogen bonds enforced long-range symmetry and facilitated the production of large single crystals, with structures that were unambiguously determined by single-crystal X-ray diffraction. The unique hierarchical arrangements increased the steric hindrance of the imine bond, which prevented attacks from water molecules, greatly improving the stability. The multiple binding sites in the frameworks enabled rapid sequestration of micropollutant in water.

KW - hydrolytic stability

KW - interfacial polymerization

KW - kinetic conditions

KW - micropollutant removal

KW - porous organic crystals

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U2 - 10.1002/anie.202103729

DO - 10.1002/anie.202103729

M3 - Article

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AN - SCOPUS:85106754177

SN - 1433-7851

VL - 60

SP - 14664

EP - 14670

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 26

ER -

Highly Stable Single Crystals of Three-Dimensional Porous Oligomer Frameworks Synthesized under Kinetic Conditions

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Keywords

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