Sequential Pore Wall Modification in a Covalent Organic Framework for Application in Lactic Acid Adsorption

Maria S. Lohse; Timothée Stassin; Guillaume Naudin; Stefan Wuttke; Rob Ameloot; Dirk De Vos; Dana D. Medina; Thomas Bein

doi:10.1021/acs.chemmater.5b04388

Sequential Pore Wall Modification in a Covalent Organic Framework for Application in Lactic Acid Adsorption

Maria S. Lohse
, Timothée Stassin
, Guillaume Naudin
, Stefan Wuttke
, Rob Ameloot
, Dirk De Vos
, Dana D. Medina
, Thomas Bein

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

225 Citations (Scopus)

Abstract

Here we describe the synthesis and postsynthetic modification of the stable β-ketoenamine TpBD(NH₂)₂ covalent organic framework (COF), having primary amine groups integrated into the pore walls. For this purpose we initially synthesized the nitro version of this COF, TpBD(NO₂)₂. Afterward, TpBD(NO₂)₂ was reduced to afford the desired framework having primary amine functionality. We demonstrate the accessibility of the primary amine groups and the robustness of the framework by a second modification step, the aminolysis of acetic anhydride, to obtain the corresponding amide form TpBD(NHCOCH₃)₂. Taking advantage of the high stability of these frameworks under acidic conditions, we study the liquid-phase adsorption of lactic acid, revealing the strong impact of a pore wall modification on the adsorption performance.

Original language	English
Pages (from-to)	626-631
Number of pages	6
Journal	Chemistry of Materials
Volume	28
Issue number	2
DOIs	https://doi.org/10.1021/acs.chemmater.5b04388
Publication status	Published - Jan 26 2016
Externally published	Yes

ASJC Scopus subject areas

General Chemistry
General Chemical Engineering
Materials Chemistry

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10.1021/acs.chemmater.5b04388

Cite this

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title = "Sequential Pore Wall Modification in a Covalent Organic Framework for Application in Lactic Acid Adsorption",

abstract = "Here we describe the synthesis and postsynthetic modification of the stable β-ketoenamine TpBD(NH2)2 covalent organic framework (COF), having primary amine groups integrated into the pore walls. For this purpose we initially synthesized the nitro version of this COF, TpBD(NO2)2. Afterward, TpBD(NO2)2 was reduced to afford the desired framework having primary amine functionality. We demonstrate the accessibility of the primary amine groups and the robustness of the framework by a second modification step, the aminolysis of acetic anhydride, to obtain the corresponding amide form TpBD(NHCOCH3)2. Taking advantage of the high stability of these frameworks under acidic conditions, we study the liquid-phase adsorption of lactic acid, revealing the strong impact of a pore wall modification on the adsorption performance.",

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T1 - Sequential Pore Wall Modification in a Covalent Organic Framework for Application in Lactic Acid Adsorption

AU - Lohse, Maria S.

AU - Stassin, Timothée

AU - Naudin, Guillaume

AU - Wuttke, Stefan

AU - Ameloot, Rob

AU - De Vos, Dirk

AU - Medina, Dana D.

AU - Bein, Thomas

PY - 2016/1/26

Y1 - 2016/1/26

N2 - Here we describe the synthesis and postsynthetic modification of the stable β-ketoenamine TpBD(NH2)2 covalent organic framework (COF), having primary amine groups integrated into the pore walls. For this purpose we initially synthesized the nitro version of this COF, TpBD(NO2)2. Afterward, TpBD(NO2)2 was reduced to afford the desired framework having primary amine functionality. We demonstrate the accessibility of the primary amine groups and the robustness of the framework by a second modification step, the aminolysis of acetic anhydride, to obtain the corresponding amide form TpBD(NHCOCH3)2. Taking advantage of the high stability of these frameworks under acidic conditions, we study the liquid-phase adsorption of lactic acid, revealing the strong impact of a pore wall modification on the adsorption performance.

AB - Here we describe the synthesis and postsynthetic modification of the stable β-ketoenamine TpBD(NH2)2 covalent organic framework (COF), having primary amine groups integrated into the pore walls. For this purpose we initially synthesized the nitro version of this COF, TpBD(NO2)2. Afterward, TpBD(NO2)2 was reduced to afford the desired framework having primary amine functionality. We demonstrate the accessibility of the primary amine groups and the robustness of the framework by a second modification step, the aminolysis of acetic anhydride, to obtain the corresponding amide form TpBD(NHCOCH3)2. Taking advantage of the high stability of these frameworks under acidic conditions, we study the liquid-phase adsorption of lactic acid, revealing the strong impact of a pore wall modification on the adsorption performance.

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JO - Chemistry of Materials

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Sequential Pore Wall Modification in a Covalent Organic Framework for Application in Lactic Acid Adsorption

Abstract

ASJC Scopus subject areas

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