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Main Title: Vinylene-Linked Covalent Organic Frameworks by Base-Catalyzed Aldol Condensation
Author(s): Acharjya, Amitava
Pachfule, Pradip
Roeser, Jérôme
Schmitt, Franz-Josef
Thomas, Arne
Type: Article
Language Code: en
Abstract: Two 2D covalent organic frameworks (COFs) linked by vinylene (−CH=CH−) groups (V‐COF‐1 and V‐COF‐2) are synthesized by exploiting the electron deficient nature of the aromatic s‐triazine unit of C3‐symmetric 2,4,6‐trimethyl‐s‐triazine (TMT). The acidic terminal methyl hydrogens of TMT can easily be abstracted by a base, resulting in a stabilized carbanion, which further undergoes aldol condensation with multitopic aryl aldehydes to be reticulated into extended crystalline frameworks (V‐COFs). Both V‐COF‐1 (with terepthalaldehyde (TA)) and V‐COF‐2 (with 1,3,5‐tris(p‐formylphenyl)benzene (TFPB)) are polycrystalline and exhibit permanent porosity and BET surface areas of 1341 m2 g−1 and 627 m2 g−1, respectively. Owing to the close proximity (3.52 Å) of the pre‐organized vinylene linkages within adjacent 2D layers stacked in eclipsed fashion, [2+2] photo‐cycloadditon in V‐COF‐1 formed covalent crosslinks between the COF layers.
Issue Date: 9-Sep-2019
Date Available: 13-Feb-2020
DDC Class: 540 Chemie und zugeordnete Wissenschaften
Subject(s): covalent organic frameworks
[2+ +2] cycloaddition
porous polymers
vinylene links
Sponsor/Funder: TU Berlin, Open-Access-Mittel - 2019
DFG, 390540038, EXC 2008: UniSysCat
Journal Title: Angewandte Chemie International Edition
Publisher: Wiley
Publisher Place: Weinheim
Volume: 58
Issue: 42
Publisher DOI: 10.1002/anie.201905886
Page Start: 14865
Page End: 14870
EISSN: 1521-3773
ISSN: 1433-7851
Appears in Collections:FG Funktionsmaterialien » Publications

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