Please use this identifier to cite or link to this item: https://doi.org/10.1021/jacs.0c00553
Title: Rapid, Scalable Construction of Highly Crystalline Acylhydrazone Two-Dimensional Covalent Organic Frameworks via Dipole-Induced Antiparallel Stacking
Authors: LI XING 
QIAO JINGSI 
CHEE SEE WEE 
XU HAISEN 
ZHAO XIAOXU 
Choi, HS
Yu, W
QUEK SU YING 
UTKUR MIRZIYODOVICH MIRSAIDOV 
LOH KIAN PING 
Issue Date: 11-Mar-2020
Publisher: American Chemical Society (ACS)
Citation: LI XING, QIAO JINGSI, CHEE SEE WEE, XU HAISEN, ZHAO XIAOXU, Choi, HS, Yu, W, QUEK SU YING, UTKUR MIRZIYODOVICH MIRSAIDOV, LOH KIAN PING (2020-03-11). Rapid, Scalable Construction of Highly Crystalline Acylhydrazone Two-Dimensional Covalent Organic Frameworks via Dipole-Induced Antiparallel Stacking. Journal of the American Chemical Society 142 (10) : 4932-4943. ScholarBank@NUS Repository. https://doi.org/10.1021/jacs.0c00553
Abstract: Covalent organic frameworks are an emerging class of porous crystalline organic materials that can be designed and synthesized from the bottom up. Despite progress made in synthesizing COFs of diverse topologies, the synthesis methods are often tedious and unscalable, hampering practical applications. Herein, we demonstrate a scalable, robust method of producing highly crystalline acylhydrazone two-dimensional (2D) COFs with diversified structures (six examples) under open and stirred conditions, with growth typically completed in only 30 min. Our strategy involves selecting molecular building blocks that have bond dipole moments with spatial orientations that favor antiparallel stacking and whose structure allows the restriction of intramolecular bond rotation (RIR) via intra- A nd interlayer hydrogen bonding. This method is widely applicable for hydrazide linkers containing various side-chain functionalities and topicities. By this strategy, the gram-scale synthesis of two highly crystalline COFs (up to 1.4 g yield) was obtained in a one-pot reaction within 30 min.
Source Title: Journal of the American Chemical Society
URI: https://scholarbank.nus.edu.sg/handle/10635/167690
ISSN: 0002-7863
1520-5126
DOI: 10.1021/jacs.0c00553
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