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Stepwise on-surface dissymmetric reaction to construct binodal organometallic network

Dissymmetric reactions, which enable differentiated functionalization of equivalent sites within one molecule, have many potential applications in synthetic chemistry and materials science, but they are very challenging to achieve. Here, the dissymmetric reaction of 1,4-dibromo-2,5-diethynylbenzene...

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Bibliographic Details
Published in:Nature communications 2019-06, Vol.10 (1), p.2545-10, Article 2545
Main Authors: Liu, Jing, Chen, Qiwei, Cai, Kang, Li, Jie, Li, Yaru, Yang, Xiao, Zhang, Yajie, Wang, Yongfeng, Tang, Hao, Zhao, Dahui, Wu, Kai
Format: Article
Language:English
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Summary:Dissymmetric reactions, which enable differentiated functionalization of equivalent sites within one molecule, have many potential applications in synthetic chemistry and materials science, but they are very challenging to achieve. Here, the dissymmetric reaction of 1,4-dibromo-2,5-diethynylbenzene (2Br-DEB) on Ag(111) is realized by using a stepwise activation strategy, leading to an ordered two-dimensional organometallic network containing both alkynyl–silver–alkynyl and alkynyl–silver–phenyl nodes. Scanning tunneling microscopy and density functional theory calculations are employed to explore the stepwise conversion of 2Br-DEB, which starts from the H-passivation of one Br-substituted site at 300 K in accompaniment with an intermolecular reaction to form one-dimensional organometallic chains containing alkynyl–silver–alkynyl nodes. Afterwards, the other equivalent Br-substituted site undergoes metalation reaction at 320–450 K, resulting in transformation of the chains into the binodal networks. These findings exemplify the achievement of the dissymmetric reaction and its practical application for controlled fabrications of complicated yet ordered nanostructures on a surface. Dissymmetric functionalization of equivalent sites in a molecule is a synthetic challenge. Here, the authors achieve an on-surface dissymmetric reaction of a molecular precursor through stepwise activation of its identical functional groups, leading to the formation of a 2D organometallic network with two types of nodes.
ISSN:2041-1723
2041-1723
DOI:10.1038/s41467-019-10522-4