Separation of Arylenevinylene Macrocycles with a Surface-Confined Two-Dimensional Covalent Organic Framework.

Angew Chem Int Ed Engl

Tianjin Key Laboratory of Molecular Optoelectronic Science, Department of Chemistry, School of Science & Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin University, Tianjin, 300072, P. R. China.

Published: July 2018

A two-dimensional surface covalent organic framework, prepared by a surface-confined synthesis using 4,4'-azodianiline and benzene-1,3,5-tricarbaldehyde as the precursors, was used as a host network to effectively immobilize arylenevinylene macrocycles (AVMs). Thus AVMs could be separated from their linear polymer analogues, which are the common side-products in the cyclooligomerization process. Scanning tunneling microscopy investigations revealed efficient removal of linear polymers by a simple surface binding and solvent washing process.

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http://dx.doi.org/10.1002/anie.201803937DOI Listing

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Separation of Arylenevinylene Macrocycles with a Surface-Confined Two-Dimensional Covalent Organic Framework.

Angew Chem Int Ed Engl

July 2018

Tianjin Key Laboratory of Molecular Optoelectronic Science, Department of Chemistry, School of Science & Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin University, Tianjin, 300072, P. R. China.

A two-dimensional surface covalent organic framework, prepared by a surface-confined synthesis using 4,4'-azodianiline and benzene-1,3,5-tricarbaldehyde as the precursors, was used as a host network to effectively immobilize arylenevinylene macrocycles (AVMs). Thus AVMs could be separated from their linear polymer analogues, which are the common side-products in the cyclooligomerization process. Scanning tunneling microscopy investigations revealed efficient removal of linear polymers by a simple surface binding and solvent washing process.

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Shape-persistent arylenevinylene macrocycles (AVMs) were successfully prepared in one step from readily available aromatic diene monomers through olefin metathesis in good yields. (1)H NMR, UV-Vis absorption and fluorescence studies revealed the aggregation behavior of the obtained macrocycles. SEM characterization showed AVM nanofibril formation.

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