On-surface synthesis of planar dendrimers via divergent cross-coupling reaction

Deng-Yuan Li, Shi-Wen Li, Yu-Li Xie, Xin Hua, Yi-Tao Long, An Wang and Pei-Nian Liu ()
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Deng-Yuan Li: East China University of Science & Technology
Shi-Wen Li: East China University of Science & Technology
Yu-Li Xie: East China University of Science & Technology
Xin Hua: East China University of Science & Technology
Yi-Tao Long: East China University of Science & Technology
An Wang: East China University of Science & Technology
Pei-Nian Liu: East China University of Science & Technology

Nature Communications, 2019, vol. 10, issue 1, 1-9

Abstract: Abstract Dendrimers are homostructural and highly branched macromolecules with unique dendritic effects and extensive use in multidisciplinary fields. Although thousands of dendrimers have been synthesized in solution, the on-surface synthetic protocol for planar dendrimers has never been explored, limiting the elucidation of the mechanism of dendritic effects at the single-molecule level. Herein, we describe an on-surface synthetic approach to planar dendrimers, in which exogenous palladium is used as a catalyst to address the divergent cross-coupling of aryl bromides with isocyanides. This reaction enables one aryl bromide to react with two isocyanides in sequential steps to generate the divergently grown product composed of a core and two branches with high selectivity and reactivity. Then, a dendron with four branches and dendrimers with eight or twelve branches in the outermost shell are synthesized on Au(111). This work opens the door for the on-surface synthesis of various planar dendrimers and relevant macromolecular systems.

Date: 2019
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DOI: 10.1038/s41467-019-10407-6

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