Bottom-Up Synthesis of Heteroatom-Doped Chiral Graphene Nanoribbons

Wang, Xiao-Ye; Urgel, José I.; Barin, Gabriela Borin; Eimre, Kristjan; Di Giovannantonio, Marco; Milani, Alberto; Tommasini, Matteo; Pignedoli, Carlo A.; Ruffieux, Pascal; Feng, Xinliang; Fasel, Roman; Müllen, Klaus; Narita, Akimitsu (2018). Bottom-Up Synthesis of Heteroatom-Doped Chiral Graphene Nanoribbons. Journal of the American Chemical Society, 140(29), pp. 9104-9107. American Chemical Society 10.1021/jacs.8b06210

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Bottom-up synthesis of graphene nanoribbons (GNRs) has significantly advanced during the past decade, providing various GNR structures with tunable properties. The synthesis of chiral GNRs, however, has been underexplored and only limited to (3,1)-GNRs. We report herein the surface-assisted synthesis of the first heteroatom-doped chiral (4,1)-GNRs from the rationally designed precursor 6,16-dibromo-9,10,19,20-tetraoxa-9a,19a-diboratetrabenzo[a,f,j,o]perylene. The structure of the chiral GNRs has been verified by scanning tunneling microscopy, noncontact atomic force microscopy, and Raman spectroscopy in combination with theoretical modeling. Due to the presence of oxygen–boron–oxygen (OBO) segments on the edges, lateral self-assembly of the GNRs has been observed, realizing well-aligned GNR arrays with different modes of homochiral and heterochiral inter-ribbon assemblies.

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