J. Am. Chem. Soc.: Two-Dimensional Chirality Transfer via On-Surface Reaction

Date:2016-04-10Keywords:Two-dimensional chirality transferView:478


Two-Dimensional Chirality Transfer via On-Surface Reaction


Haiming Zhang, Zhongmiao Gong, Kewei Sun, Ruomeng Duan, Penghui Ji, Ling Li, Chen Li, Klaus Müllen, and Lifeng Chi*


1Institute of Functional Nano&Soft Materials (FUNSOM), Jiangsu Key Laboratory for Carbon-Based Functional Materials & Devices, Soochow University, 199 Ren’ai Road, Suzhou, Jiangsu 215123, People’s Republic of China 

2Max Planck Institute for Polymer Research, Ackermannweg 10, D-55128 Mainz, Germany 

 3Institute of Physical Chemistry, Johannes Gutenberg University Mainz, Duesbergweg 10-14, D-55128 Mainz, Germany


Two-dimensional chirality transfer from selfassembled (SA) molecules to covalently bonded products was achieved via on-surface synthesis on Au(111) substrates by choosing 1,4-dibromo-2,5-didodecylbenzene (12DB) and 1,4- dibromo-2,5-ditridecylbenzene (13DB) as designed precursors. Scanning tunneling microscopy investigations reveal that their aryl−aryl coupling reaction occurs by connecting the nearest neighboring precursors and thus preserving the SA lamellar structure. The SA structures of 12(13)DB precursors determine the final structures of produced oligo-p-phenylenes (OPP) on the surface. Pure homochiral domains (12DB) give rise to homochiral domains of OPP, whereas lamellae containing mixed chiral geometry of the precursor (13DB) results in the formation of racemic lamellae of OPP.