首页|On-surface Synthesis of Multiple Non-benzenoid Carbohelicenes Fused with Fluorene Unit(s)

On-surface Synthesis of Multiple Non-benzenoid Carbohelicenes Fused with Fluorene Unit(s)

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Carbohelicenes have garnered considerable attention for their inherent chirality and structural flexibility.Increasing multi-helicity and incorporating non-six-membered rings to substitute benzenoid rings within helicenes are effective strategies for introducing unique photoelectric properties.Despite the disclosure of numerous helicenes,the inaccessible precursors and the lack of synthetic routes pose a challenge in achieving desired helicene structures fused with non-benzenoid rings.Herein,we report the synthesis of multiple non-benzenoid carbohelicenes fused with fluorene unit(s)through intramolecular cyclodehydrogenation of 9,10-di(naphthalen-1-yl)anthracene on Au(111)surface.Two potential cyclodehydrogenation manners between naphthyl and anthracene lead to the for-mation of fluorene-fused[5]helicene and[4]helicene moiety.Consequently,a total of four stable products were observed.The atomic topographies of products are characterized by bond-resolving scanning tunneling microscopy.The chiral helicity of targeted products can be switched by tip manipulation.Density-functional-theory calculations unveils the reaction pathway of four products.The com-parative analysis of their respective energy barriers exhibits a correlation with the experimentally determined yields.Furthermore,we synthesize the polymer chains incorporating non-benzenoid carbohelicenes via the Ullmann reaction of 2,6-dibromo-9,10-di(1-naph-thyl)anthracene precursors.Our work proposes a synthetic methodology for several novel helicene-like structures fused with fluorene units and the polymer bearing helicene subunits,thus highlighting the immense potential of these compounds in the application fields of luminescent electronic devices.

HeliceneScanning tunneling microscopyOn-surface synthesisHelicity switchingHydrocarbonsMolecular recognitionNanostructures

Wei Xiong、Xi Geng、Jianchen Lu、Gefei Niu、Boyu Fu、Yi Zhang、Shicheng Li、Yuhang Yang、Nianqiang Li、Lei Gao、Jinming Cai

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Faculty of Materials Science and Engineering,Kunming University of Science and Technology,Kunming,Yunnan 650093,China

Faculty of Science,Kunming University of Science and Technology,Kunming,Yunnan 650093,China

Southwest United Graduate School,Kunming,Yunnan 650093,China

2024

10.1002/cjoc.202400341

中国化学(英文版)
中国化学会 上海有机化学研究所

中国化学(英文版)

CSTPCD
影响因子：0.848
ISSN：1001-604X
年,卷(期)：2024.42(22)