Direct transformation of n-alkane into all- trans conjugated polyene via cascade dehydrogenation

Xuechao Li; Kaifeng Niu; Junjie Zhang; Xiaojuan Yu; Haiming Zhang; Yuemin Wang; Qing Guo; Pengdong Wang; Fangsen Li; Zhengming Hao; Chaojie Xu; Yanning Tang; Zhichao Xu; Shuai Lu; Peng Liu; Guigu Xue; Yen Wei; Lifeng Chi

doi:10.1093/nsr/nwab093

Direct transformation of n-alkane into all- trans conjugated polyene via cascade dehydrogenation

Natl Sci Rev. 2021 May 24;8(10):nwab093. doi: 10.1093/nsr/nwab093. eCollection 2021 Oct.

Authors

Xuechao Li¹, Kaifeng Niu¹, Junjie Zhang¹, Xiaojuan Yu², Haiming Zhang¹, Yuemin Wang², Qing Guo³, Pengdong Wang⁴, Fangsen Li⁴, Zhengming Hao¹, Chaojie Xu¹, Yanning Tang¹, Zhichao Xu¹, Shuai Lu¹, Peng Liu³, Guigu Xue³, Yen Wei⁵, Lifeng Chi¹

Affiliations

¹ Jiangsu Key Laboratory for Carbon Based Functional Materials & Devices, Institute of Functional Nano & Soft Materials, Soochow University, Suzhou 215123, China.
² Institute of Functional Interfaces, Karlsruhe Institute of Technology, Eggenstein-Leopoldshafen 76344, Germany.
³ Department of Chemistry, Southern University of Science and Technology, Shenzhen 518055, China.
⁴ Vacuum Interconnected Nanotech Workstation (Nano-X), Suzhou Institute of Nano-Tech and Nano-Bionics, Chinese Academy of Sciences, Suzhou 215123, China.
⁵ Key Laboratory of Organic Optoelectronics and Molecular Engineering, Department of Chemistry, Tsinghua University, Beijing 100084, China.

Abstract

Selective C(sp³) -H activation is of fundamental importance in processing alkane feedstocks to produce high-value-added chemical products. By virtue of an on-surface synthesis strategy, we report selective cascade dehydrogenation of n-alkane molecules under surface constraints, which yields monodispersed all-trans conjugated polyenes with unprecedented length controllability. We are also able to demonstrate the generality of this concept for alkyl-substituted molecules with programmable lengths and diverse functionalities, and more importantly its promising potential in molecular wiring.

Keywords: C(sp3)–H activation; alkane transformation; dehydrogenation; molecular wiring; on-surface synthesis.