Angew. Chem. Int. Ed.: On-Surface Debromination of 2,3-Bis(dibromomethyl)- and 2,3-Bis(bromomethyl)naphthalene: Dimerization or Polymerization?

Title ：

On-Surface Debromination of 2,3-Bis(dibromomethyl)- and 2,3-Bis(bromomethyl)naphthalene: Dimerization or Polymerization?

Authors ：

Yanning Tang^1,+ , Barbara Ejlli^2,3,+ , Kaifeng Niu^1,+ , Xuechao Li^1,+ , Zhengming Hao¹, Chaojie Xu¹, Haiming Zhang¹, Frank Rominger³, Jan Freudenberg³, Uwe H. F. Bunz³, Klaus Muellen², Lifeng Chi^1,4,*

Institutions ：

¹Institute of Functional Nano & Soft Materials (FUNSOM), Jiangsu Key Laboratory for Carbon-Based Functional Materials and Devices, Joint International Research Laboratory of Carbon-Based Functional Materials and Devices, Soochow University, Ren’ai road No. 199, Suzhou, Jiangsu 215123, China

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

³Organisch Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 27069120 Heidelberg, German

⁴Macao Institute of Materials Science and Engineering (MIMSE), MUST-SUDA Joint Research Center for Advanced Functional Materials, Macau University of Science and Technology, Taipa 999078, Macao, China

Abstract ：

We describe the on-surface dehalogenative homocoupling of benzylic bromides, namely bis-bromomethyl-and bis-gem-(dibromomethyl)naphthalene as a potential route to either hydrocarbon dimers or conjugated polymers on Au(111). While bis-gem-(dibromomethyl)naphthalene affords different dimers with naphthocyclobutadiene as the key intermediate, bis-bromomethylnaphthalene furnishes a poly(o-naphthylene vinylidene) as anon-conjugated polymer which undergoes dehydrogenation toward its conjugated derivative poly(o-naphthylene vinylene) upon mild annealing. A combination of scanning tunneling microscopy, non-contact atomic force microscopy and density functional theory calculations provides deep insights into the prevailing mechanisms.

IF ：

15.336

https://onlinelibrary.wiley.com/doi/epdf/10.1002/anie.202204123