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

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‐bromomethyl naphthalene furnishes a poly (o‐naphthylene vinylidene) as a non‐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.

Object Details

• Location: Deutsche Nationalbibliothek Frankfurt am Main
• Extent: Online-Ressource
• Language: Englisch

References and Relationships

• Bibliographic citation: On‐Surface Debromination of 2,3‐Bis (dibromomethyl)‐ and 2,3‐Bis (bromomethyl) naphthalene: Dimerization or Polymerization? ; day:08 ; month:06 ; year:2022 ; extent:1 ; Angewandte Chemie ; (08.06.2022) (gesamt 1)

Contributors, Places and Time

• Creator: Tang, Yanning ; Ejlli, Barbara ; Niu, Kaifeng ; Li, Xuechao ; Hao, Zhengming ; Xu, Chaojie ; Zhang, Haiming ; Rominger, Frank ; Freudenberg, Jan ; Bunz, Uwe H. F. ; Muellen, Klaus ; Chi, Lifeng

Further information

• DOI: 10.1002/ange.202204123
• URN: urn:nbn:de:101:1-2022060815170210547673
• Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
• Last update: 15.08.2025, 7:36 AM CEST