On-Surface Debromination of 2,3-Bis(dibromomethyl)- and 2,3-Bis(bromomethyl)naphthalene: Dimerization or Polymerization? was written by 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. And the article was included in Angewandte Chemie, International Edition in 2022.Electric Literature of C4H4BrNO2 This article mentions the following:
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 at. force microscopy and d. functional theory calculations provides deep insights into the prevailing mechanisms. In the experiment, the researchers used many compounds, for example, 1-Bromopyrrolidine-2,5-dione (cas: 128-08-5Electric Literature of C4H4BrNO2).
1-Bromopyrrolidine-2,5-dione (cas: 128-08-5) belongs to organobromine compounds. Bromine is more electronegative than carbon (2.9 vs 2.5). Consequently, the carbon in a carbon–bromine bond is electrophilic, i.e. alkyl bromides are alkylating agents. The principal reactions for organobromides include dehydrobromination, Grignard reactions, reductive coupling, and nucleophilic substitution.Electric Literature of C4H4BrNO2
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary