题目: | On-Surface Debromination of 2,3-Bis(dibromomethyl)- and 2,3-Bis(bromomethyl)naphthalene: Dimerization or Polymerization? |
作者: | Yanning Tang1,+ , Barbara Ejlli2,3,+ , Kaifeng Niu1,+ , Xuechao Li1,+ , Zhengming Hao1, Chaojie Xu1, Haiming Zhang1, Frank Rominger3, Jan Freudenberg3, Uwe H. F. Bunz3, Klaus Muellen2, Lifeng Chi1,4,* |
单位: | 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 |
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. | |
影响因子: | 15.336 |
分区情况: | 一区 |
链接: | https://onlinelibrary.wiley.com/doi/epdf/10.1002/anie.202204123 |
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