Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 61, Issue 30, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202204123
Keywords
Conjugated Polymers; Dehalogenative Homocoupling; On-Surface Synthesis; Scanning Probe Microscopy
Categories
Funding
- National Natural Science Foundation of China [21790053, 51821002]
- National Major State Basic Research Development Program of China [2017YFA0205000, 2017YFA0205002]
- Collaborative Innovation Center of Suzhou Nano Science Technology
- Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD)
- 111 Project
- Projekt DEAL
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This study reveals the mechanism of on-surface dehalogenative homocoupling of benzylic bromides on Au(111), leading to hydrocarbon dimers or conjugated polymers. Insights into the reaction mechanism were obtained through a combination of experiments and computational calculations.
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.
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