- Direct Formation of C?C Triple-Bonded Structural Motifs by On-Surface Dehalogenative Homocouplings of Tribromomethyl-Substituted Arenes
-
On-surface synthesis shows significant potential in constructing novel nanostructures/nanomaterials, which has been intensely studied in recent years. The formation of acetylenic scaffolds provides an important route to the fabrication of emerging carbon nanostructures, including carbyne, graphyne, and graphdiyne, which feature chemically vulnerable sp-hybridized carbon atoms. Herein, we designed and synthesized a tribromomethyl-substituted compound. By using a combination of high-resolution scanning tunneling microscopy, non-contact atomic force microscopy, and density functional theory calculations, we demonstrated that it is feasible to convert these compounds directly into C?C triple-bonded structural motifs by on-surface dehalogenative homocoupling reactions. Concurrently, sp3-hybridized carbon atoms are converted into sp-hybridized ones, that is, an alkyl group is transformed into an alkynyl moiety. Moreover, we achieved the formation of dimer structures, one-dimensional molecular wires, and two-dimensional molecular networks on Au(111) surfaces, which should inspire further studies towards two-dimensional graphyne structures.
- Sun, Qiang,Yu, Xin,Bao, Meiling,Liu, Mengxi,Pan, Jinliang,Zha, Zeqi,Cai, Liangliang,Ma, Honghong,Yuan, Chunxue,Qiu, Xiaohui,Xu, Wei
-
-
Read Online
- Concomitant but disappearing: Two polymorphs of 1,4-bis-(tribromomethyl) benzene
-
The title compound, C8H4Br6, (I), initially crystallized from deuterochloro-form as the comcomitant polymorphs (Ia) (prisms, space group P21/n, Z = 2) and (Ib) (hexa-gonal plates, space group C2/c, Z = 4). The molecules in both forms
- Jones, Peter G.,Hopf, Henning,Silaghi, Anamaria,Naether, Christian
-
-
Read Online
- Photothermal Side-Chain Bromination of Methyl-, Dimethyl-, and Trimethylbenzenes with N-Bromosuccinimide
-
Tri- and dibromination of methyl-, dimethyl-, and trimethylbenzenes with N-bromosuccinimide were accomplished by photothermal reaction with a tungsten lamp in carbon tetrachloride or benzene. (Dibromomethyl)arenes and (tribromomethyl) derivatives were produced depending upon a solvent used and a substituent on the benzene ring.In the bromination of methylbenzenes without a substituent on the ortho-position, (tribromomethyl)benzenes were formed.On the other hand, ortho-substituted methylbenzenes gave (dibromomethyl)benzenes. α,β-Dibromo-1,2-diarylstilbenes were formed via the debrominative carbon-carbon coupling reaction of ...
- Mataka, Shuntaro,Liu, Guo-Bin,Sawada, Tsuyoshi,Kurisu, Masayoshi,Tashiro, Masashi
-
p. 1113 - 1119
(2007/10/02)
-