On-surface synthesis of planar acenes via regioselective aryl–aryl coupling

作者: Pingwu Du , Junfa Zhu , Lin Feng , Tao Wang , Hongxing Jia

DOI: 10.1039/D0CC01043J

关键词:

摘要: The reaction of 2, 2′-dibromo-biphenyl on a Ag (111) surface leads to the formation of planar acenes with a high-regioselectivity rather than nonplanar saddle-shaped tetraphenylene as the typical product in solution chemistry. The regioselective aryl–aryl coupling reaction is attributed to the hydrogen repulsion between the reactants on the confined two-dimensional surface.

参考文章(38)
Jing-Xing Chen, Jian-Wei Han, Henry NC Wong, None, Synthesis and Chiroptical Properties of Double-Helical (M)- and (P)-o-Oligophenylenes. Organic Letters. ,vol. 17, pp. 4296- 4299 ,(2015) , 10.1021/ACS.ORGLETT.5B02102
Carlos-Andres Palma, Manohar Awasthi, Yenny Hernandez, Xinliang Feng, Klaus Müllen, Thomas A. Niehaus, Johannes V. Barth, Sub-Nanometer Width Armchair Graphene Nanoribbon Energy Gap Atlas Journal of Physical Chemistry Letters. ,vol. 6, pp. 3228- 3235 ,(2015) , 10.1021/ACS.JPCLETT.5B01154
Chun-Lin Deng, Xiao-Dong Xiong, David T. W. Chik, Zongwei Cai, Xiao-Shui Peng, Henry N. C. Wong, 6,7-Bismethoxy-2,11-dihydroxytetraphenylene Derived Macrocycles: Synthesis, Structures, and Complexation with Fullerenes Chemistry - An Asian Journal. ,vol. 10, pp. 2342- 2346 ,(2015) , 10.1002/ASIA.201500689
Xinliang Feng, Valentina Marcon, Wojciech Pisula, Michael Ryan Hansen, James Kirkpatrick, Ferdinand Grozema, Denis Andrienko, Kurt Kremer, Klaus Müllen, Towards high charge-carrier mobilities by rational design of the shape and periphery of discotics Nature Materials. ,vol. 8, pp. 421- 426 ,(2009) , 10.1038/NMAT2427
Qitang Fan, Cici Wang, Yong Han, Junfa Zhu, Julian Kuttner, Gerhard Hilt, J. Michael Gottfried, Surface-Assisted Formation, Assembly, and Dynamics of Planar Organometallic Macrocycles and Zigzag Shaped Polymer Chains with C–Cu–C Bonds ACS Nano. ,vol. 8, pp. 709- 718 ,(2014) , 10.1021/NN405370S
Markus Müller, Christian Kübel, Klaus Müllen, Giant Polycyclic Aromatic Hydrocarbons Chemistry: A European Journal. ,vol. 4, pp. 2099- 2109 ,(1998) , 10.1002/(SICI)1521-3765(19981102)4:11<2099::AID-CHEM2099>3.0.CO;2-T
Qiang Sun, Chi Zhang, Huihui Kong, Qinggang Tan, Wei Xu, On-surface aryl-aryl coupling via selective C-H activation. Chemical Communications. ,vol. 50, pp. 11825- 11828 ,(2014) , 10.1039/C4CC05482B
Xinliang Feng, Wojciech Pisula, Klaus Müllen, Large polycyclic aromatic hydrocarbons: Synthesis and discotic organization Pure and Applied Chemistry. ,vol. 81, pp. 2203- 2224 ,(2009) , 10.1351/PAC-CON-09-07-07
Chi Zhang, Qiang Sun, Hua Chen, Qinggang Tan, Wei Xu, Formation of polyphenyl chains through hierarchical reactions: Ullmann coupling followed by cross-dehydrogenative coupling Chemical Communications. ,vol. 51, pp. 495- 498 ,(2015) , 10.1039/C4CC07953A