Control of Reactivity and Regioselectivity for On-Surface Dehydrogenative Aryl–Aryl Bond Formation

作者: Nemanja Kocić , Xunshan Liu , Songjie Chen , Silvio Decurtins , Ondřej Krejčí

DOI: 10.1021/JACS.5B13461

关键词:

摘要: Regioselectivity is of fundamental importance in chemical synthesis. Although many concepts for site-selective reactions are well established solution chemistry, it not a priori clear whether they can easily be transferred to taking place on metal surface. A will fix the potential electrons and perturb electronic states reactants because hybridization. Additionally, techniques characterize generally applicable on-surface reactions. Only recent developments resolving structures by atomic force microscopy (AFM) scanning tunneling (STM) paved way identifying individual reaction products surfaces. Here we exploit combined STM/AFM technique demonstrate formation complex molecular architectures built up from heteroaromatic precursor, tetracyclic pyrazino[2,3-f][4,7]phenanthroline (pap) molecule. Selective intermolecular aryl–aryl coupling via dehy...

参考文章(77)
Hilde Grove, Jorunn Sletten, Crystal structures of 4,7-phenanthrolino-5,6:5′,6′-pyrazine tetrahydrate and 1,4,5,8,9,12-hexaazatriphenylene dihydrate Journal of Chemical Crystallography. ,vol. 30, pp. 123- 130 ,(2000) , 10.1023/A:1009573713893
Shigeki Kawai, Shohei Saito, Shinichiro Osumi, Shigehiro Yamaguchi, Adam S. Foster, Peter Spijker, Ernst Meyer, Atomically controlled substitutional boron-doping of graphene nanoribbons Nature Communications. ,vol. 6, pp. 8098- 8098 ,(2015) , 10.1038/NCOMMS9098
Thomas Dienel, Shigeki Kawai, Hajo Söde, Xinliang Feng, Klaus Müllen, Pascal Ruffieux, Roman Fasel, Oliver Gröning, Resolving Atomic Connectivity in Graphene Nanostructure Junctions. Nano Letters. ,vol. 15, pp. 5185- 5190 ,(2015) , 10.1021/ACS.NANOLETT.5B01403
Iván González, Paulina Dreyse, Diego Cortés-Arriagada, Mahesh Sundararajan, Claudio Morgado, Iván Brito, Cristina Roldán-Carmona, Henk J Bolink, Bárbara Loeb, None, A comparative study of Ir(III) complexes with pyrazino[2,3-f][1,10]phenanthroline and pyrazino[2,3-f][4,7]phenanthroline ligands in light-emitting electrochemical cells (LECs) Dalton Transactions. ,vol. 44, pp. 14771- 14781 ,(2015) , 10.1039/C5DT01385B
Akimitsu Narita, Xiao-Ye Wang, Xinliang Feng, Klaus Müllen, New advances in nanographene chemistry Chemical Society Reviews. ,vol. 44, pp. 6616- 6643 ,(2015) , 10.1039/C5CS00183H
L. Gross, F. Mohn, N. Moll, P. Liljeroth, G. Meyer, The Chemical Structure of a Molecule Resolved by Atomic Force Microscopy Science. ,vol. 325, pp. 1110- 1114 ,(2009) , 10.1126/SCIENCE.1176210
Chandima Abeywickrama, Arthur David Baker, Efficient Synthesis of 1,4,5,12-Tetraazatriphenylene and Derivatives Journal of Organic Chemistry. ,vol. 69, pp. 7741- 7744 ,(2004) , 10.1021/JO0495283
D. G. de Oteyza, P. Gorman, Y.-C. Chen, S. Wickenburg, A. Riss, D. J. Mowbray, G. Etkin, Z. Pedramrazi, H.-Z. Tsai, A. Rubio, M. F. Crommie, F. R. Fischer, Direct Imaging of Covalent Bond Structure in Single-Molecule Chemical Reactions Science. ,vol. 340, pp. 1434- 1437 ,(2013) , 10.1126/SCIENCE.1238187
Christopher D. Simpson, J. Diedrich Brand, Alexander J. Berresheim, Laurence Przybilla, Hans Joachim Räder, Klaus Müllen, Synthesis of a giant 222 carbon graphite sheet. Chemistry: A European Journal. ,vol. 8, pp. 1424- 1429 ,(2002) , 10.1002/1521-3765(20020315)8:6<1424::AID-CHEM1424>3.0.CO;2-Z
Daniel J. Gregg, Eberhard Bothe, Petra Höfer, Paolo Passaniti, Sylvia M. Draper, Extending the nitrogen-heterosuperbenzene family: the spectroscopic, redox, and photophysical properties of "half-cyclized" N-1/2HSB and Its Ru(II) complex. Inorganic Chemistry. ,vol. 44, pp. 5654- 5660 ,(2005) , 10.1021/IC050335N