2016
DOI: 10.1039/c6cc03137d
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Ullmann coupling reaction of aryl chlorides on Au(111) using dosed Cu as a catalyst and the programmed growth of 2D covalent organic frameworks

Abstract: The efficiency of Ullmann reaction of aryl chlorides on an Au(111) surface has been substantially increased by using dosed Cu as a catalyst. The different reactivity of aryl bromides and aryl chlorides has been exploited to design a programmed, on-surface synthesis to form 2D covalent organic frameworks.

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Cited by 47 publications
(40 citation statements)
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“…Solid-vapor interface synthesis is often used by combination with ultrahigh vacuum (UHV) method [ 107 , 136 , 137 , 138 , 139 , 140 , 180 , 181 ]. Halogenate monomers will be turned into vapor at first and deposited on the surface of clean metal surface under ultrahigh vacuum.…”
Section: Developments Of Cofsmentioning
confidence: 99%
“…Solid-vapor interface synthesis is often used by combination with ultrahigh vacuum (UHV) method [ 107 , 136 , 137 , 138 , 139 , 140 , 180 , 181 ]. Halogenate monomers will be turned into vapor at first and deposited on the surface of clean metal surface under ultrahigh vacuum.…”
Section: Developments Of Cofsmentioning
confidence: 99%
“…46 The result was rationalized by the fact that the C–Cl bond is stronger than the C–Br bond. 4749 As a consequence, for DCBA, the dehalogenation temperature is elevated relative to that for DBBA and is higher than the cyclodehydrogenation temperature. This leads to a reversed reaction sequence, with cyclodehydrogenation preceding covalent coupling.…”
Section: Introductionmentioning
confidence: 99%
“…The exact sequence of thermally induced transformations is an interplay between the precursor molecule of interest and the metal substrate, and can additionally be affected by coadsorbed species. 4951 Understanding what product is obtained therefore requires an understanding of the various elementary reaction steps and their activation temperatures. Although scanning tunneling microscopy (STM) and noncontact atomic force microscopy (nc-AFM) imaging allow the identification of reaction products and intermediates, these techniques lack the ability to monitor chemical transformations at annealing temperatures.…”
Section: Introductionmentioning
confidence: 99%
“…A large variety of surface‐supported 2D networks were fabricated in ultrahigh vacuum (UHV) environment or at the liquid‐solid interface . In the latter case thermodynamic equilibrium conditions can be reached and extended well‐ordered networks can be formed.…”
Section: Figurementioning
confidence: 99%
“…Further annealing up to 510 °C allowed to improve the network quality and the PH score raised to 0.30 (Figure c). The same honeycomb network could be obtained using a sequential coupling strategy with a precursor bearing two different halogen types (4,4′′‐dichloro‐1,1′ : 4′,1′′‐terphenyl, DCTP, Figure d) . The low quality network obtained on Au(111) with the help of codeposited Cu adatom catalysts delivered a PH score of 0.16 (Figure e).…”
Section: Figurementioning
confidence: 99%