Competing pathways to aromaticity governed by amine dehydrogenation and metal-organic complexation in on-surface synthesis.

IF 7.6 1区 化学 Q1 CHEMISTRY, MULTIDISCIPLINARY
Andrés Lombana, Songpol Chaunchaiyakul, Olivier Chuzel, Denis Hagebaum-Reignier, Jean-Luc Parrain, Franck Bocquet, Laurent Nony, Christian Loppacher, Federica Bondino, Elena Magnano, Hiroshi Imada, Emiko Kazuma, Yousoo Kim, Luca Giovanelli, Sylvain Clair
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引用次数: 0

Abstract

We investigated the reactivity of a gem-dichlorovinyl-carbazole precursor in the on-surface synthesis approach. Our findings reveal that, on the Au(111) surface, the thermally-induced dehalogenation reaction led to the formation of cumulene dimers. Contrastingly, the more reactive Cu(111) surface promoted the formation of a polyheterocyclic compound exhibiting extended aromaticity. The latter was found to be related to the dehydrogenation of the amine groups, which did not occur on Au(111), thus promoting the different reactivity observed. At higher annealing temperature, selective C-H activation led to the formation of well-defined organometallic chains. In addition, we found that the amine complexation with metal adatom on Cu(111) was an inhibiting factor for the dimerization reaction, a challenge that could be overcome through proper control of the deposition conditions.

在表面合成中由胺脱氢和金属-有机络合控制的芳香性竞争途径。
我们研究了宝石-二氯酰咔唑前体在表面合成中的反应性。我们的研究结果表明,在Au(111)表面,热诱导的脱卤反应导致了累积烯二聚体的形成。相反,Cu(111)表面的反应性更强,促进了多杂环化合物的形成,具有扩展的芳香性。后者被发现与胺基脱氢有关,而Au(111)上没有发生这种情况,从而促进了观察到的不同反应活性。在较高的退火温度下,选择性C-H活化导致形成定义良好的有机金属链。此外,我们发现铜(111)上的胺与金属原子的络合是二聚化反应的抑制因素,这一挑战可以通过适当控制沉积条件来克服。
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来源期刊
Chemical Science
Chemical Science CHEMISTRY, MULTIDISCIPLINARY-
CiteScore
14.40
自引率
4.80%
发文量
1352
审稿时长
2.1 months
期刊介绍: Chemical Science is a journal that encompasses various disciplines within the chemical sciences. Its scope includes publishing ground-breaking research with significant implications for its respective field, as well as appealing to a wider audience in related areas. To be considered for publication, articles must showcase innovative and original advances in their field of study and be presented in a manner that is understandable to scientists from diverse backgrounds. However, the journal generally does not publish highly specialized research.
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