Zuzak Rafal, Stoica Otilia, Blieck Rémi, Echavarren Antonio M, Godlewski Szymon
Centre for Nanometer-Scale Science and Advanced Materials, NANOSAM, Faculty of Physics, Astronomy and Applied Computer Science, Jagiellonian University, Łojasiewicza 11, PL 30-348 Krakow, Poland.
Institute of Chemical Research of Catalonia (ICIQ), Barcelona Institute of Science and Technology, Avenida Països Catalans 16, 43007 Tarragona, Spain.
ACS Nano. 2021 Jan 26;15(1):1548-1554. doi: 10.1021/acsnano.0c08995. Epub 2020 Dec 21.
The formation of -indaceno[1,2-:5,6-']ditetracene and -indaceno[2,3-:6,7-']ditetracene containing indenofluorene cores from a common precursor has been achieved by a dehydrogenative surface-assisted cyclization on Au(111) and confirmed by bond-resolved non-contact atomic force microscopy. On-surface generated -indaceno[2,3-:6,7-']ditetracenes undergo fusion, which leads to T-shaped adducts by an intermolecular cycloaddition. The same type of cycloaddition, which has no parallel in solution chemistry, has been observed between -indaceno[2,3-:6,7-']ditetracene and pentacene or octacene. These examples of surface-assisted cycloaddition provide perspectives for the rational design and synthesis of molecular nanostructures.
通过在Au(111)上进行脱氢表面辅助环化反应，已从一种常见前体实现了含有茚并芴核的-茚并[1,2-:5,6-']二并四苯和-茚并[2,3-:6,7-']二并四苯的形成，并通过键分辨非接触原子力显微镜得到证实。表面生成的-茚并[2,3-:6,7-']二并四苯会发生融合，通过分子间环加成反应形成T形加合物。在-茚并[2,3-:6,7-']二并四苯与并五苯或并八苯之间也观察到了同样类型的环加成反应，这种反应在溶液化学中并无类似情况。这些表面辅助环加成的例子为分子纳米结构的合理设计与合成提供了思路。
