Flattening helices while keeping the handedness: On-surface cyclodehydrogenation of bishelicene enantiomers leads stereospecifically to (M,M) and (P,P) chiral planar polyaromatic hydrocarbons. This is followed by their homochiral aggregation into a 2D conglomerate. Thermally induced cyclodehydrogenation proceeds stereospecifically to chiral, planar coronocoronene. Such a reaction is a special example of topochemistry in which enantiospecific conversion is supported by the alignment of the reactant by the surface.

Department of Chemistry University of Zurich Winterthurerstrasse 190 8057 Zürich Switzerland

Molecular Surface Science and Coating Technology Laboratory Empa Swiss Federal Laboratories for Materials Science and Technology Überlandstrasse 129 8600 Dübendorf Switzerland

MOLTECH Anjou UMR 6200 CNRS UNIV Angers 2 bd Lavoisier 49045 Angers Cedex France

Nanosurf Laboratory Institute of Physics The Czech Academy of Sciences Cukrovarnická 10 162 00 Prague Czech Republic

Zobrazit více v PubMed

Zhi L., Müllen K., J. Mater. Chem. 2008, 18, 1472–1484.

Müllen K., Rabe J. P., Acc. Chem. Res. 2008, 41, 511–520. PubMed

Narita A., Wang X.-Y., Feng X., Müllen K., Chem. Soc. Rev. 2015, 44, 6616–6643. PubMed

Koga Y., Kaneda T., Saito Y., Murakami K., Itami K., Science 2018, 359, 435–439. PubMed

Fan Q., Gottfried J. M., Zhu J., Acc. Chem. Res. 2015, 48, 2484–2494. PubMed

Dong L., Liu P. N., Lin N., Acc. Chem. Res. 2015, 48, 2765–2774. PubMed

Klappenberger F., Zhang Y.-Q., Björk J, Klyatskaya S., Ruben M., Barth J. V., Acc. Chem. Res. 2015, 48, 2140–2150. PubMed

Cai J., Ruffieux P., Jaafar R., Bieri M., Braun T., Blankenburg S., Muoth M., Seitsonen A. P., Saleh M., Feng X., Müllen K., Fasel R., Nature 2010, 466, 470–473. PubMed

Sanchez-Valencia J. R., Dienel T., Gröning O., Shorubalko I., Mueller A., Jansen M., Amsharov K., Ruffieux P., Fasel R., Nature 2015, 512, 61–64. PubMed

Beernink G., Dötz F., Birkner A., Müllen K., Wöll C., Angew. Chem. Int. Ed. 1999, 38, 3748–3752. PubMed

Beernink G., Gunia M., Dötz F., Ostrom H., Weiss K., Müllen K., Wöll C., ChemPhysChem 2001, 2, 317–320. PubMed

Zuzak R., Castro-Esteban J., Brandimarte P., Engelund M., Cobas A., Piątkowski P., Kolmer M., Pérez D., Guitián E., Szymonski M., Sánchez-Portal D., Godlewski S., Peña D., Chem. Commun. 2018, 54, 10256–10259. PubMed

Chen H., Tao L., Wang D., Wu Z.-Y., Zhang J.-L., Gao S., Xiao W., Du S., Ernst K.-H., Gao H.-J., Angew. Chem. Int. Ed. 2020, 59, 17413–17416. PubMed

Wäckerlin C., Li J., Mairena A., Martin K., Avarvari N., Ernst K.-H., Chem. Commun. 2016, 52, 12694–12697. PubMed

Li J., Martin K., Avarvari N., Wäckerlin C., Ernst K.-H., Chem. Commun. 2018, 54, 7948–7951. PubMed

Mairena A., Baljozović M., Kawecki M., Grenader K., Wienke M., Martin K., Bernard L., Avarvari N., Terfort A., Ernst K.-H., Wäckerlin C., Chem. Sci. 2019, 10, 2998–3004. PubMed PMC

Stetsovych O., Švec M., Vacek J., Chocholoušová J. V., Jancarik A., Rybáček J., Kosmider K., Stará I. G., Jelínek P., Starý I., Nat. Chem. 2017, 9, 213–218; PubMed

Ernst K.-H., Nat. Chem. 2017, 9, 195–196. PubMed

Barth J., Brune H., Ertl G., Behm R., Phys. Rev. B 1990, 42, 9307–9318. PubMed

Björk J., Stafström S., Hanke F., J. Am. Chem. Soc. 2011, 133, 14884–14887. PubMed

Medeiros P. V. C., Gueorguiev G. K., Stafström S., Phys. Rev. B 2012, 85, 205423/1–7.

de Oteyza D. G., Garcia-Lekue A., Vilas-Varela M., Merino-Diez N., Carbonell-Sanroma E., Corso M., Vasseur G., Rogero C., Guitian E., Pascual J. I., Ortega J. E., Wakayama Y., Pena D., ACS Nano 2016, 10, 9000–9008. PubMed PMC

Merino-Díez N., Mohammed M. S. G., Castro-Esteban J., Colazzo L., Berdonces-Layunta A., Lawrence J., Pascual J. I., de Oteyza D. G., Peña D., Chem. Sci. 2020, 11, 5441–5446. PubMed PMC

Keerthi A., Sánchez-Sánchez C., Deniz O., Ruffieux P., Schollmeyer D., Feng X., Narita A., Fasel R., Müllen K., Chem. Asian J. 2020, 15, 3807–3811. PubMed PMC

Blankenburg S., Ruffieux J. P., Jaafar R., Passerone D., Feng X., Müllen K., Fasel R., Pignedoli C. A., ACS Nano 2012, 6, 2020–2025. PubMed

Mairena A., Wäckerlin C., Wienke M., Grenader K., Terfort A., Ernst K.-H. J. Am. Chem. Soc. 2018, 140, 15186–15189. PubMed