Exploiting Cooperative Catalysis for the On-Surface Synthesis of Linear Heteroaromatic Polymers via Selective C-H Activation

. 2022 Jan 26 ; 61 (5) : e202112798. [epub] 20211214

Status PubMed-not-MEDLINE Jazyk angličtina Země Německo Médium print-electronic

Typ dokumentu časopisecké články

Perzistentní odkaz   https://www.medvik.cz/link/pmid34788494

Grantová podpora
RE2669/7 Deutsche Forschungsgemeinschaft
PA3628/1 Deutsche Forschungsgemeinschaft
GACR 20-13692X Akademie Věd České Republiky
PP00P2_157615, PP00P2_187185 Schweizerischer Nationalfonds zur Förderung der Wissenschaftlichen Forschung
200021_204053 Schweizerischer Nationalfonds zur Förderung der Wissenschaftlichen Forschung
LM2018110 CzechNanoLab Research Infrastructure
LM2015085 Grantová Agentura České Republiky

Regiospecific C-H activation is a promising approach to achieve extended polymers with tailored structures. While a recent on-surface synthetic approach has enabled regioselective homocoupling of heteroaromatic molecules, only small oligomers have been achieved. Herein, selective C-H activation for dehydrogenative C-C couplings of hexaazatriphenylene by Scholl reaction is reported for the first time. By combining low-temperature scanning tunneling microscopy (STM) and atomic force microscopy (AFM), we revealed the formation of one-dimensional polymers with a double-chain structure. The details of the growth process are rationalized by density functional theory (DFT) calculations, pointing out a cooperative catalytic action of Na and Ag adatoms in steering the C-H selectivity for the polymerization.

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Grzybowski M., Skonieczny K., Butenschoen H., Gryko D. T., Angew. Chem. Int. Ed. 2013, 52, 9900–9930; PubMed

Angew. Chem. 2013, 125, 10084–10115.

Sarhan A. A., Bolm C., Chem. Soc. Rev. 2009, 38, 2730–2744. PubMed

Myśliwiec D., Donnio B., Chmielewski P. J., Heinrich B., Stępień M., J. Am. Chem. Soc. 2012, 134, 4822–4833. PubMed

Cao Y., Wang X.-Y., Wang J.-Y., Pei J., Synlett 2014, 25, 313–323.

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

Little M. S., Yeates S. G., Alwattar A. A., Heard K. W., Raftery J., Edwards A. C., Parry A. V., Quayle P., Eur. J. Org. Chem. 2017, 1694–1703.

Han Y., Xue Z., Li G., Gu Y., Ni Y., Dong S., Chi C., Angew. Chem. Int. Ed. 2020, 59, 9026–9031; PubMed

Angew. Chem. 2020, 132, 9111–9116.

Uryu M., Hiraga T., Koga Y., Saito Y., Murakami K., Itami K., Angew. Chem. Int. Ed. 2020, 59, 6551–6554; PubMed

Angew. Chem. 2020, 132, 6613–6616.

Ito H., Segawa Y., Murakami K., Itami K., J. Am. Chem. Soc. 2019, 141, 3–10. PubMed

King B. T., Kroulík J., Robertson C. R., Rempala P., Hilton C. L., Korinek J. D., Gortari L. M., J. Org. Chem. 2007, 72, 2279–2288. 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

Grill L., Hecht S., Nat. Chem. 2020, 12, 115–130. PubMed

Ruffieux P., Wang S., Yang B., Sánchez-Sánchez C., Liu J., Dienel T., Talirz L., Shinde P., Pignedoli C. A., Passerone D., Dumslaff T., Feng X., Müllen K., Fasel R., Nature 2016, 531, 489–492. PubMed

Liu J., Berger R., Müllen K., Feng X., From Polyphenylenes to Nanographenes and Graphene Nanoribbons, Springer, Heidelberg, 2017, pp. 1–32.

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

Clair S., de Oteyza D. G., Chem. Rev. 2019, 119, 4717–4776. PubMed PMC

Fan Q., Werner S., Tschakert J., Ebeling D., Schirmeisen A., Hilt G., Hieringer W., Gottfried J. M., J. Am. Chem. Soc. 2018, 140, 7526–7532. PubMed

Sun Q., Zhang C., Kong H., Tan Q., Xu W., Chem. Commun. 2014, 50, 11825–11828. PubMed

Wang C.-X., Jin Q., Shu C.-H., Hua X., Long Y.-T., Liu P.-N., Chem. Commun. 2017, 53, 6347–6350. PubMed

Kocić N., Liu X., Chen S., Decurtins S., Krejčí O., Jelínek P., Repp J., Liu S. X., J. Am. Chem. Soc. 2016, 138, 5585–5593. PubMed

Sonogashira K., Tohda Y., Hagihara N., Tetrahedron Lett. 1975, 16, 4467–4470.

Bi Q., Huang X., Yin G., Chen T., Du X., Cai J., Xu J., Liu Z., Han Y., Huang F., ChemCatChem 2019, 11, 1295–1302.

Sammis G. M., Danjo H., Jacobsen E. N., J. Am. Chem. Soc. 2004, 126, 9928–9929. PubMed

Patera L. L., Liu X., Mosso N., Decurtins S., Liu S.-X., Repp J., Angew. Chem. Int. Ed. 2017, 56, 10786–10790; PubMed

Angew. Chem. 2017, 129, 10926–10930.

Freund S., Pawlak R., Moser L., Hinaut A., Steiner R., Marinakis N., Constable E. C., Meyer E., Housecroft C. E., Glatzel T., ACS Omega 2018, 3, 12851–12856. PubMed PMC

Meier T., Pawlak R., Kawai S., Geng Y., Liu X., Decurtins S., Hapala P., Baratoff A., Liu S.-X., Jelínek P., Meyer E., Glatzel T., ACS Nano 2017, 11, 8413–8420. PubMed

Bowker M., Waugh K., Surf. Sci. 1983, 134, 639–664.

Wäckerlin C., Iacovita C., Chylarecka D., Fesser P., Jung T. A., Ballav N., Chem. Commun. 2011, 47, 9146. PubMed

Shimizu T. K., Jung J., Imada H., Kim Y., Angew. Chem. Int. Ed. 2014, 53, 13729–13733; PubMed

Angew. Chem. 2014, 126, 13949–13953.

Zhou K., Liang H., Wang M., Xing S., Ding H., Song Y., Wang Y., Xu Q., He J.-H., Zhu J., Zhao W., Ma Y., Shi Z., Nanoscale Adv. 2020, 2, 2170–2176. PubMed PMC

Hieulle J., Peyrot D., Jiang Z., Silly F., Chem. Commun. 2015, 51, 13162–13165. PubMed

Zhang C., Wang L., Xie L., Kong H., Tan Q., Cai L., Sun Q., Xu W., ChemPhysChem 2015, 16, 2099–2105. PubMed

Zhang C., Xie L., Wang L., Kong H., Tan Q., Xu W., J. Am. Chem. Soc. 2015, 137, 11795–11800. PubMed

Skomski D., Abb S., Tait S. L., J. Am. Chem. Soc. 2012, 134, 14165–14171. PubMed

Gross L., Mohn F., Moll N., Liljeroth P., Meyer G., Science 2009, 325, 1110–1114. PubMed

Queck F., Krejčí O., Scheuerer P., Bolland F., Otyepka M., Jelínek P., Repp J., J. Am. Chem. Soc. 2018, 140, 12884–12889. PubMed

Patera L. L., Zou Z., Dri C., Africh C., Repp J., Comelli G., Phys. Chem. Chem. Phys. 2017, 19, 24605–24612. PubMed

Yang Z., Gebhardt J., Schaub T. A., Sander T., Schönamsgruber J., Soni H., Görling A., Kivala M., Maier S., Nanoscale 2018, 10, 3769–3776. PubMed

Hapala P., Kichin G., Wagner C., Tautz F. S., Temirov R., Jelínek P., Phys. Rev. B 2014, 90, 085421. PubMed

Kong H., Zhang C., Sun Q., Yu X., Xie L., Wang L., Li L., Hu S., Ju H., He Y., Zhu J., Xu W., ACS Nano 2018, 12, 9033–9039. PubMed

Fritton M., Duncan D. A., Deimel P. S., Rastgoo-Lahrood A., Allegretti F., Barth J. V., Heckl W. M., Björk J., Lackinger M., J. Am. Chem. Soc. 2019, 141, 4824–4832. PubMed

Patera L. L., Bianchini F., Africh C., Dri C., Soldano G., Mariscal M. M., Peressi M., Comelli G., Science 2018, 359, 1243–1246. PubMed

de la Torre B., Matěj A., Sánchez-Grande A., Cirera B., Mallada B., Rodríguez-Sánchez E., Santos J., Mendieta-Moreno J. I., Edalatmanesh S., Lauwaet K., Otyepka M., Medveď M., Buendía Á., Miranda R., Martín N., Jelínek P., Écija D., Nat. Commun. 2020, 11, 4567. PubMed PMC

Mendieta-Moreno J. I., Walker R. C., Lewis J. P., Gómez-Puertas P., Mendieta J., Ortega J., J. Chem. Theory Comput. 2014, 10, 2185–2193. PubMed

Kumar S., Rosenberg J. M., Bouzida D., Swendsen R. H., Kollman P. A., J. Comput. Chem. 1992, 13, 1011–1021.

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