Synthesis, Inhaltsverzeichnis Synthesis 2021; 53(02): 344-347DOI: 10.1055/s-0040-1705950 special topic Functional Organic Molecules One-Pot Synthesis of a Cyclic Pyrene Octamer from Two Bifunctionalized Pyrene Monomers Autoren Peifeng Mei Ryo Kurosaki Akinobu Matsumoto Hiroko Yamada ∗ Naoki Aratani ∗ Artikel empfehlen Abstract Artikel einzeln kaufen(opens in new window) Alle Artikel dieser Rubrik(opens in new window) Abstract A 2,2′-tert-butyl-5,9-6′,8′-cyclooctameric pyrenylene ([8]CP) was synthesized by a one-pot Suzuki–Miyaura cross-coupling reaction from two kinds of bifunctionalized monomers, as a rare example of a cyclic octamer. The octameric molecular structure of [8]CP was revealed by single-crystal X-ray diffraction analysis. Key words Key wordsmacrocycles - pyrene - cross-coupling - X-ray crystal structure - octamer Volltext Referenzen References 1 Toyota S, Tsurumaki E. Chem. Eur. J. 2019; 25: 6878 2 Winkler HJ. S, Wittig G. J. Org. Chem. 1963; 28: 1733 3a Staab HA, Binnig F. Tetrahedron Lett. 1964; 5: 319 3b Xue JY, Ikemoto K, Takahashi N, Izumi T, Taka H, Kita H, Sato S, Isobe H. J. Org. Chem. 2014; 79: 9735 3c Xue JY, Izumi T, Yoshii A, Ikemoto K, Koretsune T, Akashi R, Arita R, Taka H, Kita H, Sato S, Isobe H. Chem. Sci. 2016; 7: 896 4a Jasti R, Bhattacharjee J, Neaton JB, Bertozzi CR. J. Am. Chem. Soc. 2008; 130: 17646 4b Takaba H, Omachi H, Yamamoto Y, Bouffard J, Itami K. Angew. Chem. Int. Ed. 2009; 48: 6112 4c Yamago S, Watanabe Y, Iwamoto T. Angew. Chem. Int. Ed. 2010; 49: 757 5a Zhang J, Wang X, Su Q, Zhi L, Thomas A, Feng X, Su DS, Schlögl R, Müllen K. J. Am. Chem. Soc. 2009; 131: 11296 5b Kurosaki R, Hayashi H, Suzuki M, Jiang J, Hatanaka M, Aratani N, Yamada H. Chem. Sci. 2019; 10: 6785 6a Mei P, Matsumoto A, Hayashi H, Suzuki M, Aratani N, Yamada H. RSC Adv. 2018; 8: 20872 6b Jiang H.-W, Ham S, Aratani N, Kim D, Osuka A. Chem. Eur. J. 2013; 19: 13328 6c Yamamoto Y, Tsurumaki E, Wakamatsu K, Toyota S. Angew. Chem. Int. Ed. 2018; 57: 8199 6d Nakanishi W, Yoshioka T, Taka H, Xue JY, Kita H, Isobe H. Angew. Chem. Int. Ed. 2011; 50: 5323 7 Figueira-Duarte TM, Müllen K. Chem. Rev. 2011; 111: 7260 8 Lorbach D, Keerthi A, Figueira-Duarte TM, Baumgarten M, Wagner M, Müllen K. Angew. Chem. Int. Ed. 2016; 55: 418 9 Ikemoto K, Sato S, Isobe H. Chem. Lett. 2016; 45: 217 10 Venkataramana G, Dongare P, Dawe LN, Thompson DW, Zhao Y, Bodwell GJ. Org. Lett. 2011; 13: 2240 11 Iwamoto T, Kayahara E, Yasuda N, Suzuki T, Yamago S. Angew. Chem. Int. Ed. 2014; 53: 6430 12 Majewski MA, Stępień M. Angew. Chem. Int. Ed. 2019; 58: 86 13 Kurosaki R, Suzuki M, Hayashi H, Fujiki M, Aratani N, Yamada H. Chem. Commun. 2019; 55: 9618 14 Sugita H, Nojima M, Ohta Y, Yokozawa T. Chem. Commun. 2017; 53: 396 15 Sisto TJ, Golder MR, Hirst ES, Jasti R. J. Am. Chem. Soc. 2011; 133: 15800 16 Yang Y.-D, Gong H.-Y. Chem. Commun. 2019; 55: 3701 17 Zwijnenburg MA, Cheng G, McDonald TO, Jelfs KE, Jiang J.-X, Ren S, Hasell T, Blanc F, Cooper AI, Adams DJ. Macromolecules 2013; 46: 7696 18 Lorbach D, Wagner M, Baumgarten M, Müllen K. Chem. Commun. 2013; 49: 10578 19 Kurosaki R, Matsuo K, Hayashi H, Yamada H, Aratani N. Chem. Lett. 2020; 49: 892 20 For the SQUEEZE–Platon program, see: van der Sluis P, Spek AL. Acta Crystallogr., Sect. A: Found. Adv. 1990; 46: 194 Zusatzmaterial Zusatzmaterial Supporting Information (PDF) (opens in new window)
