Synthesis of Azepine- or Azocine-Embedded Hexabenzocoronene-Based Nanographenes

Abstract

Classical polycyclic aromatic hydrocarbons (PAHs) are a large group of π-conjugated planar structures. To explore more properties of PAHs, new structures have been designed, including some with nonplanar topologies and heteroatom-containing moieties. As important nanographene (NG) units, hexabenzocoronene (HBC) and its derivatives have been intensively researched. Many HBC-based nonplanar NGs have been developed, and heteroatom-doped HBC-based NGs have also been designed and synthesized. Here, we summarize some methods for the synthesis of HBC-based NGs containing a seven- or eight-membered ring, and we discuss our newly synthesized NGs containing embedded azepine or azocine moieties, obtained by a modified synthetic route and a conventional Müllen’s synthetic method, respectively.

Key words

nanographenes - Diels–Alder reaction - polycyclic aromatic hydrocarbons - hexabenzocoronenes - azepines - azocines

Publication History

Received: 08 November 2021

Accepted after revision: 22 November 2021

Accepted Manuscript online:
22 November 2021

Article published online:
20 December 2021

• References

• 1a Wang C, Dong H, Hu W, Liu Y, Zhu D. Chem. Rev. 2012; 112: 2208
• 1b Zhang L, Cao Y, Colella NS, Liang Y, Brédas J.-L, Houk KN, Briseno AL. Acc. Chem. Res. 2015; 48: 500
• 2a Pisula W, Feng X, Müllen K. Chem. Mater. 2011; 23: 554
• 2b Wu J, Pisula W, Müllen K. Chem. Rev. 2007; 107: 718
• 3 Lin H.-A, Sato Y, Segawa Y, Nishihara T, Sugimoto N, Scott LT, Higashiyama T, Itami K. Angew. Chem. Int. Ed. 2018; 57: 2874
• 4a Márquez IR, Castro-Fernández S, Millán A, Campaña AG. Chem. Commun. 2018; 54: 6705
• 4b Chaolumen IA. S, Yamada KE, Ito H, Itami K. Angew. Chem. Int. Ed. 2021; 60: 23508
• 4c Qiu Z, Asako S, Hu Y, Ju C.-W, Liu T, Rondin L, Schollmeyer D, Lauret J.-S, Müllen K, Narita A. J. Am. Chem. Soc. 2020; 142: 14814
• 4d Fu X, Han H, Zhang D, Yu H, He Q, Zhao D. Chem. Sci. 2020; 11: 5565
• 4e Pun SH, Wang Y, Chu M, Chan CK, Li Y, Liu Z, Miao Q. J. Am. Chem. Soc. 2019; 141: 9680
• 4f Zou Y, Han Y, Wu S, Hou X, Chow CH. E, Wu J. Angew. Chem. Int. Ed. 2021; 60: 17654
• 5a Wang X.-Y, Yao X, Narita A, Müllen K. Acc. Chem. Res. 2019; 52: 2491
• 5b Hirai M, Tanaka N, Sakai M, Yamaguchi S. Chem. Rev. 2019; 119: 8291
• 5c Stępień M, Gońka E, Żyła M, Sprutta N. Chem. Rev. 2017; 117: 3479
• 5d Kawasumi K, Zhang Q, Segawa Y, Scott LT, Itami K. Nat. Chem. 2013; 5: 739
• 6a Jin E, Yang Q, Ju C.-W, Chen Q, Landfester K, Bonn M, Müllen K, Liu X, Narita A. J. Am. Chem. Soc. 2021; 143: 10403
• 6b Krzeszewski M, Dobrzycki Ł, Sobolewski AL, Cyrański MK, Gryko DT. Angew. Chem. Int. Ed. 2021; 60: 14998
• 6c He B, Dai J, Zherebetskyy D, Chen TL, Zhang BA, Teat ST, Zhang Q, Wang L, Liu Y. Chem. Sci. 2015; 6: 3180
• 6d Bunz UH. F. Acc. Chem. Res. 2015; 48: 1676
• 7a Han Y, Xue Z, Li G, Gu Y, Ni Y, Dong S, Chi C. Angew. Chem. Int. Ed. 2020; 59: 9026
• 7b An P, Chow H.-F, Dietmar K. Synlett 2016; 27: 1255
• 8a Luo J, Xu X, Mao R, Miao Q. J. Am. Chem. Soc. 2012; 134: 13796
• 8b David AH. G, Míguez-Lago S, Cruz CM, Cuerva JM, Blanco V, Campaña AG. Org. Mater. 2021; 3: 51
• 9 Kirschbaum T, Rominger F, Mastalerȥ M. Angew. Chem. Int. Ed. 2020; 59: 270
• 10 Stuparu MC. Acc. Chem. Res. 2021; 54: 2858
• 11 Medel MA, Tapia R, Blanco V, Miguel D, Morcillo SP. Campaña A. G. 2021; 60: 6094
• 12a Yokoi H, Hiraoka Y, Hiroto S, Sakamaki D, Seki S, Shinokubo H. Nat. Commun. 2015; 6: 8215
• 12b Ito S, Tokimaru Y, Nozaki K. Angew. Chem. Int. Ed. 2015; 54: 7256
• 12c Wang X.-Y, Richter M, He Y, Björk J, Riss A, Rajesh R, Garnica M, Hennersdorf F, Weigand JJ, Narita A, Berger R, Feng X, Auwärter W, Barth JV, Palma C.-A, Müllen K. Nat. Commun. 2017; 8: 1948
• 13 An P, Li R, Ma B, He R.-Y, Zhang Y, Xiao M, Zhang B. Angew. Chem. Int. Ed. 2021; 60: 24478
• 14 Marquez IR, Fuentes N, Cruz CM, Puente-Muñoz V, Sotorrios L, Marcos ML, Choquesillo-Lazarte D, Biel B, Crovetto L, Gómez-Bengoa E, González MT, Martin R, Cuerva JM, Campaña AG. Chem. Sci. 2017; 8: 1068
• 15 Grimme S, Antony J, Ehrlich S, Krieg H. J. Chem. Phys. 2010; 132: 154104
• 16 Krishnan R, Binkley JS, Seeger R, Pople JA. J. Chem. Phys. 1980; 72: 650
• 17 Pun SH, Miao Q. Acc. Chem. Res. 2018; 51: 1630
• 18a Geuenich D, Hess K, Köhler F, Herges R. Chem. Rev. 2005; 105: 3758
• 18b Klod S, Kleinpeter E. J. Chem. Soc., Perkin Trans. 2 2001; 1893
• 18c Lu T, Chen F. J. Comput. Chem. 2012; 33: 580