Bilateral π-extension of an open-[60]fullerene in a helical manner

1 (a) M. Murata, Y. Murata and K. Komatsu, Chem. Commun., 2008,

6083–6094; (b) G. C. Vougioukalakis, M. M. Roubelakis and

M. Orfanopoulos, Chem. Soc. Rev., 2010, 39, 817–844; (c) L. Shi

and L. Gan, J. Phys. Org. Chem., 2013, 26, 766–772.

2 L. T. Scott, E. A. Jackson, Q. Zhang, B. D. Steinberg, M. Bancu and

B. Li, J. Am. Chem. Soc., 2012, 134, 107–110.

3 B. Liu, J. Liu, H.-B. Li, R. Bhola, E. A. Jackson, L. T. Scott, A. Page,

S. Irle, K. Morokuma and C. Zhou, Nano Lett., 2015, 15, 586–595.

4 H. Omachi, T. Nakayama, E. Takahashi, Y. Segawa and K. Itami, Nat.

Chem., 2013, 5, 572–576.

¨ning, I. Shorubalko,

5 (a) J. R. Sanchez-Valencia, T. Dienel, O. Gro

A. Mueller, M. Jansen, K. Amsharov, P. Ruffieux and R. Fasel, Nature,

2014, 512, 61–64; (b) J. Tomada, T. Dienel, F. Hampel, R. Fasel and

K. Amsharov, Nat. Commun., 2019, 10, 3278.

6 X. Yu, J. Zhang, W. Choi, J.-Y. Choi, J. M. Kim, L. Gan and Z. Liu,

Nano Lett., 2010, 10, 3343–3349.

7 L. T. Scott, Pure Appl. Chem., 2017, 89, 809–820.

8 C.-S. Chen and W.-Y. Yeh, Chem. – Eur. J., 2016, 22, 16425–16428.

9 (a) S.-i Iwamatsu, T. Uozaki, K. Kobayashi, S. Re, S. Nagase and

S. Murata, J. Am. Chem. Soc., 2004, 126, 2668–2669; (b) Z. Xiao, G. Ye,

Y. Liu, S. Chen, Q. Peng, Q. Zuo and L. Ding, Angew. Chem., Int. Ed.,

2012, 51, 9038–9041.

10 (a) Y. Hashikawa, S. Sadai and Y. Murata, Org. Lett., 2021, 23,

9586–9590; (b) Y. Hashikawa, N. Fujikawa and Y. Murata, J. Am.

Chem. Soc., 2022, 144, 23292–23296; (c) S. Sadai, Y. Hashikawa and

Y. Murata, Org. Lett., 2023, 25, 2815–2819.

11 (a) Y. Yu, L. Xu, X. Huang and L. Gan, J. Org. Chem., 2014, 79,

2156–2162; (b) Z. Liu, Z. Liu, R. Gao, J. Su, Y. Qiu and L. Gan, Org.

Chem. Front., 2022, 9, 320–328.

12 (a) Y. Hashikawa, H. Yasui, K. Kurotobi and Y. Murata, Mater. Chem.

Front., 2018, 2, 206–213; (b) Y. Hashikawa, S. Okamoto and

Y. Murata, Commun. Chem., 2020, 3, 90; (c) Y. Hashikawa and

Y. Murata, Asian J. Org. Chem., 2022, 11, e202200357;

(d) Y. Hashikawa, N. Fujikawa, S. Okamoto and Y. Murata, Dalton

Trans., 2022, 51, 17804–17808; (e) Y. Hashikawa, S. Sadai,

S. Okamoto and Y. Murata, Angew. Chem., Int. Ed., 2023,

62, e202215380.

´dard, A. Vlassova, A. C. Hernandez-Perez, A. Bes-sette,

13 (a) A.-C. Be

G. S. Hanan, M. A. Heuft and S. K. Collins, Chem. – Eur. J., 2013, 19,

ˇ´nsky

´ and

16295–16302; (b) M. Drac

´, J. Storch, V. Cı´rkva, I. Cı´sarˇova

J. Sy´kora, Phys. Chem. Chem. Phys., 2017, 19, 2900–2907.

14 J. Ohtaka, T. Sakamoto and Y. Kikugawa, Tetrahedron Lett., 2009, 50,

1681–1683.

15 (a) K. Kurotobi and Y. Murata, Science, 2011, 333, 613–616;

(b) Y. Hashikawa, M. Murata, A. Wakamiya and Y. Murata, J. Am.

Chem. Soc., 2017, 139, 16350–16358.

16 (a) Y. Hashikawa and Y. Murata, Chem. Sci., 2020, 11, 12428–12435;

(b) Y. Hashikawa, S. Okamoto and Y. Murata, Chem. – Eur. J., 2021,

27, 4864–4868; (c) Y. Hashikawa, H. Kawasaki and Y. Murata,

Organometallics, 2022, 41, 354–359.

Chem. Commun., 2023, 59, 6560–6563 | 6563

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