Abstract

A hybrid nanohoop molecule composed of anthanthrenylene and phenylene panels was synthesized. Structural analysis by NMR spectroscopy revealed the synchronous dynamics of the arylene panels in solution. Theoretical calculations further clarified the molecular structures involved in the dynamics and showed correlated rotations of neighboring arylene panels.

References

1) a)

R. Jasti, J. Bhattacharjee, J. B. Neaton, C. R. Bertozzi, J. Am. Chem. Soc.  2008, 130, 17646.

b)

H. Takaba, H. Omachi, Y. Yamamoto, J. Bouffard, K. Itami, Angew. Chem., Int. Ed.  2009, 48, 6112.

c)

S. Yamago, Y. Watanabe, T. Iwamoto, Angew. Chem., Int. Ed.  2010, 49, 757.

2)

S. E. Lewis, Chem. Soc. Rev.  2015, 44, 2221.

3) a)

Y. Segawa, H. Omachi, K. Itami, Org. Lett.  2010, 12, 2262.

b)

H. Omachi, Y. Segawa, K. Itami, Org. Lett.  2011, 13, 2480.

4)

T. Nishiuchi, X. Feng, V. Enkelmann, M. Wagner, K. Müllen, Chem.—Eur. J.  2012, 18, 16621.

5)

C. Huang, Y. Huang, N. G. Akhmedov, B. V. Popp, J. L. Petersen, K. K. Wang, Org. Lett.  2014, 16, 2672.

6)

T. Matsuno, H. Naito, S. Hitosugi, S. Sato, M. Kotani, H. Isobe, Pure Appl. Chem.  2014, 86, 489.

7) a)

S. Hitosugi, W. Nakanishi, T. Yamasaki, H. Isobe, Nat. Commun.  2011, 2, Article number: 492.

b)

S. Hitosugi, T. Yamasaki, H. Isobe, J. Am. Chem. Soc.  2012, 134, 12442.

8)

T. Matsuno, S. Kamata, S. Hitosugi, H. Isobe, Chem. Sci.  2013, 4, 3179.

9)

S. Hitosugi, W. Nakanishi, H. Isobe, Chem.—Asian J.  2012, 7, 1550.

10)

Z. Sun, P. Sarkar, T. Suenaga, S. Sato, H. Isobe, Angew. Chem., Int. Ed.  2015, Early View. doi:10.1002/anie.201506424.

11) a)

K. Mislow, Acc. Chem. Res.  1976, 9, 26.

b)

M. Oki, The Chemistry of Rotational Isomers, Springer, New York, 1993. doi:10.1007/978-3-642-51024-3.

12) a)

H. Omachi, S. Matsuura, Y. Segawa, K. Itami, Angew. Chem., Int. Ed.  2010, 49, 10202.

b)

Y. Ishii, Y. Nakanishi, H. Omachi, S. Matsuura, K. Matsui, H. Shinohara, Y. Segawa, K. Itami, Chem. Sci.  2012, 3, 2340.

c)

A. Yagi, G. Venkataramana, Y. Segawa, K. Itami, Chem. Commun.  2014, 50, 957.

13)

T. Iwamoto, Y. Watanabe, Y. Sakamoto, T. Suzuki, S. Yamago, J. Am. Chem. Soc.  2011, 133, 8354.

14)

J.-B. Giguère, Q. Verolet, J.-F. Morin, Chem.—Eur. J.  2013, 19, 372.

15)

T. Ishiyama, M. Murata, N. Miyaura, J. Org. Chem.  1995, 60, 7508.

16) a)

W. M. F. Fabian, J. Comput. Chem.  1988, 9, 369.

b)

S. Y. Hong, D. Y. Kim, C. Y. Kim, R. Hoffmann, Macromolecules  2001, 34, 6474.

17)

Note without reference.

18)

W. Nakanishi, T. Matsuno, J. Ichikawa, H. Isobe, Angew. Chem., Int. Ed.  2011, 50, 6048.

19)

J. M. Batson, T. M. Swager, Synlett  2013, 24, 2545.

20) a)

S. Sato, T. Yamasaki, H. Isobe, Proc. Natl. Acad. Sci. U.S.A.  2014, 111, 8374.

b)

T. Matsuno, S. Sato, R. Iizuka, H. Isobe, Chem. Sci.  2015, 6, 909.

21)

A. Yagi, Y. Segawa, K. Itami, J. Am. Chem. Soc.  2012, 134, 2962.

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