Toward Möbius and Tubular Cyclopolyarene Nanorings via Arylbutadiyne Macrocycles
Zhouyang Luo
Beijing National Laboratory for Molecular Sciences, Centre for Soft Matter Science and Engineering, Key Lab of Polymer Chemistry & Physics of the Ministry of Education, College of Chemistry, Peking University, Beijing, 100871 China
These authors contributed equally to this work.
Search for more papers by this authorXiao Yang
Beijing National Laboratory for Molecular Sciences, Centre for Soft Matter Science and Engineering, Key Lab of Polymer Chemistry & Physics of the Ministry of Education, College of Chemistry, Peking University, Beijing, 100871 China
These authors contributed equally to this work.
Search for more papers by this authorKang Cai
Beijing National Laboratory for Molecular Sciences, Centre for Soft Matter Science and Engineering, Key Lab of Polymer Chemistry & Physics of the Ministry of Education, College of Chemistry, Peking University, Beijing, 100871 China
Search for more papers by this authorXiangyu Fu
Beijing National Laboratory for Molecular Sciences, Centre for Soft Matter Science and Engineering, Key Lab of Polymer Chemistry & Physics of the Ministry of Education, College of Chemistry, Peking University, Beijing, 100871 China
Search for more papers by this authorDi Zhang
Beijing National Laboratory for Molecular Sciences, Centre for Soft Matter Science and Engineering, Key Lab of Polymer Chemistry & Physics of the Ministry of Education, College of Chemistry, Peking University, Beijing, 100871 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Yuguo Ma
Beijing National Laboratory for Molecular Sciences, Centre for Soft Matter Science and Engineering, Key Lab of Polymer Chemistry & Physics of the Ministry of Education, College of Chemistry, Peking University, Beijing, 100871 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Dahui Zhao
Beijing National Laboratory for Molecular Sciences, Centre for Soft Matter Science and Engineering, Key Lab of Polymer Chemistry & Physics of the Ministry of Education, College of Chemistry, Peking University, Beijing, 100871 China
Search for more papers by this authorZhouyang Luo
Beijing National Laboratory for Molecular Sciences, Centre for Soft Matter Science and Engineering, Key Lab of Polymer Chemistry & Physics of the Ministry of Education, College of Chemistry, Peking University, Beijing, 100871 China
These authors contributed equally to this work.
Search for more papers by this authorXiao Yang
Beijing National Laboratory for Molecular Sciences, Centre for Soft Matter Science and Engineering, Key Lab of Polymer Chemistry & Physics of the Ministry of Education, College of Chemistry, Peking University, Beijing, 100871 China
These authors contributed equally to this work.
Search for more papers by this authorKang Cai
Beijing National Laboratory for Molecular Sciences, Centre for Soft Matter Science and Engineering, Key Lab of Polymer Chemistry & Physics of the Ministry of Education, College of Chemistry, Peking University, Beijing, 100871 China
Search for more papers by this authorXiangyu Fu
Beijing National Laboratory for Molecular Sciences, Centre for Soft Matter Science and Engineering, Key Lab of Polymer Chemistry & Physics of the Ministry of Education, College of Chemistry, Peking University, Beijing, 100871 China
Search for more papers by this authorDi Zhang
Beijing National Laboratory for Molecular Sciences, Centre for Soft Matter Science and Engineering, Key Lab of Polymer Chemistry & Physics of the Ministry of Education, College of Chemistry, Peking University, Beijing, 100871 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Yuguo Ma
Beijing National Laboratory for Molecular Sciences, Centre for Soft Matter Science and Engineering, Key Lab of Polymer Chemistry & Physics of the Ministry of Education, College of Chemistry, Peking University, Beijing, 100871 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Dahui Zhao
Beijing National Laboratory for Molecular Sciences, Centre for Soft Matter Science and Engineering, Key Lab of Polymer Chemistry & Physics of the Ministry of Education, College of Chemistry, Peking University, Beijing, 100871 China
Search for more papers by this authorDedicated to Professor Youqi Tang on the occasion of his 100th birthday
Abstract
By harnessing a highly efficient metal-catalyzed tandem cycloaddition reaction as the key benzannulation step, a series of cyclopolyarene nanorings of varied sizes are obtained from poly(arylene-butadiynylene) macrocyclic precursors, which can be synthesized relatively conveniently. Interestingly, due to the nonparallel bond connectivity of the repeat unit, unique Möbius topology is manifested by the cyclopolyarene nanorings composed of an odd number of repeat units, whereas cylindrical tubular structures with radial conjugation are formed with those consisting of an even number of repeat units.
Conflict of interest
The authors declare no conflict of interest.
Supporting Information
As a service to our authors and readers, this journal provides supporting information supplied by the authors. Such materials are peer reviewed and may be re-organized for online delivery, but are not copy-edited or typeset. Technical support issues arising from supporting information (other than missing files) should be addressed to the authors.
| Filename | Description |
|---|---|
| ange202003538-sup-0001-misc_information.cif65.2 KB | Supplementary |
| ange202003538-sup-0001-misc_information.pdf3.8 MB | Supplementary |
Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.
References
- 1X.-Y. Wang, A. Narita, K. Müllen, Nat. Rev. Chem. 2017, 2, 0100.
- 2
- 2aM. R. Golder, R. Jasti, Acc. Chem. Res. 2015, 48, 557–566;
- 2bH. Omachi, Y. Segawa, K. Itami, Acc. Chem. Res. 2012, 45, 1378–1389;
- 2cE. R. Darzi, R. Jasti, Chem. Soc. Rev. 2015, 44, 6401–6410;
- 2dE. S. Hirst, R. Jasti, J. Org. Chem. 2012, 77, 10473–10478;
- 2eS. E. Lewis, Chem. Soc. Rev. 2015, 44, 2221–2304;
- 2fA. F. Tran-Van, H. A. Wegner, Beilstein J. Nanotechnol. 2014, 5, 1320–1333;
- 2gA. Pérez-Guardiola, M. E. Sandoval-Salinas, D. Casanova, E. San-Fabián, A. J. Pérez-Jiménez, J. C. Sancho-García, Phys. Chem. Chem. Phys. 2018, 20, 7112–7124;
- 2hY. Xu, B. Wang, R. Kaur, M. B. Minameyer, M. Bothe, T. Drewello, D. M. Guldi, M. von Delius, Angew. Chem. Int. Ed. 2018, 57, 11549–11553; Angew. Chem. 2018, 130, 11723–11727.
- 3
- 3aR. Jasti, J. Bhattacharjee, J. B. Neaton, C. R. Bertozzi, J. Am. Chem. Soc. 2008, 130, 17646–17647;
- 3bJ. L. Xia, R. Jasti, Angew. Chem. Int. Ed. 2012, 51, 2474–2476; Angew. Chem. 2012, 124, 2524–2526;
- 3cT. J. Sisto, X. Tian, R. Jasti, J. Org. Chem. 2012, 77, 5857–5860.
- 4
- 4aY. Segawa, S. Miyamoto, H. Omachi, S. Matsuura, P. Senel, T. Sasamori, N. Tokitoh, K. Itami, Angew. Chem. Int. Ed. 2011, 50, 3244–3248; Angew. Chem. 2011, 123, 3302–3306;
- 4bY. Segawa, A. Yagi, K. Itami, Phys. Sci. Rev. 2017, 2, 20160102.
- 5
- 5aE. Kayahara, L. S. Sun, H. Onishi, K. Suzuki, T. Fukushima, A. Sawada, H. Kaji, S. Yamago, J. Am. Chem. Soc. 2017, 139, 18480–18483;
- 5bS. Yamago, Y. Watanabe, T. Iwamoto, Angew. Chem. Int. Ed. 2010, 49, 757–759; Angew. Chem. 2010, 122, 769–771;
- 5cT. Iwamoto, Y. Watanabe, Y. Sakamoto, T. Suzuki, S. Yamago, J. Am. Chem. Soc. 2011, 133, 8354–8361;
- 5dY. Segawa, A. Fukazawa, S. Matsuura, H. Omachi, S. Yamaguchi, S. Irle, K. Itami, Org. Biomol. Chem. 2012, 10, 5979–5984.
- 6
- 6aS. Hitosugi, T. Yamasaki, H. Isobe, J. Am. Chem. Soc. 2012, 134, 12442–12445;
- 6bS. Hitosugi, W. Nakanishi, T. Yamasaki, H. Isobe, Nat. Commun. 2011, 2, 492.
- 7
- 7aA. Yagi, G. Venkataramana, Y. Segawa, K. Itami, Chem. Commun. 2014, 50, 957–959;
- 7bT. Iwamoto, E. Kayahara, N. Yasuda, T. Suzuki, S. Yamago, Angew. Chem. Int. Ed. 2014, 53, 6430–6434; Angew. Chem. 2014, 126, 6548–6552.
- 8
- 8aT. Nishiuchi, X. L. Feng, V. Enkelmann, M. Wagner, K. Mullen, Chem. Eur. J. 2012, 18, 16621–16625;
- 8bM. Quernheim, F. E. Golling, W. Zhang, M. Wagner, H. J. Rader, T. Nishiuchi, K. Mullen, Angew. Chem. Int. Ed. 2015, 54, 10341–10346; Angew. Chem. 2015, 127, 10482–10487;
- 8cG. Povie, Y. Segawa, T. Nishihara, Y. Miyauchi, K. Itami, J. Am. Chem. Soc. 2018, 140, 10054–10059;
- 8dZ. Sun, K. Ikemoto, T. M. Fukunaga, T. Koretsune, R. Arita, S. Sato, H. Isobe, Science 2019, 363, 151–154.
- 9
- 9aS. Lee, E. Chénard, D. L. Gray, J. S. Moore, J. Am. Chem. Soc. 2016, 138, 13814–13817;
- 9bN. Hayase, Y. Miyauchi, Y. Aida, H. Sugiyama, H. Uekusa, Y. Shibata, K. Tanaka, Org. Lett. 2017, 19, 2993–2996.
- 10
- 10aJ. S. Wu, L. Gherghel, M. D. Watson, J. X. Li, Z. H. Wang, C. D. Simpson, U. Kolb, K. Mullen, Macromolecules 2003, 36, 7082–7089;
- 10bM. B. Goldfinger, T. M. Swager, J. Am. Chem. Soc. 1994, 116, 7895–7896;
- 10cJ. D. Tovar, T. M. Swager, J. Organomet. Chem. 2002, 653, 215–222.
- 11
- 11aN. Asao, T. Nogami, S. Lee, Y. Yamamoto, J. Am. Chem. Soc. 2003, 125, 10921–10925;
- 11bX. Yang, L. Yuan, Z. Chen, Z. Liu, Q. Miao, Org. Lett. 2018, 20, 6952–6956.
- 12
- 12aS. J. Hein, D. Lehnherr, H. Arslan, F. J. Uribe-Romo, W. R. Dichtel, Acc. Chem. Res. 2017, 50, 2776–2788;
- 12bH. Arslan, F. J. Uribe-Romo, B. J. Smith, W. R. Dichtel, Chem. Sci. 2013, 4, 3973–3978;
- 12cH. Arslan, J. D. Saathoff, D. N. Bunck, P. Clancy, W. R. Dichtel, Angew. Chem. Int. Ed. 2012, 51, 12051–12054; Angew. Chem. 2012, 124, 12217–12220;
- 12dD. Lehnherr, C. Chen, Z. Pedramrazi, C. R. DeBlase, J. M. Alzola, I. Keresztes, E. B. Lobkovsky, M. F. Crommie, W. R. Dichtel, Chem. Sci. 2016, 7, 6357–6364.
- 13
- 13aT. Kawase, M. Oda, Angew. Chem. Int. Ed. 2004, 43, 4396–4398; Angew. Chem. 2004, 116, 4496–4498;
- 13bH. S. Rzepa, Chem. Rev. 2005, 105, 3697–3715.
- 14D. M. Walba, R. M. Richards, R. C. Haltiwanger, J. Am. Chem. Soc. 1982, 104, 3219–3221.
- 15
- 15aP. M. Warner, J. Org. Chem. 2006, 71, 9271–9282;
- 15bC. Castro, Z. Chen, C. S. Wannere, H. Jiao, W. L. Karney, M. Mauksch, R. Puchta, N. J. R. van Eikema Hommes, P. v. R. Schleyer, J. Am. Chem. Soc. 2005, 127, 2425–2432;
- 15cR. Gleiter, B. Esser, S. C. Kornmayer, Acc. Chem. Res. 2009, 42, 1108–1116;
- 15dD. Ajami, O. Oeckler, A. Simon, R. Herges, Nature 2003, 426, 819–821;
- 15eC. Zhu, M. Luo, Q. Zhu, J. Zhu, P. v. R. Schleyer, J. I. C. Wu, X. Lu, H. Xia, Nat. Commun. 2014, 5, 3265.
- 16M. Stępień, L. Latos-Grażyński, N. Sprutta, P. Chwalisz, L. Szterenberg, Angew. Chem. Int. Ed. 2007, 46, 7869–7873; Angew. Chem. 2007, 119, 8015–8019.
- 17
- 17aY. Tanaka, S. Saito, S. Mori, N. Aratani, H. Shinokubo, N. Shibata, Y. Higuchi, Z. S. Yoon, K. S. Kim, S. B. Noh, J. K. Park, D. Kim, A. Osuka, Angew. Chem. Int. Ed. 2008, 47, 681–684; Angew. Chem. 2008, 120, 693–696;
- 17bT. Tanaka, T. Sugita, S. Tokuji, S. Saito, A. Osuka, Angew. Chem. Int. Ed. 2010, 49, 6619–6621; Angew. Chem. 2010, 122, 6769–6771;
- 17cH. Ruffin, G. Nyame Mendendy Boussambe, T. Roisnel, V. Dorcet, B. Boitrel, S. Le Gac, J. Am. Chem. Soc. 2017, 139, 13847–13857.
- 18
- 18aG. R. Schaller, F. Topić, K. Rissanen, Y. Okamoto, J. Shen, R. Herges, Nat. Chem. 2014, 6, 608–613;
- 18bG. Naulet, L. Sturm, A. Robert, P. Dechambenoit, F. Röhricht, R. Herges, H. Bock, F. Durola, Chem. Sci. 2018, 9, 8930–8936.
- 19S. Nishigaki, Y. Shibata, A. Nakajima, H. Okajima, Y. Masumoto, T. Osawa, A. Muranaka, H. Sugiyama, A. Horikawa, H. Uekusa, H. Koshino, M. Uchiyama, A. Sakamoto, K. Tanaka, J. Am. Chem. Soc. 2019, 141, 14955–14960.
- 20
- 20aJ. M. Lim, J.-Y. Shin, Y. Tanaka, S. Saito, A. Osuka, D. Kim, J. Am. Chem. Soc. 2010, 132, 3105–3114;
- 20bK. S. Kim, Z. S. Yoon, A. B. Ricks, J.-Y. Shin, S. Mori, J. Sankar, S. Saito, Y. M. Jung, M. R. Wasielewski, A. Osuka, D. Kim, J. Phys. Chem. A 2009, 113, 4498–4506.
- 21M. M. Haley, M. L. Bell, J. J. English, C. A. Johnson, T. J. R. Weakley, J. Am. Chem. Soc. 1997, 119, 2956–2957.
- 22S. Chen, Q. Yan, T. Li, D. Zhao, Org. Lett. 2010, 12, 4784–4787.
Citing Literature
This is the
German version
of Angewandte Chemie.
Note for articles published since 1962:
Do not cite this version alone.
Take me to the International Edition version with citable page numbers, DOI, and citation export.
We apologize for the inconvenience.
