Synthesis of Open-Cage Fullerenes with a Long Tail

Hao Zhang; Jie Su; Liangbing Gan

doi:10.1055/s-0040-1718520

Organic Materials, Inhaltsverzeichnis

CC BY-NC-ND 4.0 · Organic Materials 2020; 02(04): 282-287
DOI: 10.1055/s-0040-1718520

Focus Issue: Curved Organic π-Systems

Original Article

Synthesis of Open-Cage Fullerenes with a Long Tail

Authors

Hao Zhang

^aBeijing National Laboratory for Molecular Sciences, Key Laboratory of Bioorganic Chemistry and Molecular Engineering of the Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing, China
Jie Su

^aBeijing National Laboratory for Molecular Sciences, Key Laboratory of Bioorganic Chemistry and Molecular Engineering of the Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing, China
Liangbing Gan

^aBeijing National Laboratory for Molecular Sciences, Key Laboratory of Bioorganic Chemistry and Molecular Engineering of the Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing, China

Abstract

Alle Artikel dieser Rubrik

Abstract

To explore potential applications for open-cage fullerenes, we employed 4-((6-bromohexyl)oxy)aniline to react with an open-cage fullerene precursor which has an 11-membered orifice and prepared open-cage fullerenes with an 18-membered orifice. The bromo atom at the end of the hexyl chain in these open-cage compounds could be easily replaced by alkoxyl groups to further extend the linear chain. The results also show that the presence of the alkyl chain slightly changes the reactivity of the orifice-expansion reaction.

Key words

fullerene - open-cage - amphiphilic

Volltext

Referenzen

References

1a Hirsch A, Brettreich M. Fullerenes: Chemistry and Reactions. Wiley-VCH: Weinheim; 2005
1b Thilgen C, Diederich F. Chem. Rev. 2006; 106: 5049

2 For example the “fullerene sugar balls”: (a) Nierengarten, J.-F.; Iehl, J.; Oerthel, V.; Holler, M.; Illescas, B. M.; Munoz, A.; Martin, N.; Rojo, J.; Sanchez-Navarro, M.; Cecioni, S.; Vidal, S.; Buffet, K.; Durka, M.; Vincent, S. P. Chem. Commun. 2010, 46, 3860. (b) Muñoz, A.; Sigwalt, D.; Illescas, B. M.; Luczkowiak, J.; Rodríguez-Perez, L.; Nierengarten, I.; Holler, M.; Remy, J.-S.; Buffet, K.; Vincent, S. P.; Rojo, J.; Delgado, R.; Nierengarten, J.-F.; Martín, N. Nat. Chem. 2016, 8, 50. (c) Ramos-Soriano, J.; Reina, J. J.; Illescas, B. M.; de la Cruz, N.; Rodriguez-Perez, L.; Lasala, F.; Rojo, J.; Delgado, R.; Martin, N. S. J. Am. Chem. Soc. 2019; 141: 15403

3a Xie Q, Perez-Cordero E, Echegoyen L. J. Am. Chem. Soc. 1992; 114: 3978
3b Hummelen JC, Knight BW, Lepeq F, Wudl F, Yao J, Wilkins CL. J. Org. Chem. 1995; 60: 532
3c He Y, Chen HY, Hou J, Li Y. J. Am. Chem. Soc. 2010; 132: 1377
3d Umeyama T, Imahori H. Acc. Chem. Res. 2019; 52: 2046

4a Zheng M, Li F, Shi Z, Gao X, Kadish KM. J. Org. Chem. 2007; 72: 2538
4b Li YB, Xu D, Gan LB. Angew. Chem. Int. Ed. 2016; 55: 2483
4c Kosaya MP, Rybalchenko AV, Lukonina NS, Mazaleva ON, Ioffe IN, Markov VY, Troyanov SI, Sidorov LN, Tamm NB, Goryunkov AA. Chem. Asian J. 2018; 13: 1920
4d Li D, Li ZJ, He FG, Geng C, Gao X. J. Org. Chem. 2019; 84: 14679
4e Liu KQ, Wang JJ, Yan XX, Niu C, Ang GW. Chem. Sci. 2020; 11: 384

5a Jehoulet C, Obeng C, Kim YT, Zhou F, Bard AJ. J. Am. Chem. Soc. 1992; 114: 4237
5b Zhou DJ, Gan LB, Luo CP, Huang CH, Yao GQ, Zhao XS, Liu ZF, Xia XH, Zhang B. J. Phys. Chem. 1996; 100: 3150
5c Mezour MA, Choueiri RM, Lukoyanova O, Lennox RB, Perepichka DF. Nanoscale 2016; 8: 16955
5d Liu J, Wang Y, Jiang P, Tu G. ACS Omega 2020; 5: 1336

6a Murata M, Murata Y, Komatsu K. Chem. Commun. 2008; 46: 6083
6b Vougioukalakis GC, Roubelakis MM, Orfanopoulos M. Chem. Soc. Rev. 2010; 39: 817
6c Gan L, Yang D, Zhang Q, Huang H. Adv. Mater. 2010; 22: 1498

7 Shi LJ, Gan LB. J. Phys. Org. Chem. 2013; 26: 766

8a Gan L. Chem. Rec. 2015; 15: 189
8b Gan LB. Chin. J. Chem. 2018; 36: 991
8c Gan L. Acc. Chem. Res. 2019; 52: 1793

9a Zhang Q, Jia Z, Liu S, Zhang G, Xiao Z, Yang D, Gan L, Wang Z, Li Y. Org. Lett. 2009; 11: 2772
9b Zhang H, Xu L, Gan L. ChemPlusChem 2017; 82: 1002

10 Xiao Z, Yao J, Yang D, Wang F, Huang S, Gan L, Jia Z, Jiang Z, Yang X, Zheng B, Yuan G, Zhang S, Wang Z. J. Am. Chem. Soc. 2007; 129: 16149
11 Tritto E, Chico R, Sanz-Enguita G, Folcia CL, Ortega J, Coco S, Espinet P. Inorg. Chem. 2014; 53: 3449

12a Homma T, Harano K, Isobe H, Nakamura E. Angew. Chem. Int. Ed. 2010; 49: 1665
12b Zhang G, Liu Y, Liang DH, Gan LB, Li YL. Angew. Chem. Int. Ed. 2010; 49: 5293
12c Kraft A, Roth P, Schmidt D, Stangl J, Müller-Buschbaum K, Beuerle F. Chemistry 2016; 22: 5982
12d Nitta H, Harano K, Isomura M, Backus EH. G, Bonn M, Nakamura E. J. Am. Chem. Soc. 2017; 139: 7677

Zusatzmaterial

Ergänzendes Material (PDF)