Bis-pseudorotaxane Formation of Perylene Bisimide-Linked [60]Fullerene Dumbbell-Like Molecules with [10]Cycloparaphenylene

Abstract

Two [60]fullerene dumbbell-like molecules with a single or double perylene-3,4,9,10-tetracarboxylic acid bisimide (PBI) linker were synthesized to study the structural and photophysical properties in addition to the complex formation with [10]cycloparaphenylene ([10]CPP). Due to their special optical properties, it is possible to describe the complexation using conventional spectroscopic methods such as NMR and fluorescence. However, isothermal titration calorimetry (ITC) was used to complete the analysis of the bis-pseudorotaxane formation by investigating the binding stoichiometries as well as the thermodynamic and kinetic parameters. It was observed that the PBI bridges do not inhibit the complexation with [10]CPP, giving rise to the formation of 1 : 1 and 1 : 2 complexes in o-dichlorobenzene with affinities of around 10⁵ · M⁻¹, similar to the [10]CPP⊃C₆₀ reference system. A novel global analysis by combination of data sets from different techniques allowed us to follow the species distribution very precisely. ITC has proven to be a very powerful method for studying the complexation between fullerene derivatives and strained carbon nanohoops, which provides not only binding affinities and stoichiometries, but also all thermodynamic and kinetic parameters of the bis-pseudorotaxane formation. These results are of significant interest for the investigation of fullerene complexes in supramolecular chemistry and for their future applications in semiconductors and optoelectronics.

Key words

supramolecular chemistry - host–guest systems - fullerenes - perylene bisimide - macrocycles - cyclophanes - carbon nanobelts

Publication History

Received: 14 June 2022

Accepted after revision: 20 July 2022

Accepted Manuscript online:
21 July 2022

Article published online:
19 August 2022

• References

• 1a Lehn J-M. Chem. Soc. Rev. 2017; 46: 2378
• 1b Lu D, Huang Q, Wang S, Wang J, Huang P, Du P. Front. Chem. 2019; 7: 668
• 2 Gokel GW, Leevy WM, Weber ME. Chem. Rev. 2004; 104: 2723
• 3 Rebek JJ. Chem. Commun. 2000; 637
• 4 Schmidt BVKJ, Hetzer M, Ritter H, Barner-Kowollik C. Prog. Polym. Sci. 2014; 39: 235
• 5 Yamago S, Kayahara E, Iwamoto T. Chem. Rev. 2014; 14: 84
• 6 Xu Y, von Delius M. Angew. Chem. Int. Ed. 2020; 59: 559
• 7 Iwamoto T, Watanabe Y, Sadahiro T, Haino T, Yamago S. Angew. Chem. Int. Ed. 2011; 50: 8342
• 8 Iwamoto T, Watanabe Y, Takaya H, Haino T, Yasuda N, Yamago S. Chem. Eur. J. 2013; 19: 14061
• 9 Ueno H, Nishihara T, Segawa Y, Itami K. Angew. Chem. Int. Ed. 2015; 54: 3707
• 10 Rio J, Beeck S, Rotas G, Ahles S, Jacquemin D, Tagmatarchis N, Ewels C, Wegner HA. Angew. Chem. Int. Ed. 2018; 57: 6930
• 11 Xu Y, Wang B, Kaur R, Minameyer MB, Bothe M, Drewello T, Guldi DM, von Delius M. Angew. Chem. Int. Ed. 2018; 57: 11549
• 12 Li K, Xu Z, Deng H, Zhou Z, Dang Y, Sun Z. Angew. Chem. Int. Ed. 2021; 60: 7649
• 13 de Juan A, Pérez EM. Nanoscale 2013; 5: 7141
• 14 Xu Y, Kaur R, Wang B, Minameyer MB, Gsänger S, Meyer B, Drewello T, Guldi DM, von Delius M. J. Am. Chem. Soc. 2018; 140: 13413
• 15 Yuan K, Zhou C-H, Zhu Y-C, Zhao X. Phys. Chem. Chem. Phys. 2015; 17: 18802
• 16 Hashimoto S, Iwamoto T, Kurachi D, Kayahara E, Yamago S. ChemPlusChem 2017; 82: 1015
• 17a Werber L, Mastai Y. Chirality 2018; 30: 619
• 17b Brown A. Int. J. Mol. Sci. 2009; 10: 3457
• 17c Matsuno T, Fujita M, Fukunaga K, Sato S, Isobe H. Nat. Commun. 2018; 9: 3779
• 18a González-Veloso I, Rodríguez-Otero J, Cabaleiro-Lago EM. Phys. Chem. Chem. Phys. 2016; 18: 31670
• 18b Oleson A, Zhu T, Dunn IS, Bialas D, Bai Y, Zhang W, Dai M, Reichman DR, Tempelaar R, Huang L, Spano FC. J. Phys. Chem. C 2019; 123: 20567
• 18c Shang X, Ahn J, Lee JH, Kim JC, Ohtsu H, Choi W, Song I, Kwak SK, Oh JH. ACS Appl. Mater. Interfaces 2021; 13: 12278
• 19a Pla S, Martín-Gomis L, Ohkubo K, Fukuzumi S, Fernández-Lázaro F, Sastre-Santos Á. Asian J. Org. Chem. 2014; 3: 185
• 19b Baffreau J, Ordronneau L, Leroy-Lhez S, Hudhomme P. J. Org. Chem. 2008; 73: 6142
• 19c Yuen JD, Pozdin VA, Young AT, Turner BL, Giles ID, Naciri J, Trammell SA, Charles PT, Stenger DA, Daniele MA. Dyes Pigm. 2020; 174: 108014
• 20 Spenst P, Würthner F. J. Photochem. Photobiol. C 2017; 31: 114
• 21a Solymosi I, Krishna S, Nuin E, Maid H, Scholz B, Guldi DM, Pérez-Ojeda ME, Hirsch A. Chem. Sci. 2021; 12: 15491
• 21b Pérez-Ojeda ME, Wabra I, Böttcher C, Hirsch A. Chem. Eur. J. 2018; 24: 14088
• 22a Sun Y, Li Z. Polym. Chem. 2017; 8: 4422
• 22b Nuin E, Lloret V, Amsharov K, Hauke F, Abellán G, Hirsch A. Chem. Eur. J. 2018; 24: 4671
• 23 Clark AE, Qin C, Li ADQ. J. Am. Chem. Soc. 2007; 129: 7586
• 24 Baffreau J, Perrin L, Leroy-Lhez S, Hudhomme P. Tetrahedron Lett. 2005; 46: 4599
• 25 Ahrens MJ, Sinks LE, Rybtchinski B, Liu W, Jones BA, Giaimo JM, Gusev AV, Goshe AJ, Tiede DM, Wasielewski MR. J. Am. Chem. Soc. 2004; 126: 8284
• 26 Hesse M, Meier H, Zeeh B. Spektroskopische Methoden in der organischen Chemie. Georg Thieme Verlag; 2005
• 27a van de Weert M, Stella L. J. Mol. Struct. 2011; 998: 144
• 27b Thordarson P. Chem. Soc. Rev. 2011; 40: 1305
• 28 Zhang X, Shi H, Zhuang G, Wang S, Wang J, Yang S, Shao X, Du P. Angew. Chem. Int. Ed. 2021; 60: 17368
• 29 Piñeiro Á, Muñoz E, Sabín J, Costas M, Bastos M, Velázquez-Campoy A, Garrido PF, Dumas P, Ennifar E, García-Río L, Rial J, Pérez D, Fraga P, Rodríguez A, Cotelo C. Anal. Biochem. 2019; 577: 117
• 30 Dumas P, Ennifar E, Da Veiga C, Bec G, Palau W, Di Primo C, Piñeiro A, Sabin J, Muñoz E, Rial J. Extending ITC to Kinetics with kinITC. Feig AL. Methods in Enzymology. 567. Cambridge: Academic Press; 2016: 157-180
• 31 Muñoz E, Sabín J, Rial J, Pérez D, Ennifar E, Dumas P, Piñeiro Á. Thermodynamic and Kinetic Analysis of Isothermal Titration Calorimetry Experiments by Using KinITC in AFFINImeter. Ennifar E. Microcalorimetry of Biological Molecules: Methods in Molecular Biology. 1964. New York, NY: Humana Press; 2019: 225-239
• 32 Kawase T, Kurata H. Chem. Rev. 2006; 106: 5250