Strong Stacking between F⋅⋅⋅H[BOND]N Hydrogen-Bonded Foldamers and Fullerenes: Formation of Supramolecular Nano Networks

Authors

  • Chuang Li,

    1. State Key Laboratory of Bio-Organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China, Fax: (+86) 21-6416 6128
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  • Yuan-Yuan Zhu,

    1. State Key Laboratory of Bio-Organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China, Fax: (+86) 21-6416 6128
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  • Hui-Ping Yi,

    1. State Key Laboratory of Bio-Organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China, Fax: (+86) 21-6416 6128
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  • Chang-Zhi Li,

    1. State Key Laboratory of Bio-Organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China, Fax: (+86) 21-6416 6128
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  • Xi-Kui Jiang Prof. Dr.,

    1. State Key Laboratory of Bio-Organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China, Fax: (+86) 21-6416 6128
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  • Zhan-Ting Li Prof. Dr.,

    1. State Key Laboratory of Bio-Organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China, Fax: (+86) 21-6416 6128
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  • Yi-Hua Yu Prof.

    1. Key Laboratory of Optical and Magnetic Resonance Spectroscopy, Ministry of Education, East China Normal University, Shanghai 200062, China
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Abstract

The stacking interactions between F⋅⋅⋅H[BOND]N hydrogen-bonded foldamers 13, bis-foldamer 4, and tris-foldamer 5 and C60 and C70 are described. Compound 4 contains two folded units, which are connected by an isophthalamide linker, whereas 5 has a C3-symmetrical discotic structure, in which three folded units are connected by a benzene-1,3,5-tricarboxamide unit. UV/Vis, fluorescence, and NMR experiments have revealed that the foldamers or folded units strongly stack with fullerenes in chloroform. The (apparent) association constants of the respective complexes have been determined by a fluorescence titration method. The strong association is tentatively attributed to intermolecular cooperative fluorophenyl⋅⋅⋅π and solvophobic interactions. A similar but weaker interaction has also been observed between an MeO⋅⋅⋅H[BOND]N hydrogen-bonded foldamer and fullerenes. AFM studies have revealed that the surfaces of 3 and 4 show fibrous networks, while the surface of 5 shows particles. In sharp contrast, mixtures of 3 and 4 with C60 have been shown to generate thinner separated fibrils, whereas a mixture of 5 and C60 produces honeycomb-like nano networks, for which a columnar cooperative stacking pattern is proposed. The results demonstrate the usefulness of F⋅⋅⋅H[BOND]N hydrogen-bonded folded structures in the construction of nanoscaled materials.

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