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Issue 2, 2015
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Molecular recognition in curved π-systems: effects of π-lengthening of tubular molecules on thermodynamics and structures

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Abstract

The thermodynamics and molecular structure of a supramolecular complex between a tubular molecule, (P)-(12,8)-[4]cyclo-2,8-anthanthrenylene, and fullerene were investigated. The enthalpy-driven characteristics of the association were enhanced upon lengthening of the curved sp2-carbon networks in the tubular molecule as a result of an increase in the C–C contact areas in addition to the emergence of CH–π contacts with aliphatic chains. The involvement of CH–π interactions in the molecular recognition consequently increased the entropy cost for the association, and the importance of molecular structures at the edge of tubular molecules was revealed. An inflection-free, smooth surface inside the tubular molecule was revealed by crystallographic analysis, which allowed for dynamic motions of the encapsulated fullerene molecule in solution. This study provided a new example of a molecular peapod with a smoothly curved π-interface to be examined in the structure–thermodynamics relationship study and led to an in-depth understanding of peapods in general.

Graphical abstract: Molecular recognition in curved π-systems: effects of π-lengthening of tubular molecules on thermodynamics and structures

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Publication details

The article was received on 13 Sep 2014, accepted on 12 Oct 2014 and first published on 14 Oct 2014


Article type: Edge Article
DOI: 10.1039/C4SC02812K
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Citation: Chem. Sci., 2015,6, 909-916
  • Open access: Creative Commons BY-NC license
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    Molecular recognition in curved π-systems: effects of π-lengthening of tubular molecules on thermodynamics and structures

    T. Matsuno, S. Sato, R. Iizuka and H. Isobe, Chem. Sci., 2015, 6, 909
    DOI: 10.1039/C4SC02812K

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