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NMR Spectroscopic Study of the Self-Aggregation of 3-Hexen-1,5-diyne Derivatives

Authors

  • Dr. Ana Pérez,

    1. Instituto de Nanociencia de Aragón, Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Zaragoza, 50009 Zaragoza (Spain)
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  • Dr. Diana de Saá,

    1. Departamento de Química Orgánica e Inorgánica and Instituto Universitario de Química Organometálica, “Enrique Moles,” Unidad Asociada al CSIC. Universidad de Oviedo, c/ Julián Clavería, 8, 33006 Oviedo (Spain)
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  • Prof. Alfredo Ballesteros,

    1. Departamento de Química Orgánica e Inorgánica and Instituto Universitario de Química Organometálica, “Enrique Moles,” Unidad Asociada al CSIC. Universidad de Oviedo, c/ Julián Clavería, 8, 33006 Oviedo (Spain)
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  • Prof. José Luis Serrano,

    1. Instituto de Nanociencia de Aragón, Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Zaragoza, 50009 Zaragoza (Spain)
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  • Dr. Teresa Sierra,

    1. Instituto de Ciencia de Materiales de Aragón, Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Zaragoza CSIC, 50009 Zaragoza (Spain), Fax: (+34) 976-76-26-86
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  • Dr. Pilar Romero

    Corresponding author
    1. Instituto de Ciencia de Materiales de Aragón, Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Zaragoza CSIC, 50009 Zaragoza (Spain), Fax: (+34) 976-76-26-86
    • Instituto de Ciencia de Materiales de Aragón, Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Zaragoza CSIC, 50009 Zaragoza (Spain), Fax: (+34) 976-76-26-86

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Abstract

The self-assembly of polycatenar molecules derived from 1,6-diphenyl-3,4-dipropyl-3-hexen-1,5-diyne has been studied in detail by solution NMR spectroscopy. The analysis of the concentration- and temperature-dependent evolution of the chemical shifts and the diffusion coefficients in [D12]cyclohexane agrees well with an isodesmic model of association in this solvent. The association constants for the stacking and entropy and enthalpy of the process have been obtained. The driving force for the aggregation process is provided by a negative enthalpy (ΔH), which is partially compensated by a negative entropy (ΔS). A structural study of the self-assembly in solution has been carried out with the help of NOESY NMR spectroscopic experiments.

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