Structural Manipulation of Benzofulvene Derivatives Showing Spontaneous Thermoreversible Polymerization. Role of the Substituents in the Modulation of Polymer Properties
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文摘
The synthesis of a series of benzofulvene derivatives 3 related to the recently studied ethyl1-methylene-3-(4-methylphenyl)-1H-indene-2-carboxylate (BF1) is described. The properties of these trans-dienederivatives were characterized with regard to their capability of polymerizing spontaneously to give new polymersbased on functionalized indene monomeric units. The series of polymers has been investigated by NMRspectroscopy, multiangle light scattering online to size exclusion chromatography, UV-vis spectroscopy, massspectrometry, differential scanning calorimetry, and scanning electron microscopy. The new polymers show veryinteresting properties such as a thermoreversible polymerization/depolymerization, a variable degree of ges/gifchars/pi.gif" BORDER=0 >-stacking,a tendency to give nanostructured macromolecular aggregates, and a high solubility in the most common organicsolvents. Remarkably, this study demonstrated that most of the polymer properties (e.g. formation, molecularweight, structure, thermoreversibility, and aggregation in nanostructured entities) may be modulated by thestereoelectronic characteristics of the substituents present on the indene moiety.

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