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The pillar [5] arene as a polyfunctional core for the development of molecular materials

Abstract : Clickable pillar[5]arene building blocks have been used for the efficient grafting of peripheral subunits onto the macrocyclic core. New liquid-crystalline pillar[5]arene derivatives have been prepared by grafting either p-dodecyloxybenzoate groups or percec-type dendrons on the macrocyclic scaffold. On the other hand, pillar[5]arene derivatives bearing peripheral porphyrin subunits have been efficiently prepared from the clickable pillar[5]arene building block and Zn(II)-porphyrin derivatives bearing a terminal alkyne function. Owing to an intramolecular complexation of the peripheral Zn(II)-porphyrin moieties by 1,2,3-triazole subunits, an original dynamic conformational equilibrium leading to a folding of the molecules has been evidenced by variable temperature 1H NMR studies. Finally, a clickable [2]rotaxane scaffold incorporating a free-base porphyrin stopper has been prepared and functionalized with ten peripheral Zn(II)-porphyrin moieties to afford a sophisticated photoactive supramolecular device.
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  • HAL Id : tel-02003453, version 1



Haifa Ben Aziza. The pillar [5] arene as a polyfunctional core for the development of molecular materials. Other. Université de Strasbourg; Université de Carthage (Tunisie), 2015. English. ⟨NNT : 2015STRAF067⟩. ⟨tel-02003453⟩



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