Fullerodendrimers: Fullerene-Containing Macromolecules with Intriguing Properties

Abstract

Fullerenes possess electronic and photophysical properties which make them natural candidates for the preparation of functional dendrimers. The attachment of a controlled number of dendrons on a C(60) core provides a compact insulating layer around the carbon sphere, and the triplet lifetimes of the C(60) chromophore can be used to evaluate its degree of isolation from external contacts. The fullerene core can also act as a terminal energy receptor in dendrimer-based light-harvesting systems. When a fullerodendrimer is further functionalized with a suitable electron donor, it may exhibit the essential features of a multicomponent artificial photosynthetic system in which photo-induced energy transfer from the antenna to the C(60) core is followed by electron transfer. On the other hand, the preparation of dendrons with peripheral C(60) subunits or containing a C(60) sphere at each branching unit has been achieved. These fullerodendrons are not only interesting building blocks for the synthesis of monodisperse fullerene-rich macromolecules with intriguing properties, but they are also amphiphilic compounds capable of forming stable Langmuir films at the air-water interface.

Dendritic encapsulation of active core molecules

“…fullerodendrimers, is currently an area of considerable interest [14][15][16][17]. In particular, the unusual chemical and physical properties of fullerene derivatives make fullerodendrimers attractive candidates for a variety of interesting features in supramolecular chemistry and materials science [18][19][20][21][22].…”

Synthetic Strategies towards Fullerene-Rich Dendrimer Assemblies

“…The reaction conditions for the cyclotrimerization were first optimized for the lowest generation alkyne 43. The choice of Co 2 (CO) 8 as catalyst was key to this synthesis. Indeed, it turned out that Co 2 (CO) 8 efficiently catalyzed the cyclisation of three molecules of bisaryl alkynes under formation of a hexaphenylbenzene core.…”

“…The choice of Co 2 (CO) 8 as catalyst was key to this synthesis. Indeed, it turned out that Co 2 (CO) 8 efficiently catalyzed the cyclisation of three molecules of bisaryl alkynes under formation of a hexaphenylbenzene core. Under optimized conditions, treatment of 43 with a catalytic amount of Co 2 (CO) 8 in dioxane at room temperature for 24 h afforded 46 in 93% yield.…”

“…Indeed, it turned out that Co 2 (CO) 8 efficiently catalyzed the cyclisation of three molecules of bisaryl alkynes under formation of a hexaphenylbenzene core. Under optimized conditions, treatment of 43 with a catalytic amount of Co 2 (CO) 8 in dioxane at room temperature for 24 h afforded 46 in 93% yield. The same conditions were then used for the preparation of the higher generation compounds.…”

“…Since then, the field of fullerodendrimers has generated significant research activities with new materials that exhibited intriguing properties [6][7][8][9][10][11][12]. Particularly, the peculiar physical properties of fullerene derivatives make fullerodendrimers attractive candidates for a variety of interesting features in supramolecular chemistry and materials science [9].…”