Abstract
New 3D conformers were synthesized to show a nanomolecular configuration with geometrically branched 2-diphenylaminofluorene (DPAF-C2M) chromophores using a symmetrical 1,3,5-triaminobenzene ring as the center core for the connection of three fused DPAF-C2M moieties. The design led to a class of cis-cup-tris[(DPAF-C2M)-C60(>DPAF-C9)] 3D conformers with three bisadduct-analogous <C60> cages per nanomolecule facing at the same side of the geometrical molecular cis-cup-shape structure. A sequential synthetic route was described to afford this 3D configurated conformer in a high yield with various spectroscopic characterizations. In principle, a nanostructure with a non-coplanar 3D configuration in design should minimize the direct contact or π-stacking of fluorene rings with each other during molecular packing to the formation of fullerosome array. It may also prevent the self-quenching effect of its photoexcited states in solids. Photophysical properties of this cis-cup-conformer were also investigated.
Highlights
Photoinduced intramolecular energy and electron transfer phenomena in organo [60]fullerene derivatives having a covalent molecular composition of both an electron donor and a [60]fullerenyl or nanocarbon acceptor components were demonstrated over a number of years [1,2,3]
Responsive nanophotonic physical properties of 3D conformers tris[(DPAF-C2M )C60 (>DPAF-C9 )] (4-C2M−9 ) are achievable by associating a donor–acceptor type chemical structure to a photomechanism having the ability to create a largely enhanced intramolecular energy and electron transfer efficiency. This mechanism occurs between C60 > acceptor and DPAF-C2M /and DPAF-C9 donor moieties bonded on fullerenes
This revealed the successful utilization of stereochemistry to allow hindered and branched 30,50,50 -trimethylhexyl (C9 ) arms to maintain the space-separation of three planar DPAF moieties intramolecularly within the nanostructure
Summary
Photoinduced intramolecular energy and electron transfer phenomena in organo [60]fullerene derivatives having a covalent molecular composition of both an electron donor and a [60]fullerenyl or nanocarbon acceptor components were demonstrated over a number of years [1,2,3]. Similar photophysical chemistry was simulated in the modulation of photoswitchable dielectric properties to observe a large amplification of dielectric constants in a material combination form of multi-layered core-shell nanoparticles (NPs) [27,28,29]. The latter system was based on photoinduced intramolecular electronic charge-polarization of light-harvesting chromophoric nano[60]fullerenyl conjugates, such as 9,9-di(3,5,5-trimethylhexyl)-2-diphenylaminofluorenyl-methano[60]fullerene. C60> cage making it possible to rapidly shift an electron from light-harvesting DPAF were based on the high electronegativity of C60 > cage making it possible to rapidly shift an electron (diphenylaminofluorene) donor moiety within the molecular structure to the C60> moiety.
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