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Article

Synthesis and Intramolecular Energy- and Electron-Transfer of 3D-Conformeric Tris(fluorenyl-[60]fullerenylfluorene) Derivatives

1
Department of Chemistry, University of Massachusetts Lowell, Lowell, MA 01854, USA
2
Functional Materials Division, AFRL/RXA, Air Force Research Laboratory, Wright-Patterson Air Force Base, Dayton, OH 45433, USA
*
Author to whom correspondence should be addressed.
Molecules 2019, 24(18), 3337; https://doi.org/10.3390/molecules24183337
Received: 3 August 2019 / Revised: 30 August 2019 / Accepted: 10 September 2019 / Published: 13 September 2019
(This article belongs to the Special Issue Materials Chemistry of Fullerenes, Graphenes and Carbon Nanotubes)
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. View Full-Text
Keywords: Tri[60]fullerenyl stereoisomers; cis-cup-form of 3D-stereoisomers; tris(diphenylaminofluorene); 3D-configurated nanostructures; intramolecular energy transfer for singlet oxygen production; intramolecular electron transfer for superoxide radical production Tri[60]fullerenyl stereoisomers; cis-cup-form of 3D-stereoisomers; tris(diphenylaminofluorene); 3D-configurated nanostructures; intramolecular energy transfer for singlet oxygen production; intramolecular electron transfer for superoxide radical production
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MDPI and ACS Style

Yin, H.; Wang, M.; Tan, L.-S.; Chiang, L.Y. Synthesis and Intramolecular Energy- and Electron-Transfer of 3D-Conformeric Tris(fluorenyl-[60]fullerenylfluorene) Derivatives. Molecules 2019, 24, 3337. https://doi.org/10.3390/molecules24183337

AMA Style

Yin H, Wang M, Tan L-S, Chiang LY. Synthesis and Intramolecular Energy- and Electron-Transfer of 3D-Conformeric Tris(fluorenyl-[60]fullerenylfluorene) Derivatives. Molecules. 2019; 24(18):3337. https://doi.org/10.3390/molecules24183337

Chicago/Turabian Style

Yin, He, Min Wang, Loon-Seng Tan, and Long Y. Chiang. 2019. "Synthesis and Intramolecular Energy- and Electron-Transfer of 3D-Conformeric Tris(fluorenyl-[60]fullerenylfluorene) Derivatives" Molecules 24, no. 18: 3337. https://doi.org/10.3390/molecules24183337

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