Synthesis of a rigid ball-and-chain donor-acceptor system through Diels-Alder functionalization of buckminsterfullerene (C[sub 60])
- Univ. of California, Los Angeles (United States)
- Univ. of New South Wales, Kensington (Australia)
Encouraged by our recent results in the functionalization of C[sub 60] through Diels-Alder reactions, we sought to develop a novel type of derivative of C[sub 60] by creating ball-and-chain systems, in which the C[sub 60] unit and another functional group, G, are attached to a rigid polycyclic chain or bridge. These systems should provide unprecedented insight into a variety of long-range intramolecular processes between C[sub 60] and G, including energy and electron transfer, and would complement the corresponding intermolecular processes studied so far. We are pleased to report the synthesis of our first ball-and-chain molecule in which the chain comprises a rigid polynorbornyl-bicyclo[2.2.0]hexyl bridge which has been used extensively by the UNSW group in the construction of several donor-bridge-acceptor systems. The key feature of the present work is the Diels-Alder reaction between C[sub 60] and a novel bridge diene affording the ball-and-chain adduct. 18 refs., 1 fig.
- OSTI ID:
- 6297578
- Journal Information:
- Journal of the American Chemical Society; (United States), Journal Name: Journal of the American Chemical Society; (United States) Vol. 115:11; ISSN JACSAT; ISSN 0002-7863
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
400102 -- Chemical & Spectral Procedures
400201* -- Chemical & Physicochemical Properties
CARBON
CHEMICAL REACTIONS
DIELS-ALDER REACTION
ELEMENTS
FULLERENES
MAGNETIC RESONANCE
MOLECULAR STRUCTURE
NONMETALS
NUCLEAR MAGNETIC RESONANCE
RESONANCE
SPECTROSCOPY
SYNTHESIS