Fullerene-Acene Chemistry: Diastereoselective Synthesis of a cis,cis-Tris[60]fullerene Adduct of 6,8,15,17-Tetraphenylheptacene

Organic Letters

Volumn 5, Issue 22, 2003, Pages 4203-4206

  Miller, Glen P ^a   Briggs, Jonathan ^a  

^a University of New Hampshire   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FULLERENE DERIVATIVE; PHENYL GROUP;

ARTICLE; DIASTEREOISOMER; STEREOCHEMISTRY; SYNTHESIS;

EID: 0344944879     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0356791     Document Type: Article

References (29)

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28. 3) σ 52.16, 55.09, 72.12, 72.47, 125.55, 127.24, 127.58, 128.20, 128.42, 128.70, 129.19, 129.90, 136.20, 136.59, 136.72, 136.86, 138.82, 138.84, 139.57, 139.79, 139.83, 141.35, 141.48, 141.57, 141.81, 141.82, 141.85, 141.88, 141.94, 142.32, 142.35, 142.40, 142.41, 142.44, 142.48, 142.54, 142.76, 144.42, 144.46, 144.50, 145.06, 145.10, 145.12, 145.18, 145.22, 145.44, 145.45, 145.95, 145.98, 146.00, 146.22, 146.26, 146.27, 147.30, 147.32, 154.96, 155.46.
29. MM2 calculations correctly predict that cis-bis[60]fullerene adduct 1 is preferred to the corresponding trans isomer. Moreover, the 3.08 Å (atoms of closest contact) and 9.84 Å (fullerene centroid-to-centroid) distances between adjacent [60]fullerenes predicted by MM2 are remarkably close to the 3.065 and 9.805 Å distances observed in the X-ray structure of 1. AM1 and PM3 calculations place the atoms of closest contact on adjacent [60]fullerenes ∼4.2 Å apart and the fullerene centroid-to-centroid distance at ∼10.9 Å. See ref 3 for more details.