CrossRef enabled

PAC Archives

Archive →

Pure Appl. Chem., 2012, Vol. 84, No. 4, pp. 893-905

Published online 2012-01-26

Solution-phase synthesis of bowl- and basket‑shaped fullerene fragments via benzannulated enyne–allenes

Bo Wen and Kung K. Wang

C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, WV 26506-6045, USA

Abstract: Benzannulated enyne-allenes bearing an aryl substituent at both the alkynyl and allenyl termini are excellent precursors of 5-aryl-11H-benzo[b]fluorenyl derivatives having the carbon frameworks of fullerene fragments. The mildness of the reaction conditions and the availability of several synthetic methods for benzannulated enyne-allenes allow the design of new synthetic pathways leading to bowl- and basket-shaped fullerene fragments. Specifically, a bowl-shaped C28H18 hydrocarbon bearing a 27-carbon framework of C60 and a basket-shaped C56H40 hydrocarbon bearing a 54-carbon framework of C60 were synthesized. The interior 30-carbon core of the C56H40 hydrocarbon can be regarded as a partially hydrogenated [5,5]circulene, a C30H12 semibuckminsterfullerene. In addition, a basket-shaped C56H38 hydrocarbon was also constructed to serve as a precursor toward an end-cap template for (6,6) carbon nanotubes.