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Title: Non-pyrolytic syntheses of buckybowls: Corannulene, cyclopentacorannulene, and a semibuckminsterfullerene

Abstract

Corannulene, cyclopentacorannulene, and a C{sub 30}H{sub 12} semibuckminsterfullerene have been prepared by non-pyrolytic methods employing bromomethyl/dibromomethyl and/or dibromomethyl/dibromomethyl coupling with low-valent titanium or vanadium. Reductive coupling of tetrakis(dibromomethyl)-fluoranthene with vanadium(III) chloride and lithium aluminum hydride affords corannulene in 70--75% yield. Similarly, hexakis(dibromomethyl)fluoranthene leads to cyclopentacorannulene in 20--30% yield, and dodecabromo(octamethyl)indenofluoranthene affords semibuckminsterfullerene in 20% yield.

Authors:
;
Publication Date:
Research Org.:
Louisiana State Univ., Baton Rouge, LA (US)
OSTI Identifier:
20000030
Resource Type:
Journal Article
Journal Name:
Journal of the American Chemical Society
Additional Journal Information:
Journal Volume: 121; Journal Issue: 34; Other Information: PBD: 1 Sep 1999; Journal ID: ISSN 0002-7863
Country of Publication:
United States
Language:
English
Subject:
36 MATERIALS SCIENCE; FULLERENES; POLYCYCLIC AROMATIC HYDROCARBONS; SYNTHESIS; CHEMICAL REACTION YIELD; VANADIUM CHLORIDES; REDUCING AGENTS

Citation Formats

Sygula, A., and Rabideau, P.W. Non-pyrolytic syntheses of buckybowls: Corannulene, cyclopentacorannulene, and a semibuckminsterfullerene. United States: N. p., 1999. Web. doi:10.1021/ja991169j.
Sygula, A., & Rabideau, P.W. Non-pyrolytic syntheses of buckybowls: Corannulene, cyclopentacorannulene, and a semibuckminsterfullerene. United States. doi:10.1021/ja991169j.
Sygula, A., and Rabideau, P.W. Wed . "Non-pyrolytic syntheses of buckybowls: Corannulene, cyclopentacorannulene, and a semibuckminsterfullerene". United States. doi:10.1021/ja991169j.
@article{osti_20000030,
title = {Non-pyrolytic syntheses of buckybowls: Corannulene, cyclopentacorannulene, and a semibuckminsterfullerene},
author = {Sygula, A. and Rabideau, P.W.},
abstractNote = {Corannulene, cyclopentacorannulene, and a C{sub 30}H{sub 12} semibuckminsterfullerene have been prepared by non-pyrolytic methods employing bromomethyl/dibromomethyl and/or dibromomethyl/dibromomethyl coupling with low-valent titanium or vanadium. Reductive coupling of tetrakis(dibromomethyl)-fluoranthene with vanadium(III) chloride and lithium aluminum hydride affords corannulene in 70--75% yield. Similarly, hexakis(dibromomethyl)fluoranthene leads to cyclopentacorannulene in 20--30% yield, and dodecabromo(octamethyl)indenofluoranthene affords semibuckminsterfullerene in 20% yield.},
doi = {10.1021/ja991169j},
journal = {Journal of the American Chemical Society},
issn = {0002-7863},
number = 34,
volume = 121,
place = {United States},
year = {1999},
month = {9}
}