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Title: Precursors to endohedral metal fullerene complexes: Synthesis and X-ray structure of a flexible acetylenic cyclophane C{sub 60}H{sub 18}

Abstract

The rational synthesis of stable endohedral metal fullerene complexes poses a major challenge to current synthetic methodologies. We are particularly interested in C{sub 60} endohedral complexes because C{sub 60} itself has delivered the most interesting physical properties among the empty fullerenes. We are reporting the synthesis, X-ray structure, and preliminary mass spectroscopic study of cyclophane 7 in our first approach to the rational synthesis of fullerenes. An important question to answer is whether the cyclophane 7 can be induced to rearrange to C{sub 60} in the gas phase. MALDI-FTMS and APCI negative ion mass spectrometric studies on 7 have revealed a cluster of peaks around the molecular ion C{sub 60}H{sub 18} at m/z 738. The most abundant ion corresponds to the parent ion 7, with the higher m/z peaks in the approximate relative abundance expected for natural {sub 13}C incorporation in C{sub 60}H{sub 18} and subsequent dehydrogenated species. The lower mass peaks from m/z 734 to 737 indicate that 7 undergoes dehydrogenation at least down to C{sub 60}H{sub 14}; however, no peak for C{sub 60} was detected in the experimental conditions examined so far. 19 refs., 3 figs., 1 tab.

Authors:
; ;  [1]; ;  [2]
  1. Univ. of California, Los Angeles, CA (United States)
  2. Naval Research Lab., Washington, DC (United States)
Publication Date:
OSTI Identifier:
263139
Resource Type:
Journal Article
Journal Name:
Journal of the American Chemical Society
Additional Journal Information:
Journal Volume: 118; Journal Issue: 22; Other Information: PBD: 5 Jun 1996
Country of Publication:
United States
Language:
English
Subject:
36 MATERIALS SCIENCE; 40 CHEMISTRY; FULLERENES; SYNTHESIS; HYDROCARBONS; X-RAY DIFFRACTION; MASS SPECTRA; CRYSTALLIZATION; CRYSTAL STRUCTURE

Citation Formats

Rubin, Y, Parker, T C, Khan, S I, Holliman, C L, and McElvany, S W. Precursors to endohedral metal fullerene complexes: Synthesis and X-ray structure of a flexible acetylenic cyclophane C{sub 60}H{sub 18}. United States: N. p., 1996. Web. doi:10.1021/ja9606384.
Rubin, Y, Parker, T C, Khan, S I, Holliman, C L, & McElvany, S W. Precursors to endohedral metal fullerene complexes: Synthesis and X-ray structure of a flexible acetylenic cyclophane C{sub 60}H{sub 18}. United States. doi:10.1021/ja9606384.
Rubin, Y, Parker, T C, Khan, S I, Holliman, C L, and McElvany, S W. Wed . "Precursors to endohedral metal fullerene complexes: Synthesis and X-ray structure of a flexible acetylenic cyclophane C{sub 60}H{sub 18}". United States. doi:10.1021/ja9606384.
@article{osti_263139,
title = {Precursors to endohedral metal fullerene complexes: Synthesis and X-ray structure of a flexible acetylenic cyclophane C{sub 60}H{sub 18}},
author = {Rubin, Y and Parker, T C and Khan, S I and Holliman, C L and McElvany, S W},
abstractNote = {The rational synthesis of stable endohedral metal fullerene complexes poses a major challenge to current synthetic methodologies. We are particularly interested in C{sub 60} endohedral complexes because C{sub 60} itself has delivered the most interesting physical properties among the empty fullerenes. We are reporting the synthesis, X-ray structure, and preliminary mass spectroscopic study of cyclophane 7 in our first approach to the rational synthesis of fullerenes. An important question to answer is whether the cyclophane 7 can be induced to rearrange to C{sub 60} in the gas phase. MALDI-FTMS and APCI negative ion mass spectrometric studies on 7 have revealed a cluster of peaks around the molecular ion C{sub 60}H{sub 18} at m/z 738. The most abundant ion corresponds to the parent ion 7, with the higher m/z peaks in the approximate relative abundance expected for natural {sub 13}C incorporation in C{sub 60}H{sub 18} and subsequent dehydrogenated species. The lower mass peaks from m/z 734 to 737 indicate that 7 undergoes dehydrogenation at least down to C{sub 60}H{sub 14}; however, no peak for C{sub 60} was detected in the experimental conditions examined so far. 19 refs., 3 figs., 1 tab.},
doi = {10.1021/ja9606384},
journal = {Journal of the American Chemical Society},
number = 22,
volume = 118,
place = {United States},
year = {1996},
month = {6}
}