T. Sasaki, J. M. Tour / Tetrahedron Letters 48 (2007) 5821–5824
5823
Pd(PPh3)2Cl2
CuI, TEA, THF
article can be found, in the online version, at
8 + 14
70%
References and notes
MeO
MeO
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NMe2
OMe
OMe
´
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R = TIPS, 15
R = H, 16
´
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CuI, TEA, THF
6 + 16
31%
MeO
MeO
O2N
NMe2
OMe
OMe
1
Scheme 3. Synthesis of the dipolar nanocar 1.
tion of isatogen byproducts when an aromatic nitro
group is ortho to an alkyne.17
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In summary, we have designed and successfully synthe-
sized a new dipolar nanocar 1. The dipolar nanocar 1
bears a donor–acceptor functionality that should allow
for the enhanced electric-field-induced rolling of the
molecule by an oriented electric field. The STM-based
electron-field-induce rolling experiment and the synthe-
sis of dipolar nanocars with other wheel systems such
as C60 are currently underway.
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Acknowledgments
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4542.
We thank the Welch Foundation, Zyvex Corporation,
American Honda Motor Co., and the NSF Penn State
MRSEC for financial support. The NSF, CHEM
0075728, provided partial funding for the 400 MHz
NMR. We thank Drs. I. Chester of FAR Research,
Inc. and R. Awartari of Petra Research, Inc. for provid-
ing trimethylsilyacetylene.
8. Jian, H.; Tour, J. M. J. Org. Chem. 2003, 68, 5091–
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Supplementary data
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The supplementary data include experimental details as
well as spectroscopic data (melting point, FTIR, 1H
NMR, 13C NMR, mass spectrometry) for compounds
1, 3–8, 10–16. Supplementary data associated with this