Abstract
The dimerization of two triquinacene hemispheres to give dodecahedrane is the holy grail of cycloaddition chemistry. Despite the substantial effort which has been invested in achieving this reaction over the years, no cycloaddition product has been reported. The reason for this failure is that the required endo-endo reactive configuration, involving six double bonds in an S6 symmetrical relationship, is difficult to achieve. In this preliminary report, the self-organization of a triquinacene-based amphiphile at the air-water interface is studied by the surface-sensitive vibrational sum frequency generation technique. The results indicate that the triquinacene bowl is directed into the aqueous subphase, which suggests dimerization of triquinacene may be possible in an aqueous monolayer.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 72-75 |
| Number of pages | 4 |
| Journal | Chemical Physics Letters |
| Volume | 427 |
| Issue number | 1-3 |
| DOIs | |
| State | Published - Aug 18 2006 |
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ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Spectroscopy
- Atomic and Molecular Physics, and Optics
- Surfaces and Interfaces
- Condensed Matter Physics
Cite this
Surface alignment of the N-octadecylazatriquinacenium cation as determined by sum frequency generation on the surface of H2O and D2O. / Baldelli, Steven; Mascal, Mark; Bertran, Jordi Cerón.
In: Chemical Physics Letters, Vol. 427, No. 1-3, 18.08.2006, p. 72-75.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Surface alignment of the N-octadecylazatriquinacenium cation as determined by sum frequency generation on the surface of H2O and D2O
AU - Baldelli, Steven
AU - Mascal, Mark
AU - Bertran, Jordi Cerón
PY - 2006/8/18
Y1 - 2006/8/18
N2 - The dimerization of two triquinacene hemispheres to give dodecahedrane is the holy grail of cycloaddition chemistry. Despite the substantial effort which has been invested in achieving this reaction over the years, no cycloaddition product has been reported. The reason for this failure is that the required endo-endo reactive configuration, involving six double bonds in an S6 symmetrical relationship, is difficult to achieve. In this preliminary report, the self-organization of a triquinacene-based amphiphile at the air-water interface is studied by the surface-sensitive vibrational sum frequency generation technique. The results indicate that the triquinacene bowl is directed into the aqueous subphase, which suggests dimerization of triquinacene may be possible in an aqueous monolayer.
AB - The dimerization of two triquinacene hemispheres to give dodecahedrane is the holy grail of cycloaddition chemistry. Despite the substantial effort which has been invested in achieving this reaction over the years, no cycloaddition product has been reported. The reason for this failure is that the required endo-endo reactive configuration, involving six double bonds in an S6 symmetrical relationship, is difficult to achieve. In this preliminary report, the self-organization of a triquinacene-based amphiphile at the air-water interface is studied by the surface-sensitive vibrational sum frequency generation technique. The results indicate that the triquinacene bowl is directed into the aqueous subphase, which suggests dimerization of triquinacene may be possible in an aqueous monolayer.
UR - http://www.scopus.com/inward/record.url?scp=33746353428&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=33746353428&partnerID=8YFLogxK
U2 - 10.1016/j.cplett.2006.06.038
DO - 10.1016/j.cplett.2006.06.038
M3 - Article
AN - SCOPUS:33746353428
VL - 427
SP - 72
EP - 75
JO - Chemical Physics Letters
JF - Chemical Physics Letters
SN - 0009-2614
IS - 1-3
ER -