Synthesis and Characterization of Natural Abundance and Isotopically Labeled 1,4-Bis(3,3,3-triphenylpropynyl)-2,3-difluorobenzene. A Molecular Gyroscope with a Polar Rotator
DOI:
https://doi.org/10.29356/jmcs.v52i2.1058Keywords:
molecular machines, molecular rotors, isotopic substitution, X-ray structureAbstract
Sonogashira coupling of natural abundance and d2-deuterated 1,4-bis(trifluoromethanesulfonate)-2,3-difluorobenzene provides access to 1,4-bis(3,3,3-triphenylpropynyl)-2,3-difluorobenzene, a structure that emulates a molecular gyroscope with a dipolar rotator. Two crystal forms of this compound are of interest for the construction of ferroelectric materials.
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References
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2. (a) Karlen, S. D.; Garcia-Garibay, M. A. Topics Curr. Chem. 2006, 262, 179-228. (b) Khuong, T.-A. V.; Nuñez, J. E.; Godinez, C. E.; Garcia-Garibay, M. A., Acc. Chem. Res. 2006, 39, 413-422.
3. (a) Dominguez, Z.; Dang, H.; Strouse, M.J.; Garcia-Garibay, M.A. J. Am. Chem. Soc., 2002, 124, 2398-2399. (b) Dominguez, Z.; Dang, H.; Strouse, J. M.; Garcia-Garibay, M. A. J. Am. Chem. Soc., 2002, 124, 7719-7727.
4. Kottas, G. S.; Clarke, L. I.; Horinek, D.; Michl, J. Chem. Rev. 2005, 105, 1281.
5. Dominguez, Z.; Khuong, T.A.V.; Sanrame, Dang, H.; Garcia-Garibay, M. A. J. Am. Chem. Soc., 2003 125, 8827-8837.
6. Horansky, R. D.; Clarke, L. I.; Winston, E. B.; Price, J. C.; Karlen, S. D.; Jarowski, P. D.; Santillan, R.; Garcia-Garibay, M.A. Phys. Rev. B., 2006, 74, 054306.
7. A clathrate is a stoichiometric two-component crystalline structure which, unlike an inclusion compound, can only exist as such in the solid state. Compound 1 is structurally related to molecules known as wheel-and-axle clathrates. For leading references please see: McNicol, D. D.; Toda, F.; Bishop, R. Comprehensive Supramolecular Chemistry; Pergamon: Oxford, 1996; Vol. 6.
8. (a) Scudder, M.; Dance, I. J. Chem. Soc., Dalton Trans. 1998, 329-344. (b) Scudder, M.; Dance, I. Dalton 2000, 2909-2915. (c) Dance, I.; Scudder, M. New Journal of Chemistry 1998, 22, 481-492. (d) Lacour, J.; Bernardinelli, G.; Russell, V.; Dance, I. CrystEngComm 2002, 4, 165-170. (e) Karlen, S. D: Kahn, S. I.; Garcia-Garibay, M.A. Cryst. Growth & Design, 2005, 5, 53-55.
9. Essers, M.; Haufe, G. J. Chem. Soc., Perkin Trans. 1, 2002, 2719-2728.
10. Stang, Peter J.; Hanack, Michael; Subramanian, L. R. Synthesis 1982, 85-126.
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2019-07-31
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