Versatile Syntheses of Hemi-Cryptophanes and a Metallo-Cryptophane from a Hexa-Functionalized C-3v-Symmetrical Tribenzotriquinacene (TBTQ) Derivative

Wei J, Li Z-M, Jin X-J, Yao X-J, Cao X-P, Chow H-F, Kuck D (2015)
Chemistry - An Asian Journal 10(5): 1150-1158.

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Abstract
A number of three-fold C-3v-symmetrical tribenzotriquinacene (TBTQ) cavitands were synthesized by a metamorphosis-to-half strategy, employing six-fold etherification reactions between the hexakis(chloromethyl)-TBTQ intermediate 2a and various 5-functionalized resorcinols. X-ray structure analyses of single crystals of the cavitands revealed limited rotational flexibility of the resorcinol bridging units, which enables an apical, nearly co-axial orientation of the three functional groups and, as a consequence, the construction of nanoscale cage-like molecules via covalent or coordination bonding. On this basis, two TBTQ-based hemicryptophanes were prepared from the TBTQ cavitands via covalent bond formation in good yields. A dumbbell-shaped TBTQ-based metallo-cryptophane was also synthesized in 34% yield by a solvothermal reaction between cadmium nitrate and two equivalents of the TBTQ-cavitand triacid, as confirmed by single-crystal X-ray diffraction and MALDI-ToF mass spectrometry.
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Wei J, Li Z-M, Jin X-J, et al. Versatile Syntheses of Hemi-Cryptophanes and a Metallo-Cryptophane from a Hexa-Functionalized C-3v-Symmetrical Tribenzotriquinacene (TBTQ) Derivative. Chemistry - An Asian Journal. 2015;10(5):1150-1158.
Wei, J., Li, Z. - M., Jin, X. - J., Yao, X. - J., Cao, X. - P., Chow, H. - F., & Kuck, D. (2015). Versatile Syntheses of Hemi-Cryptophanes and a Metallo-Cryptophane from a Hexa-Functionalized C-3v-Symmetrical Tribenzotriquinacene (TBTQ) Derivative. Chemistry - An Asian Journal, 10(5), 1150-1158.
Wei, J., Li, Z. - M., Jin, X. - J., Yao, X. - J., Cao, X. - P., Chow, H. - F., and Kuck, D. (2015). Versatile Syntheses of Hemi-Cryptophanes and a Metallo-Cryptophane from a Hexa-Functionalized C-3v-Symmetrical Tribenzotriquinacene (TBTQ) Derivative. Chemistry - An Asian Journal 10, 1150-1158.
Wei, J., et al., 2015. Versatile Syntheses of Hemi-Cryptophanes and a Metallo-Cryptophane from a Hexa-Functionalized C-3v-Symmetrical Tribenzotriquinacene (TBTQ) Derivative. Chemistry - An Asian Journal, 10(5), p 1150-1158.
J. Wei, et al., “Versatile Syntheses of Hemi-Cryptophanes and a Metallo-Cryptophane from a Hexa-Functionalized C-3v-Symmetrical Tribenzotriquinacene (TBTQ) Derivative”, Chemistry - An Asian Journal, vol. 10, 2015, pp. 1150-1158.
Wei, J., Li, Z.-M., Jin, X.-J., Yao, X.-J., Cao, X.-P., Chow, H.-F., Kuck, D.: Versatile Syntheses of Hemi-Cryptophanes and a Metallo-Cryptophane from a Hexa-Functionalized C-3v-Symmetrical Tribenzotriquinacene (TBTQ) Derivative. Chemistry - An Asian Journal. 10, 1150-1158 (2015).
Wei, Jun, Li, Zhi-Min, Jin, Xiao-Jie, Yao, Xiao-Jun, Cao, Xiao-Ping, Chow, Hak-Fun, and Kuck, Dietmar. “Versatile Syntheses of Hemi-Cryptophanes and a Metallo-Cryptophane from a Hexa-Functionalized C-3v-Symmetrical Tribenzotriquinacene (TBTQ) Derivative”. Chemistry - An Asian Journal 10.5 (2015): 1150-1158.
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