Versatile syntheses of hemi-cryptophanes and a metallo-cryptophane from a hexa-functionalized C3v -symmetrical tribenzotriquinacene (TBTQ) derivative.
Chem Asian J
; 10(5): 1150-8, 2015 May.
Article
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| MEDLINE
| ID: mdl-25641945
ABSTRACT
A number of three-fold C3v -symmetrical tribenzotriquinacene (TBTQ) cavitands were synthesized by a "metamorphosis-to-half" strategy, employing six-fold etherification reactions between the hexakis(chloromethyl)-TBTQ intermediate 2 a 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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01-internacional
Base de datos:
MEDLINE
Asunto principal:
Compuestos Organometálicos
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Compuestos Policíclicos
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Hidrocarburos Aromáticos con Puentes
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Éteres Cíclicos
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En
Revista:
Chem Asian J
Año:
2015
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Article