Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 77, Issue 20, Pages 9250-9259Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo301820v
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Funding
- National Natural Science Foundation of China [20972162, 91127009]
- Ministry of Science and Technology of China [2011CB932501]
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Starting from triptycene, 2-, (2,6- or 2,7-)di-, and (2,6,14- or 2,7,14-)triformyl or acetyl substituted triptycenes were selectively synthesized. The derivatization of the formyl or acetyl substituted triptycenes was then investigated. Consequently, it was found that the formyl-substituted triptycenes could be transformed into cyano substituted triptycene derivatives by the aldoxime formation and dehydration. Acetoxyl- and acetamino-substituted triptycenes were synthesized by Baeyer-Villiger oxidation of acetyl-substituted triptycenes and Beckmann rearrangement of acetyl-oxime triptycenes, respectively. Deacetylation of triacetaminotriptycene provided an alternative way to the synthesis of triaminotriptycene. In addition, 2-ethynyltriptycene could be conveniently synthesized by Corey-Fuchs reaction of 2-formyltriptycene, and 1,3,5-tritriptycenebenzene was obtained in high yield by the dehydration cyclotrimerization of 2-acetyltriptycene. The different functionalized triptycene derivatives and their regioisoniers were well characterized by the FT-IR, H-1 NMR, C-13 NMR, MS spectra, and single crystal X-ray analyses. Moreover, it was also found that 2,6,14-triacetaminotriptycene with the three amide groups paralleled to their connected aromatic rings could self-assemble into a 2D layer with porous structure, and further 3D microporous architecture by the hydrogen-bond network in the solid state.
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