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Synthesis, Structures and Solid State Self-assemblies of Formyl and Acetyl Substituted Triptycenes and Their Derivatives.
MedLine Citation:
PMID:  23030690     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
Starting from triptycene, 2-, (2,6- or 2,7-)di-, and (2,6,14- or 2,7,14-)tri-formyl 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 regioisomers were well characterized by the FT-IR, 1H NMR, 13C 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.
Authors:
Peng-Fei Li; Chuan-Feng Chen
Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2012-10-2
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  -     ISSN:  1520-6904     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2012 Oct 
Date Detail:
Created Date:  2012-10-3     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
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