Article
Trisubstituted Triptycenes: Toward the Preparation of Three-Dimensional Dendrimers
World Journal of Organic Chemistry
(2021)
Abstract
A synthesis of benzyl trisubstituted triptycenes is described. These triptycenes are precursors for producing a first generation (G1) poly(triptycylether) dendrimer, a derivative of known poly(arylether) dendrimers. The molecule necessary for the further elaboration into the eventual dendrimer is a carboxylic acid ester triptycene terminated with two ether substituents on another ring; the zero generation (G0). The synthesis begins with formation of the Diels-Alder adduct of benzoquinone and methyl 2-anthroate. This adduct is aromatized under basic conditions and the resulting anion trapped with a benzyl halide as an electrophile to form the trisubstituted triptycene. Access to the trisubstituted system is obtained through a highly improved, efficient and chromatography free preparation of anthracene derivatives, mainly methyl 2-anthroate.
Keywords
- triptycenes,
- dendrimers,
- monodendrons
Disciplines
Publication Date
May, 2021
DOI
10.12691/wjoc-9-1-1
Citation Information
Alfredo Mellace and James E Hanson. "Trisubstituted Triptycenes: Toward the Preparation of Three-Dimensional Dendrimers" World Journal of Organic Chemistry Vol. 9 Iss. 1 (2021) p. 1 - 5 ISSN: 2372-2169 Available at: http://works.bepress.com/dr_james_hanson/26/