World Journal of Organic Chemistry
ISSN (Print): 2372-2150 ISSN (Online): 2372-2169 Website: http://www.sciepub.com/journal/wjoc Editor-in-chief: Subrata Shaw
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World Journal of Organic Chemistry. 2021, 9(1), 1-5
DOI: 10.12691/wjoc-9-1-1
Open AccessArticle

Trisubstituted Triptycenes: Toward the Preparation of Three-Dimensional Dendrimers

Alfredo Mellace1 and James E. Hanson1,

1Department of Chemistry and Biochemistry, Seton Hall University, South Orange, New Jersey, USA

Pub. Date: May 27, 2021

Cite this paper:
Alfredo Mellace and James E. Hanson. Trisubstituted Triptycenes: Toward the Preparation of Three-Dimensional Dendrimers. World Journal of Organic Chemistry. 2021; 9(1):1-5. doi: 10.12691/wjoc-9-1-1

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

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