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Wiehe, A.; Senge, M.O.; Schafer, A.; Seck, M.; Tannert, S.; Kurreck, H.; Roder, B. “Electron Donor-Acceptor Compounds: exploiting the triptycene geometry for the synthesis of porphyrin quinone diads, triads and a tetrad” Tetrahedron, 57, 10089-10110, 2001.

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Article

Trisubstituted Triptycenes: Toward the Preparation of Three-Dimensional Dendrimers

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


World Journal of Organic Chemistry. 2021, Vol. 9 No. 1, 1-5
DOI: 10.12691/wjoc-9-1-1
Copyright © 2021 Science and Education Publishing

Cite this paper:
Alfredo Mellace, 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.

Correspondence to: James  E. Hanson, Department of Chemistry and Biochemistry, Seton Hall University, South Orange, New Jersey, USA. Email: james.hanson@shu.edu

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.

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