Abstract

A facile and efficient synthesis of a new series of triptycene-based tripods is being reported. Using 2,6,14- or 2,7,14-triaminotriptycenes as synthons, the corresponding triazidotriptycenes were prepared in high yield. Additionally, we report the transformation of 2,6,14- or 2,7,14-triaminotriptycenes to the corresponding ethynyl-substituted triptycenes via their tribromo derivatives. Subsequently, derivatization of ethynyl-substituted triptycenes was studied to yield the respective propiolic acid and ethynylphosphine derivatives. Characterization of the newly functionalized triptycene derivatives and their regioisomers were carried out using FTIR and multinuclear NMR spectroscopy, mass spectrometry, and elemental analyses techniques. The study of the interaction of these trisubstituted triptycenes with various forms of DNA revealed interesting dependency on the functional groups of the triptycene core to initiate damage or conformational changes in DNA.

Highlights

  • Triptycene is the simplest member of the class of compounds called iptycenes

  • We describe the syntheses of 2,6,14- and 2,7,14-triptycenetripropiolic acid and tris(ethynyldiphenylphosphino)triptycene derivatives via functional group transformation of triethynyltriptycenes

  • The various functionalized triptycene derivatives have been characterized by FTIR, multinuclear NMR, mass spectrometry and elemental analyses

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Summary

Introduction

Triptycene is the simplest member of the class of compounds called iptycenes. Structurally, iptycenes have a number of arene rings joined together to form the bridges of [2.2.2]bicyclic ring systems. We describe the syntheses of 2,6,14- and 2,7,14-triptycenetripropiolic acid and tris(ethynyldiphenylphosphino)triptycene derivatives via functional group transformation of triethynyltriptycenes.

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