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Preparation of Tri‐ and Hexasubstituted Triptycene Synthons by Transition Metal Catalyzed Cross‐Coupling Reactions for Post‐Modifications
Author(s) -
Moylan Claire,
Rogers Luke,
Shaker Yasser M.,
Davis Mia,
Eckhardt HansGeorg,
Eckert Raphael,
Ryan Aoife A.,
Senge Mathias O.
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201501272
Subject(s) - triptycene , sonogashira coupling , synthon , chemistry , palladium , combinatorial chemistry , coupling reaction , nanotechnology , catalysis , polymer chemistry , stereochemistry , organic chemistry , materials science
Rational building strategies and appropriate synthons have been developed for the use of triptycene as a rigid presenting scaffold. Palladium‐catalyzed cross‐coupling reactions, such as Sonogashira and Suzuki couplings, were used to install a variety of different synthetic handles around the triptycene periphery in a high‐yielding and controlled manner. These triptycene molecular handles were investigated for their potential in the construction of molecular arrays with defined spatial orientation e.g., for host‐guest interactions or drug delivery systems. Such molecular synthons afforded expansion from the triptycene core by employing arm extension to increase the internal free volume characteristic of triptycene scaffolds for such applications. In addition, a range of mesogenic and glycosyl triptycene derivatives were achieved as a synthetic proof of concept for future work on potential drug delivery systems.