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Studies Toward the Synthesis of Phenylacetylene Macrocycle Based Rotaxane Precursors as Building Blocks for Organic Nanotubes
Author(s) -
Cantin Katy,
LafleurLambert Antoine,
Dufour Philippe,
Morin JeanFrançois
Publication year - 2012
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.201200655
Subject(s) - phenylacetylene , rotaxane , sonogashira coupling , chemistry , nanotechnology , combinatorial chemistry , polymer chemistry , molecule , organic chemistry , supramolecular chemistry , materials science , palladium , catalysis
Synthetic efforts toward the preparation of rotaxane precursors based on phenylacetylene macrocycles (PAM) are described. The aim of this study was to determine the optimal structural parameters to prepare high‐molecular‐weight rotaxane precursors through a strategy involving two Sonogashira couplings to attach bulky blockers on the PAM core. PAMs with different sizes and functions were prepared and coupled to different blockers to assess whether or not the resulting structure adopts a rotaxane‐like conformation in which the rigid rod forms after the Sonogashira coupling threads through the PAM.