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Synthesis of thiophene-capped [2]rotaxanes
Authors:Taichi Ikeda  Masayoshi Higuchi
Affiliation:a Functional Materials Chemistry Group, Organic Nanomaterials Center, National Institute for Materials Science, 1-1 Namiki, Tsukuba 305-0044, Japan
b Experimental Physics, Max Planck Institute for Polymer Research, Ackermannweg 10 Mainz D-55128, Germany
c International Center for Materials Nanoarchitectonics, National Institute for Materials Science, Tsukuba 305-0044, Japan
Abstract:Two types of thiophene-capped [2]rotaxanes, i.e., bithienyl (2T)- and bis(3,4-ethylenedioxythiophene)-yl (BEDOT)-capped [2]rotaxanes, were synthesized. The electron-deficient cyclophane of cyclobis(paraquat-p-phenylene) (CBPQT4+) was used as a macrocycle. Association constants for inclusion complexation of 2T- and BEDOT-derivatives with CBPQT4+ were obtained by 1H NMR titration. Due to the donor-acceptor charge transfer absorption band, 2T- and BEDOT-capped [2]rotaxanes have red and green colors, respectively. On the basis of electrochemical analysis, we confirmed that only BEDOT-capped [2]rotaxane is a promising candidate for [3]rotaxane synthesis through oxidation coupling of the thiophene unit.
Keywords:Rotaxanes   Thiophenes   Charge transfer complex   Electrochemistry
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