Quantum Mechanical and Experimental Validation that Cyclobis(paraquat-p-phenylene) Forms a 1:1 Inclusion Complex with Tetrathiafulvalene

Chemistry : a European Journal
Karel J HartliebJ Fraser Stoddart

Abstract

The promiscuous encapsulation of π-electron-rich guests by the π-electron-deficient host, cyclobis(paraquat-p-phenylene) (CBPQT(4+) ), involves the formation of 1:1 inclusion complexes. One of the most intensely investigated charge-transfer (CT) bands, assumed to result from inclusion of a guest molecule inside the cavity of CBPQT(4+) , is an emerald-green band associated with the complexation of tetrathiafulvalene (TTF) and its derivatives. This interpretation was called into question recently in this journal based on theoretical gas-phase calculations that reinterpreted this CT band in terms of an intermolecular side-on interaction of TTF with one of the bipyridinium (BIPY(2+) ) units of CBPQT(4+) , rather than the encapsulation of TTF inside the cavity of CBPQT(4+) . We carried out DFT calculations, including solvation, that reveal conclusively that the CT band emerging upon mixing TTF with CBPQT(4+) arises from the formation of a 1:1 inclusion complex. In support of this conclusion, we have performed additional experiments on a [2]rotaxane in which a TTF unit, located in the middle of its short dumbbell, is prevented sterically from interacting with either one of the two BIPY(2+) units of a CBPQT(4+) ring residing on a sepa...Continue Reading

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Citations

Jun 7, 2016·Journal of the American Chemical Society·Chuyang ChengJ Fraser Stoddart
Feb 13, 2020·Chemistry : a European Journal·Morten JensenJan Oskar Jeppesen
Mar 11, 2021·Organic Letters·Takaaki MoriseYuji Tokunaga

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