Ion-Regulated Allosteric Binding of Fullerenes (C-60 and C-70) by Tetrathiafulvalene-Calix[4]pyrroles
- Authors
- Davis, Christina M.; Lim, Jong Min; Larsen, Karina R.; Kim, Dong Sub; Sung, Young Mo; Lyons, Dani M.; Lynch, Vincent M.; Nielsen, Kent A.; Jeppesen, Jan O.; Kim, Dongho; Park, Jung Su; Sessler, Jonathan L.
- Issue Date
- Jul-2014
- Publisher
- AMER CHEMICAL SOC
- Citation
- JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, v.136, no.29, pp 10410 - 10417
- Pages
- 8
- Journal Title
- JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
- Volume
- 136
- Number
- 29
- Start Page
- 10410
- End Page
- 10417
- URI
- https://scholarworks.sookmyung.ac.kr/handle/2020.sw.sookmyung/10847
- DOI
- 10.1021/ja504077f
- ISSN
- 0002-7863
1520-5126
- Abstract
- The effect of ionic species on the binding of fullerenes (C-60 and C-70) by tetrathiafulvalene-calix[4]pyrrole (TTF-C4P) receptors and the nature of the resulting supramolecular complexes (TTF-C4P + fullerene + halide anion + tetraalkylammonium cation) was studied in the solid state through single crystal X-ray diffraction methods and in dichloromethane solution by means of continuous variation plots and UV-vis spectroscopic titrations. These analyses revealed a 1:1 stoichiometry between the anion-bound TTF-C4Ps and the complexed ftillerenes. The latter guests are bound within the bowl-like cup of the C4P in a ball-and-socket binding mode. The interactions between the TTF-C4P receptors and the fullerene guests are highly influenced by both the nature of halide anions and their counter tetraalkylammonium cations. Three halides (F-, Cl-, and Br-) were studied. All three potentiate the binding of the two test fullerenes by inducing a conformational change from the 1,3-alternate to the cone conformer of the TTF-C4Ps, thus acting as positive heterotropic allosteric effectors. For a particular halide anion, the choice of tetraalkylammonium salts serves to modulate the strength of the TTF-C4P-fullerene host guest binding interactions and, in conjunction with variations in the halide anion, can be exploited to alter the inherent selectivity of the host for a given fullerene. Differences in binding are reflected in the excited state optical properties. Overall, the present four-component system provides an illustration of how host guest binding events involving appropriately designed artificial receptors can be fine-tuned via the addition of simple ionic species as aflosteric modulators.
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