| SHE, Nengfang, Damien MONCELET, Laura GILBERG, Xiaoyong LU, Vladimír ŠINDELÁŘ, Volker BRIKEN and Lyle ISAACS. Glycoluril-Derived Molecular Clips are Potent and Selective Receptors for Cationic Dyes in Water. Chemistry - A European Journal. WEINHEIM: Wiley, 2016, vol. 22, No 43, p. 15270-15279. ISSN 0947-6539. Available from: https://dx.doi.org/10.1002/chem.201601796. |
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@article{1369947,
author = {She, Nengfang and Moncelet, Damien and Gilberg, Laura and Lu, Xiaoyong and Šindelář, Vladimír and Briken, Volker and Isaacs, Lyle},
article_location = {WEINHEIM},
article_number = {43},
doi = {http://dx.doi.org/10.1002/chem.201601796},
keywords = {cation-pi interactions; dyes; glycoluril; hydrophobic effects; molecular clip},
language = {eng},
issn = {0947-6539},
journal = {Chemistry - A European Journal},
title = {Glycoluril-Derived Molecular Clips are Potent and Selective Receptors for Cationic Dyes in Water},
volume = {22},
year = {2016}
}
TY - JOUR
ID - 1369947
AU - She, Nengfang - Moncelet, Damien - Gilberg, Laura - Lu, Xiaoyong - Šindelář, Vladimír - Briken, Volker - Isaacs, Lyle
PY - 2016
TI - Glycoluril-Derived Molecular Clips are Potent and Selective Receptors for Cationic Dyes in Water
JF - Chemistry - A European Journal
VL - 22
IS - 43
SP - 15270-15279
EP - 15270-15279
PB - Wiley
SN - 09476539
KW - cation-pi interactions
KW - dyes
KW - glycoluril
KW - hydrophobic effects
KW - molecular clip
N2 - Molecular clip 1 remains monomeric in water and engages in host-guest recognition processes with suitable guests. We report the K-a values for 32 1.guest complexes measured by H-1 NMR, UV/Vis, and fluorescence titrations. The cavity of 1 is shaped by aromatic surfaces of negative electrostatic potential and therefore displays high affinity and selectivity for planar and cationic aromatic guests that distinguishes it from CB[n] receptors that prefer aliphatic over aromatic guests. Electrostatic effects play a dominant role in the recognition process whereby ion-dipole interactions may occur between ammonium ions and the C=O groups of 1, between the SO3- groups of 1 and pendant cationic groups on the guest, and within the cavity of 1 by cation-pi interactions. Host 1 displays a high affinity toward dicationic guests with large planar aromatic surfaces (e.g. naphthalene diimide NDI + and perylene diimide PDI +) and cationic dyes derived from acridine (e.g. methylene blue and azure A). The critical importance of cation-pi interactions was ascertained by a comparison of analogous neutral and cationic guests (e.g. methylene violet vs. methylene blue; quinoline vs. N-methylquinolinium; acridine vs. N-methylacridinium; neutral red vs. neutral red H+) the affinities of which differ by up to 380-fold. We demonstrate that the high affinity of 1 toward methylene blue (K-a = 3.92 x 10(7) M-1; K-d = 25 nm) allows for the selective sequestration and destaining of U87 cells stained with methylene blue.
ER -
SHE, Nengfang, Damien MONCELET, Laura GILBERG, Xiaoyong LU, Vladimír ŠINDELÁŘ, Volker BRIKEN and Lyle ISAACS. Glycoluril-Derived Molecular Clips are Potent and Selective Receptors for Cationic Dyes in Water. \textit{Chemistry - A European Journal}. WEINHEIM: Wiley, 2016, vol.~22, No~43, p.~15270-15279. ISSN~0947-6539. Available from: https://dx.doi.org/10.1002/chem.201601796.
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