Recognition of Viologen Derivatives in Water by N-Alkyl Ammonium Resorcinarene Chlorides

Ngong K. Beyeh; Hyun Hwa Jo; Igor Kolesnichenko; Fangfang  Pan; Elina Kalenius; Eric V. Anslyn; Robin H. A. Ras; Kari Rissanen

doi:10.1021/acs.joc.7b00449

Recognition of Viologen Derivatives in Water by N-Alkyl Ammonium Resorcinarene Chlorides

Ngong K. Beyeh, Hyun Hwa Jo, Igor Kolesnichenko, Fangfang Pan, Elina Kalenius, Eric V. Anslyn, Robin H. A. Ras, Kari Rissanen

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Abstract

Three water-soluble N-alkyl ammonium resorcinarene chlorides decorated with terminal hydroxyl groups at the lower rims were synthesized and characterized. The receptors were decorated at the upper rim with either terminal hydroxyl, rigid cyclohexyl, or flexible benzyl groups. The binding affinities of these receptors toward three viologen derivatives, two of which possess an acetylmethyl group attached to one of the pyridine nitrogens, in water were investigated via 1H NMR spectroscopy, fluorescence spectroscopy, and isothermal titration calorimetry (ITC). ITC quantification of the binding process gave association constants of up to 103 M–1. Analyses reveal a spontaneous binding process which are all exothermic and are both enthalpy and entropy driven.

Original language	English
Article number	10
Pages (from-to)	5198–5203
Journal	Journal of Organic Chemistry
Volume	82
Issue number	10
DOIs	https://doi.org/10.1021/acs.joc.7b00449
Publication status	Published - 28 Apr 2017
MoE publication type	A1 Journal article-refereed

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10.1021/acs.joc.7b00449

CCDC 1525503: Experimental Crystal Structure Determination
Anslyn, E. V. (Contributor), Beyeh, N. (Creator), Jo, H. H. (Contributor), Kalenius, E. (Contributor), Kolesnichenko, I. (Contributor), Pan, F. (Contributor), Ras, R. (Creator) & Rissanen, K. (Contributor), Cambridge Crystallographic Data Centre , 1 Jan 2017
DOI: 10.5517/ccdc.csd.cc1n6ds1, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1n6ds1&sid=DataCite
Dataset
CCDC 1525501: Experimental Crystal Structure Determination
Anslyn, E. V. (Creator), Beyeh, N. (Creator), Jo, H. H. (Creator), Kalenius, E. (Creator), Kolesnichenko, I. (Creator), Pan, F. (Creator), Ras, R. (Creator) & Rissanen, K. (Creator), Cambridge Crystallographic Data Centre , 4 Jan 2017
DOI: 10.5517/ccdc.csd.cc1n6dqz, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1n6dqz&sid=DataCite
Dataset
CCDC 1525502: Experimental Crystal Structure Determination
Anslyn, E. V. (Contributor), Beyeh, N. (Creator), Jo, H. H. (Contributor), Kalenius, E. (Contributor), Kolesnichenko, I. (Contributor), Pan, F. (Contributor), Ras, R. (Contributor) & Rissanen, K. (Contributor), Cambridge Crystallographic Data Centre , 1 Jan 2017
DOI: 10.5517/ccdc.csd.cc1n6dr0, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1n6dr0&sid=DataCite
Dataset

Cite this

@article{9720838aa5524f7abecfc81263419da4,

title = "Recognition of Viologen Derivatives in Water by N-Alkyl Ammonium Resorcinarene Chlorides",

abstract = "Three water-soluble N-alkyl ammonium resorcinarene chlorides decorated with terminal hydroxyl groups at the lower rims were synthesized and characterized. The receptors were decorated at the upper rim with either terminal hydroxyl, rigid cyclohexyl, or flexible benzyl groups. The binding affinities of these receptors toward three viologen derivatives, two of which possess an acetylmethyl group attached to one of the pyridine nitrogens, in water were investigated via 1H NMR spectroscopy, fluorescence spectroscopy, and isothermal titration calorimetry (ITC). ITC quantification of the binding process gave association constants of up to 103 M–1. Analyses reveal a spontaneous binding process which are all exothermic and are both enthalpy and entropy driven.",

author = "Beyeh, {Ngong K.} and Jo, {Hyun Hwa} and Igor Kolesnichenko and Fangfang Pan and Elina Kalenius and Anslyn, {Eric V.} and Ras, {Robin H. A.} and Kari Rissanen",

year = "2017",

month = apr,

day = "28",

doi = "10.1021/acs.joc.7b00449",

language = "English",

volume = "82",

pages = "5198–5203",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "10",

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TY - JOUR

T1 - Recognition of Viologen Derivatives in Water by N-Alkyl Ammonium Resorcinarene Chlorides

AU - Beyeh, Ngong K.

AU - Jo, Hyun Hwa

AU - Kolesnichenko, Igor

AU - Pan, Fangfang

AU - Kalenius, Elina

AU - Anslyn, Eric V.

AU - Ras, Robin H. A.

AU - Rissanen, Kari

PY - 2017/4/28

Y1 - 2017/4/28

N2 - Three water-soluble N-alkyl ammonium resorcinarene chlorides decorated with terminal hydroxyl groups at the lower rims were synthesized and characterized. The receptors were decorated at the upper rim with either terminal hydroxyl, rigid cyclohexyl, or flexible benzyl groups. The binding affinities of these receptors toward three viologen derivatives, two of which possess an acetylmethyl group attached to one of the pyridine nitrogens, in water were investigated via 1H NMR spectroscopy, fluorescence spectroscopy, and isothermal titration calorimetry (ITC). ITC quantification of the binding process gave association constants of up to 103 M–1. Analyses reveal a spontaneous binding process which are all exothermic and are both enthalpy and entropy driven.

AB - Three water-soluble N-alkyl ammonium resorcinarene chlorides decorated with terminal hydroxyl groups at the lower rims were synthesized and characterized. The receptors were decorated at the upper rim with either terminal hydroxyl, rigid cyclohexyl, or flexible benzyl groups. The binding affinities of these receptors toward three viologen derivatives, two of which possess an acetylmethyl group attached to one of the pyridine nitrogens, in water were investigated via 1H NMR spectroscopy, fluorescence spectroscopy, and isothermal titration calorimetry (ITC). ITC quantification of the binding process gave association constants of up to 103 M–1. Analyses reveal a spontaneous binding process which are all exothermic and are both enthalpy and entropy driven.

U2 - 10.1021/acs.joc.7b00449

DO - 10.1021/acs.joc.7b00449

M3 - Article

SN - 0022-3263

VL - 82

SP - 5198

EP - 5203

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 10

M1 - 10

ER -

Recognition of Viologen Derivatives in Water by N-Alkyl Ammonium Resorcinarene Chlorides

Abstract

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Datasets

CCDC 1525503: Experimental Crystal Structure Determination

CCDC 1525501: Experimental Crystal Structure Determination

CCDC 1525502: Experimental Crystal Structure Determination

Cite this