Point-to-Axial Chirality Transfer—A New Probe for “Sensing” the Absolute Configurations of Monoamines

Anyika, Mercy; Gholami, Hadi; Ashtekar, Kumar Dilip; Acho, Robert; Borhan, Babak

doi:10.1021/ja408317b

Cited by 102 publications

(74 citation statements)

References 76 publications

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“…The same principles have been exploited for the assignment of the absolute configuration of chiral carboxylic acids using a biphenyl‐derived azepine probe . Borhan and colleagues recently proposed an elegant chiroptical sensor for the detection of monofunctional amines . The working principle makes use of the exciton coupled circular dichroism (ECCD) protocol, which allows, essentially on the basis of the shape of signal, with the support of calculations, the assignment of the stereochemical configuration based on the observed Cotton effects.…”

Section: Resultsmentioning

confidence: 99%

Recent Advances in Sensing Using Atropoisomeric Molecular Receptors

Pasini

Nitti

2015

Chirality

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We describe recent advances in chiroptical chemical sensors, in which the design and implementation is based upon the introduction of atropoisomerically chiral moiety within the molecular skeleton. This report include examples of acyclic, macrocyclic, and polymeric receptors that contain this motif. Although the main applications are in the enantioselective sensing of analytes, we report here some cases where the chiral receptors can in fact be used to senseachiral species. Using circular dichroism (CD) spectroscopy as the technique to detect a receptor-analyte interaction, we can distinguish two main sensor categories: that in which the CD signal of a stereolabile, CD-silent probe is activated upon binding, and that in which the signal of a CD-active probe is modulated upon binding. Particular emphasis will be given to cases in which CD spectroscopy is used orthogonally to other means of detection.

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Section: Resultsmentioning

confidence: 99%

Recent Advances in Sensing Using Atropoisomeric Molecular Receptors

Pasini

Nitti

2015

Chirality

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“…[3] As the zinc porphyrin readily binds to amine groups these tweezers can be very useful to determine the absolute stereochemistry of a variety of natural and synthesised diamines. [11][12][13][14] In most cases where molecules with only one binding site are studied derivatization is used to facilitate ditopic binding by providing a second binding site. Thus, bisporphyrin tweezers have been successively used on diols, amino alcohols amino acids and carboxylic acids.…”

Section: Introductionmentioning

confidence: 99%

Exciton‐Coupled Circular Dichroism Characterization of Monotopically Binding Guests in Host−Guest Complexes with a Bis(zinc porphyrin) Tweezer

et al. 2018

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A stiff-stilbene-linked bisporphyrin tweezer with inherent helicity was used for exciton-coupled circular dichroism (ECCD) characterization of a series of monotopically binding amine guest molecules. CD signals were observed for a variety of monoamines at relatively low tweezer/amine (host/guest) ratios between 1 : 10 to 1 : 70. For the amines producing the most intense CD signals, a binding stoichiometry of 1 : 2 was found. A likely explanation is the presence of guest-guest interactions in the complexes. This is supported by the correlation observed between CD signal intensity and magnitude of possible noncovalent binding between the guests, which can be divided into three groups showing no, moderate and strong response, respectively. Further support for this rationalization comes from molecular modelling.

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“…[1] In this context, particular attention has been devoted to the determination of enantiomeric excess (ee) by using optical methods. [5][6][7][8] Among the different techniques, electronic circular dichroism is dominant, even though alternative techniques have been extensively studied as well. [5][6][7][8] Among the different techniques, electronic circular dichroism is dominant, even though alternative techniques have been extensively studied as well.…”

Section: Introductionmentioning

confidence: 99%

Second‐Generation Tris(2‐pyridylmethyl)amine–Zinc Complexes as Probes for Enantiomeric Excess Determination of Amino Acids

et al. 2017

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Self‐assembly through imine condensation chemistry in combination with metal coordination is becoming one of the leading strategies for the preparation of stereodynamic probes for the determination of enantiomeric excess. Recently, we reported a novel molecular architecture based on a modified tris(2‐pyridylmethyl)amine–zinc(II) complex [TPMA = tris(2‐pyridylmethyl)amine] that is able to function as an optical probe for the determination of the enantiomeric excess of amino acids. Herein, we report on how a slight modification of the TPMA ligand enhances both the dichroic response and the stability of the system. The novel probe provides a much higher dichroic signal compared with the previously reported system.

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Point-to-Axial Chirality Transfer—A New Probe for “Sensing” the Absolute Configurations of Monoamines

Cited by 102 publications

References 76 publications

Recent Advances in Sensing Using Atropoisomeric Molecular Receptors

Recent Advances in Sensing Using Atropoisomeric Molecular Receptors

Exciton‐Coupled Circular Dichroism Characterization of Monotopically Binding Guests in Host−Guest Complexes with a Bis(zinc porphyrin) Tweezer

Second‐Generation Tris(2‐pyridylmethyl)amine–Zinc Complexes as Probes for Enantiomeric Excess Determination of Amino Acids

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