Exploitation of the majority rules effect for the accurate measurement of high enantiomeric excess values using CD spectroscopy

Seifert, Helen M.; Jiang, Yun Bao; Anslyn, Eric V.

doi:10.1039/c4cc07927b

Cited by 32 publications

(24 citation statements)

References 21 publications

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“…Classic examples are the over‐twisting positive, and under‐twisting negative superhelices of DNA, where a “relax” underwound structure facilitates the DNA helix to open up to be read, thus strongly affecting gene expression . This level of sophistication in nature encourages chemists to design and prepare helical superstructures from synthetic molecules with the aim of creating new functional analogues beyond those in nature . Dendrimers are highly symmetric and branched, aesthetically appealing synthetic macromolecules with precise structures, monodisperse molecular weight, and well‐defined shapes and sizes .…”

Section: Introductionmentioning

confidence: 99%

Trismaleimide Dendrimers: Helix‐to‐Superhelix Supramolecular Transition Accompanied by White‐Light Emission

Wang

et al. 2019

Angewandte Chemie

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Reported here are unprecedented fluorescent superhelices composed of primary, supramolecular polymers of the opposite helical twist. A new class of functional dendrimers was synthesized by amino‐ene click reactions, and they demonstrate an alternating OFF/ON fluorescence with generation growth. A peripherally alkyl‐modified dendrimer displays helix‐sense‐selective supramolecular polymerization, which predominantly forms right‐handed (or left‐handed) helical supramolecular polymers in the solution containing chiral solvents. With increasing the concentration, these primary helical supramolecular polymers spontaneously twist around themselves in the opposite direction to form superhelical structures. Atomic force microscopy and circular dichroism measurements were used to directly observe the helix‐to‐superhelix transition occurring with a reversal in the helical direction. Exceptional white‐light emission was observed during superhelix formation.

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Section: Introductionmentioning

confidence: 99%

Trismaleimide Dendrimers: Helix‐to‐Superhelix Supramolecular Transition Accompanied by White‐Light Emission

Wang

et al. 2019

Angewandte Chemie

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“…[5][6][7][8][9][10][11] Various techniques, including high-performance liquid chromatography (HPLC), nuclear magnetic resonance (NMR), UV/vis, circular dichroism (CD) and fluorescence spectroscopy have been applied to the discrimination and analysis of enantiomers. [12][13][14][15] Enantioselective fluorescent sensors are receiving growing research attention as they potentially provide a real time technique to analysis the enantiomeric composition of chiral organic compounds. [16][17][18][19][20][21][22] Although great development of fluorescent sensors has been achieved, enantioselective fluorescent sensors for structurally diverse chiral α-amino acids still remain challenges in this area due to the zwitterionic property of the α-amino acids, which results in their very slight solubility in organic solvents and little interaction with organic fluorophores in water.…”

Section: Introductionmentioning

confidence: 99%

Chiral fluorescence polyethers based on BINOL for enantioselective recognition of phenylalanine anion

Zhao

Ouyang

Zhang

et al. 2016

Polymer

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Series of polyethers with different configurations were synthesized from chiral BINOL and optical epichlorohydrin. The optical behavior of the obtained polyethers is evaluated with specific optical rotation, UV-vis spectroscopy, circular dichroism (CD) and fluorescence spectroscopy. Thermogravimetric analysis (TGA) reveals the polyethers a good thermal stability. The fluorescence responses of the chiral polyethers on chiral phenylalanine anion were investigated. The sensors (S,S)-4 and (R,R)-4 showed high enantioselective fluorescent sensing ability to phenylalanine anion. The value of enantiomeric fluorescence difference ratio (ef) reached to 6.29.

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“…Moreover, 6 exhibited the same Cotton effect signs in response to the chirality of all the common 19 L-amino acids. Therefore, 6 can be used as a reliable and practically useful synthetic receptor for the rapid detection and precise determination of small enantiomeric imbalances in chiral natural and non-natural amino acids [39,53,54].…”

mentioning

confidence: 99%

Helical Polyacetylenes Induced via Noncovalent Chiral Interactions and Their Applications as Chiral Materials

Maeda

Yashima

2017

Topics in Current Chemistry Collections

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Construction of predominantly one-handed helical polyacetylenes with a desired helix sense utilizing noncovalent chiral interactions with nonracemic chiral guest compounds based on a supramolecular approach is described. As with the conventional dynamic helical polymers possessing optically active pendant groups covalently bonded to the polymer chains, this noncovalent helicity induction system can show significant chiral amplification phenomena, in which the chiral information of the nonracemic guests can transfer with high cooperativity through noncovalent bonding interactions to induce an almost single-handed helical conformation in the polymer backbone. An intriguing ''memory effect'' of the induced macromolecular helicity is observed for some polyacetylenes, which means that the helical conformations induced in dynamic helical polyacetylene can be transformed into metastable static ones by tuning their helix-inversion barriers. Potential applications of helical polyacetylenes with controlled helix sense constructed by the ''noncovalent helicity induction and/or memory effect'' as chiral materials are also described.

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Exploitation of the majority rules effect for the accurate measurement of high enantiomeric excess values using CD spectroscopy

Abstract: A new method for lowering the error of CD based methods for measuring high enantiomeric excess values is described, which exploits the majority rules effect exhibited by certain helical polymers. A proof of principle experiment was conducted.

Cited by 32 publications

References 21 publications

Trismaleimide Dendrimers: Helix‐to‐Superhelix Supramolecular Transition Accompanied by White‐Light Emission

Trismaleimide Dendrimers: Helix‐to‐Superhelix Supramolecular Transition Accompanied by White‐Light Emission

Chiral fluorescence polyethers based on BINOL for enantioselective recognition of phenylalanine anion

Helical Polyacetylenes Induced via Noncovalent Chiral Interactions and Their Applications as Chiral Materials

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