A chiral binaphthyl-based coordination polymer as an enantioselective fluorescence sensor

Thoonen, Shannon; Tay, Hui Min; Hua, Carol

doi:10.1039/d1cc06872e

Cited by 17 publications

(21 citation statements)

References 25 publications

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“…CBPPs-OH polymers crushed in a mortar and suspended in MeCN show in their UV–vis spectra absorption maxima at 228, 278 nm (( S )-CBPPSu), 224, 272 nm (( R )-CBPPSo1), and 224, 280 nm (( R )-CBPPSo2) (Figure S5 in ESI). These bands are due to π–π*, as has been reported for other BINOL derivatives . To confirm that the emissions observed are due to the fluorescence phenomena, the same spectra were recorded at λ ex of choice ±10 nm; if the maximum λ em is maintained, we are observing fluorescence emission.…”

Section: Resultssupporting

confidence: 58%

BINOL-Containing Chiral Porous Polymers as Platforms for Enantiorecognition

Valverde‐González

Borrallo-Aniceto

Pintado‐Sierra

et al. 2022

ACS Appl. Mater. Interfaces

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The enantioselective discrimination of racemic compounds can be achieved through the design and preparation of a new family of chiral conjugated BINOL−porous polymers (CBPPs) from enantiopure (R)-or (S)-BINOL derivatives and 1,3,5-tris(4-phenylboronic acid)benzene or 1,3,5-tris(4-ethynylphenyl)benzene, 1,3,5triethynyl-2,4,6-trifluorobenzene, and tetra(4-ethynylphenyl)methane as comonomers following Suzuki−Miyaura and Sonogashira−Hagihara carbon−carbon coupling approaches. The obtained CBPPs show high thermal stability, a good specific surface area, and a robust framework and can be applied successfully in the fluorescence recognition of enantiomers of terpenes (limonene and α-pinene) and 1-phenylethylamine. Fluorescence titration of CBPPs-OH in acetonitrile shows that all Sonogashira hosts exhibit a preference for the (R)-enantiomer over the (S)-enantiomer of 1-phenylethylamine, the selectivity being much higher than that of the corresponding BINOL-based soluble system used as a reference. However, the Suzuki host reveals a preference toward (S)-phenylethylamine. Regarding the sensing of terpenes, only Sonogashira hosts show enantiodifferentiation with an almost total preference for the (S)-enantiomer of limonene and α-pinene. Based on the computational simulations and the experimental data, with 1-phenylethylamine as the analyte, chiral recognition is due to the distinctive binding affinities resulting from N•••H−O hydrogen bonds and the π−π interaction between the host and the guest. However, for limonene, the geometry of the adsorption complex is mostly governed by the interaction between the hydroxyl group of the BINOL unit and the C�C bond of the isopropenyl fragment. The synthetic strategy used to prepare CBPPs opens many possibilities to place chiral centers such as BINOL in porous polymers for different chiral applications such as enantiomer recognition.

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Section: Resultssupporting

confidence: 58%

BINOL-Containing Chiral Porous Polymers as Platforms for Enantiorecognition

Valverde‐González

Borrallo-Aniceto

Pintado‐Sierra

et al. 2022

ACS Appl. Mater. Interfaces

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“…For example, a fluorescent, chiral coordination polymer was synthesized with a novel topology for differential interaction with chiral Mosher's acids to provide a special quenching-based fluorescent signal. 232 Active nanostructures or nanomaterials are also attractive selectors for SERS-based chiral sensing. Compared with other optical techniques, SERS is unique for single-molecule-level sensitivity and information-rich and label-free chiral discrimination.…”

Section: ■ Sensingmentioning

confidence: 99%

“…Special topological structures of these nanomaterials with analytes contribute to the chiral sensing. For example, a fluorescent, chiral coordination polymer was synthesized with a novel topology for differential interaction with chiral Mosher’s acids to provide a special quenching-based fluorescent signal …”

Section: Sensingmentioning

confidence: 99%

Recent Advances in Separation and Analysis of Chiral Compounds

Yan

2023

Anal. Chem.

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“…The fluorescence quenching efficiency was further analyzed using the Stern–Volmer (SV) equation, I 0 / I = K SV [Q] + 1, in which K SV is the quenching constant, [Q] is the molar concentration of histidine, and I 0 and I are the fluorescence intensities before and after the addition of the histidine solution, respectively. 41,42 The K SV constants calculated through the SV equations for d -histidine and l -histidine are 2.1 × 10 2 M −1 and 9.2 × 10 2 M −1 , respectively, in which the enantioselectivity of ( R )-Zn + l -histidine over ( R )-Zn + d -histidine is evident in the SV plots (Fig. 5c).…”

Section: Resultsmentioning

confidence: 96%