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November 28, 2022
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Hybrid Gold

BINOL-Containing Chiral Porous Polymers as Platforms for Enantiorecognition

Publicated to: ACS Applied Materials & Interfaces. 14 (48): 53936-53946 - 2022-01-01 14(48), DOI: 10.1021/acsami.2c18074

Authors: Valverde-González A, Borrallo-Aniceto MC, Pintado-Sierra M, Sánchez F, Arnanz A, Boronat M, Iglesias M

Affiliations

CSIC, Inst Ciencia Mat Madrid, Madrid 28049, Spain - Author
CSIC, Inst Quim Organ Gen, Madrid 28006, Spain - Author
Departamento de Química inorgánica, Universidad Autónoma de Madrid, Cantoblanco, Madrid 28049, Spain. - Author
Instituto de Ciencia de Materiales de Madrid, CSIC, C/ Sor Juana Inés de la cruz, 3, Madrid 28049, Spain. - Author
Instituto de Química Orgánica General, CSIC, C/ Juan de la Cierva, 3, Madrid 28006, Spain. - Author
Instituto de Tecnología Química, Universitat Politècnica de València- Consejo Superior de Investigaciones Científicas (UPV-CSIC), Avenida de los Naranjos s/n, 46022 Valencia, Spain. - Author
Sorbonne Univ, CNRS, Inst Parisien Chim Mol, Equipe Chim Polymeres, 4 Pl Jussieu, F-75005 Paris, France - Author
Univ Autonoma Madrid, Dept Quim Inorgan, Madrid 28049, Spain - Author
Univ Politecn Valencia, Consejo Super Invest Cient, Inst Tecnol Quim, Valencia 46022, Spain - Author
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Abstract

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, 1,3,5-triethynyl-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 iso-propenyl 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.

Keywords

acidasymmetric-synthesisbinol building blocksconjugated microporous polymerscovalent triazine frameworksdesignenantioselective recognitionfluorescenceligandsseparationterpenesBinol building blocksChiral porous polymersEnantioselective fluorescent recognitionEnantioselective recognitionFluorescenceTerpenes

Quality index

Bibliometric impact. Analysis of the contribution and dissemination channel

The work has been published in the journal ACS Applied Materials & Interfaces due to its progression and the good impact it has achieved in recent years, according to the agency WoS (JCR), it has become a reference in its field. In the year of publication of the work, 2022, it was in position 55/344, thus managing to position itself as a Q1 (Primer Cuartil), in the category Materials Science, Multidisciplinary.

From a relative perspective, and based on the normalized impact indicator calculated from World Citations from Scopus Elsevier, it yields a value for the Field-Weighted Citation Impact from the Scopus agency: 1.89, which indicates that, compared to works in the same discipline and in the same year of publication, it ranks as a work cited above average. (source consulted: ESI Nov 13, 2025)

Specifically, and according to different indexing agencies, this work has accumulated citations as of 2025-12-08, the following number of citations:

  • WoS: 3
  • Scopus: 10

Impact and social visibility

From the perspective of influence or social adoption, and based on metrics associated with mentions and interactions provided by agencies specializing in calculating the so-called "Alternative or Social Metrics," we can highlight as of 2025-12-08:

  • The use, from an academic perspective evidenced by the Altmetric agency indicator referring to aggregations made by the personal bibliographic manager Mendeley, gives us a total of: 7.
  • The use of this contribution in bookmarks, code forks, additions to favorite lists for recurrent reading, as well as general views, indicates that someone is using the publication as a basis for their current work. This may be a notable indicator of future more formal and academic citations. This claim is supported by the result of the "Capture" indicator, which yields a total of: 7 (PlumX).

With a more dissemination-oriented intent and targeting more general audiences, we can observe other more global scores such as:

  • The Total Score from Altmetric: 1.
  • The number of mentions on the social network X (formerly Twitter): 1 (Altmetric).

It is essential to present evidence supporting full alignment with institutional principles and guidelines on Open Science and the Conservation and Dissemination of Intellectual Heritage. A clear example of this is:

  • The work has been submitted to a journal whose editorial policy allows open Open Access publication.
  • Assignment of a Handle/URN as an identifier within the deposit in the Institutional Repository: https://repositorio.uam.es/handle/10486/713941

Leadership analysis of institutional authors

This work has been carried out with international collaboration, specifically with researchers from: France.

the author responsible for correspondence tasks has been ARNANZ LARA, AVELINA.

Awards linked to the item

Authors acknowledge Grants PID2020-112590GB-C22 and PID2020-112590GB-C21 funded by MCIN/AEI/10.13039/501100011033. A.V.G. thanks Ministerio de Universidades for FPU17/03463.