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Induced-Fit Recognition by a Calixarene–Pyrene Conjugate for Single- and Dual-Wavelength Fluorescence Sensing in Water
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Orientador(es)
Resumo(s)
The discovery of fluorescence receptors that selectively bind small molecules with high affinity in aqueous media is critical for the development of new sensing and bioimaging assays. We herein report a new fluorescence receptor-dye chemosensor based on the monofunctionalization of p-sulfonatocalix[4]arene (SC4) receptor with pyrene (SC4-4Py). The SC4-4Py conjugate was found to retain the exceptional binding properties of SC4, allowing the high-affinity recognition of neurotransmitters, amino acids, and biogenic amines in aqueous solution and their optical detection. The SC4-4Py chemosensor operates through a photoinduced electron transfer (PET) mechanism triggered by conformational changes in the calixarene structure upon binding, allowing single-wavelength fluorescence detection of target analytes and its expansion into a dual-wavelength ratiometric indicator displacement assay (IDA) that relies on competitive PET between the pyrene and non-covalently bound lucigenin dye.
Descrição
This work was financed by national funds from FCT—Fundaçãopara a Ciência e a Tecnologia, I.P., under the scope of the projectUID/50006/2023 of the Associate Laboratory for Green Chemistry- LAQVREQUIMTE. FCT is also acknowledged for supporting the National Portuguese NMR Network (ROTEIRO/0031/2013-PINFRA/22161/2016,cofinanced by FEDER through COMPETE 2020, POCI, PORL, andFCT through PIDDAC).
Publisher Copyright:
© 2026 The Author(s). Chemistry – A European Journal published by Wiley-VCH GmbH.
Palavras-chave
calixarenes chemosensors host-guest systems induced-fit recognition ratiometric probes Catalysis General Chemistry Organic Chemistry