On-Surface Synthesis of Porosity-Controlled Molecularly Imprinted Polymeric Receptors for the Biotinyl Moiety

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Suriyanarayanan, SubramanianLinnéuniversitetet,Institutionen för kemi och biomedicin (KOB),Linnaeus Ctr Biomat Chem, BMC;BBCL (author)

On-Surface Synthesis of Porosity-Controlled Molecularly Imprinted Polymeric Receptors for the Biotinyl Moiety

Article/chapterEnglish2024

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American Chemical Society (ACS),2024
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LIBRIS-ID:oai:DiVA.org:lnu-127676
https://urn.kb.se/resolve?urn=urn:nbn:se:lnu:diva-127676URI
https://doi.org/10.1021/acsapm.3c02655DOI

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Language:English
Summary in:English

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Controlled on-surface synthesis of polymer films using amide-based, environmentally friendly, nonionic deep eutectic solvents (ni-DESs) has been developed to regulate the porous features of the films. An appropriate combination of acetamide (A), urea (U), and their methyl derivatives (N-methylacetamide (NMA) and N-methylurea (NMU)) was used to prepare ni-DES. Polymer films were electrosynthesized using 4-aminobenzoic acid (4-ABA) and pyrrole as monomers in ni-DESs. We presumed that the flickering-cluster-like complexes and the extended H-bond networks in ni-DESs enhance the porosity of the polymer films, thus improving permeability features, as reflected in sensor performance. Electrosynthesized polymer films, imprinted with biotin templates (MIPs), have been tested as receptors for biotinylated targets. Molecular dynamics simulations of the prepolymerization mixture revealed the formed complexes between 4-ABA and biotin comprising high-frequency H-bonds. X-ray photoelectron spectroscopy (XPS) and reflection absorption infrared spectroscopy (RAIRS) studies revealed the structural integrity in the polymer films irrespective of the medium. Scanning electron microscopy (SEM) and electrochemical impedance spectroscopy (EIS) measurements showed a highly corrugated and porous nature for MIPA-U and MIPNMU-U when prepared in A-U and NMU-U ni-DESs. Atomic force microscope (AFM) studies support these observations, displaying an enhancement in the surface roughness from 1.44 nm (MIPaqueous) to 23.6 nm (MIPNMU-U). QCM analysis demonstrated a remarkable improvement in sensitivity of MIPA-U (17.99 +/- 0.72 Hz/mM) and MIPNMU-U (18.40 +/- 0.81 Hz/mM) films toward the biotin methyl ester (BtOMe, biotin derivative) than the MIPaqueous film. The chemosensor devised with the above MIP recognition films selectively recognized BtOMe (LOD = 12.5 ng/mL) and biotinylated biomolecules, as shown by the stability constant K-s values (MIPA-U = 1442 and MIPNMU-U = 1502 M-1). The porous network generated in the polymer films by the flickering-cluster-like complexes present in the ni-DES facilitates the analyte diffusion and recognition. We propose this ni-DES as an economically advantageous and environmentally friendly alternative to conventional ionic liquids and organic solvents in polymer synthesis and to influence polymer morphology for developing hierarchical materials.

Subject headings and genre

NATURVETENSKAP Kemi Polymerkemi hsv//swe
NATURAL SCIENCES Chemical Sciences Polymer Chemistry hsv//eng
biotin biosensor
electropolymerization
molecularlyimprinted polymer
nonionic deep eutectic solvent
porous polymer films
quartz crystal microbalance
Organic Chemistry
Organisk kemi

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Olsson, Gustaf D.Linnéuniversitetet,Institutionen för kemi och biomedicin (KOB),Bioorgan & Biophys Chem Lab, SE-39182 Kalmar, Sweden.,Linnaeus Ctr Biomat Chem, BMC;BBCL(Swepub:lnu)guolaa (author)
Nicholls, Ian A.Linnéuniversitetet,Institutionen för kemi och biomedicin (KOB),Linnaeus Ctr Biomat Chem, BMC;BBCL(Swepub:lnu)nniia (author)
LinnéuniversitetetInstitutionen för kemi och biomedicin (KOB) (creator_code:org_t)

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In:ACS Applied Polymer Materials: American Chemical Society (ACS)6:2, s. 1470-14822637-6105

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