Fluorescent Imprinted Polymers Prepared with 2-Acrylamidoquinoline as a Signaling Monomer

Abstract

[structure: see text] A cyclobarbital-selective molecularly imprinted polymer was prepared using a fluorescent functional monomer, 2-acrylamidoquinoline. This monomer was designed to increase in fluorescence intensity upon hydrogen bonding to the cyclobarbital guest. The resultant imprinted polymers exhibited the enhancement of the fluorescence intensity when cyclobarbital was bound. Our results show that this fluorescent responsive imprinting method could be useful in the development of sensors for quantification of nonfluorescent compounds.

Design of fluorescent materials for chemical sensing

“…Recently, a new fluorescent imprinted polymer that responds to the binding event with a high enhancement in fluorescence intensity has been reported by Takeuchi and co-workers. 117 The co-polymerization of ethylene glycol dimethylacrylate, cross-linker, and the functional monomer 2-acrylamidoquinoline (1) (Fig. 5) in presence of cyclobarbital (2) yields a fluorescent hydrogen-bonded polymer able to bind selectively to the imprinted analyte.…”

Biosensing Applications of Molecularly Imprinted Nanomaterials

“…An amperometric morphine sensor has been developed where the analyte morphine is selectively enriched on an MIP film and subsequently quantified by electrooxidation [117]. So far, the studies on the development of MIP-based sensors, in particularly electrochemical [88,89,[116][117][118][119][120][121][122][123][124][125][126] and optical [127][128][129][130][131][132][133][134][135][136][137] sensors, have been dramatically reported. At the same time, mass-sensitive transducers are increasing in popularity since the approach has the advantage, theoretically at least, that it can be universally applied to a broad range of targets [42,[138][139][140][141][142][143][144][145].…”

“…Among various signal transducers, optically addressable sensors based on fluorescent "turnon" or "turn-off" mechanism have been demonstrated to be highly desirable for a variety of small-molecule analytes in many challenging environments, due to their high signal output and feasible measurements [12,20,44]. Great efforts have recently been made to prepare the fluorescent sensors using molecular imprinting methods [120,[127][128][129][130][131][132]171]. The reason for this lies in the great flexibility and breadth of information obtained by applying optical methods to the analysis of polymer structure, affinity, selectivity, and binding kinetics in the interrogation of polymer-binding mechanisms.…”

“…A fluorescent monomer (2-N-dansyl) ethyl 3,3-dimethylacrylate, was incorporated into an l-tryptophan MIP to develop a competition between the template and an efficient fluorescent quencher p-nitrobenzaldehyde. Takeuchi and coworkers [127] designed and synthesized 2-acrylamidoquinoline as a fluorescent functional monomer with a polymerizable acrylate moiety and a fluorescent hydrogen-bonding moiety. The template cyclobarbital was imprinted into a polymer matrix by using the fluorescent functional monomer, in which the hydrogen bonding of the target into the imprinted sites remarkably enhanced the fluorescence.…”

Molecularly Imprinted Polymers (PIMs) in Biomedical Applications

“…Fluorescent functional monomers are coupled with imprinted sites, exhibiting fluorescence enhancement or quenching upon the analyte binding. In this direction, a 2-acrylamidoquinoline as a fluorescent functional monomer with a polymerizable acrylate moiety and a fluorescent hydrogen-bonding moiety was designed and synthesized (Kubo et al, 2005). The template cyclobarbital was imprinted into a polymer matrix by using the fluorescent functional monomer, in which the remarkable fluorescent enhancement upon the hydrogen bonding of the target into the imprinted sites was observed.…”