The chemical interactions of the template molecule are primarily dependent on the choice of polymer

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1 Study of the Surface Morphology of Methyl 4-nitrobenzoate Template Thin-film Molecularly Imprinted Polymers Gary Kaganas Dartmouth College and Center for Nanomaterials Research at Dartmouth, Hanover NH Introduction The study of surface morphology is a useful aid in understanding polymer properties. Polymeric thinfilm surface properties generally reflect features of the particular polymer blend that was used, the chemical atmosphere when it was casted, and interactions between the polymer and the constituents of film. Molecularly imprinted polymers (MIPs) act as recognition systems that function at the molecular level. Traditionally MIPs start out as individual monomers. These monomers are mixed in solution with the target molecule and when in the presence of a crosslinker (e.g., EGDM) and an initiator (e.g., AIBN) polymerize into a fixed configuration around the template molecule. The template molecule is then chemically extracted without changing the polymer structure to create a binding site that is particularly well suited to recognize for the template molecule that was used. In the 'wet process' MIPs are made in solution with an appropriate solvent. The particulars of the process are detailed below. However, within the 'wet process' there the finalizing step is termed the 'dry process' where the solvent must be evaporated. Conventional methods require long drying times or high temperatures. In a process adapted to MIPs, the BelBruno group drastically reduces the evaporation time of the solvent by spin coating the solution at high revolutions onto a suitable substrate. Molecular interactions in the casting solution and the mechanics of the deposition process give rise to either pores or some well defined structure that increases the surface area of the film, thereby facilitating transport to the binding sites. In this study, I studied the deposition chemistry of the template molecule methyl 4-nitrobenzoate by isolating its functional groups. To that end, the effect of the molecule's benzene ring and nitro functional groups were represented by 4-nitrotoluene, the effect of the benzene ring alone was studied with biphenyl, and the benzene ring and ester groups were approximated with benzoic acid. Individual MIPs were made from each of these molecules. MIPs made from molecule templates with carbon chains of the length of a benzene ring, but without the aromaticity, such as methyl hexanoate and adipic acid were also observed. The resulting morphologies of all these polymer-template complexes were carefully recorded to detect any correlation with methyl 4-nitrobenzoate. The chemical interactions of the template molecule are primarily dependent on the choice of polymer

2 used for the MIP films. Poly(4-vinylphenol) is a versatile polymer that is well suited to non-covalent MIPs. It may use the OH molecule on the phenol group to hydrogen bond, and it can also reinforce the strength of pi-pi interactions effected by the monomer's benzene rings by sandwiching molecules between two monomers. Imprinting process BelBruno and his group pioneered a novel imprinting method that bypasses the polymerization step. Instead, in what is called the phase inversion method, a ready-made polymer is mixed in a theta solvent with the target molecule. The polymer is chosen for the affinity between its functional groups to the target molecule using the same rationale for selecting the monomer groups in the initiator method. To ensure a thorough interaction the polymer and template are mixed in solution for an extended period ranging from six to 24 hours. The resulting solution is then cast as a thin-film using a spin coater. Analogous to the polymerization method, when the template molecule is subsequently removed, the vacated polymer retains the configuration of the template molecule at the interaction sites. The phase inversion method has been carried out in non-sterile environments under standard temperature and pressure. No qualitative assessment that I am aware of has been made to compare the merits of the new phase inversion method to the traditional process, but several families of molecularly imprinted polymers have been made successfully with this technique. Procedure Every molecularly imprinted polymer produced followed a standard procedure. Equal amounts of polymer and template, by weight, were mixed in solution in the presence of a solvent. For the purposes of this study two solvents where used, dimethylformamide (DMF) and methyl ethyl ketone (MEK). DMF is a widely used organic solvent with a molecular formula C 3 H 7 NO. This molecular configuration has a resonance structure that serves to increase the electronegativity of the oxygen atom increasing its likelihood of hydrogen bonding. With a chemical formula C 4 H 8 O, MEK resembles the DMF solvent but lacks a nitrogen molecule and a resonance structure. The polymer-template complex composes at least 20% of the solvent weight. The solution is mixed on a magnetic stirrer for six hours. The molecularly imprinted polymer is coated on a substrate as a thin-film. The film is produced using a spin-casting method. The film deposits evenly on the substrate as it rotates at 7,000 rpm for a 30-second cycle. While the polymer-template complex spreads uniformly on the surface of the substrate during the spin cycle the solvent material evaporates. Thin-films are casted on glass microscope slips for AFM applications and on NaCl plates for IR analysis.

3 All the templates used in this experiment are soluble in toluene. To extract the template, the MIP is submerged in toluene for two minutes. The substrate is blotted dry with Kimwipes. Analysis Infrared Spectroscopy Infrared Spectroscopy analyses were performed on all the polymer-template complexes used in this experiment for solutions made in dimethylformamide and methyl ethyl ketone solvents. As a control, IR spectra were taken of polymer-only preparations in both solvents. IR spectra of DMF-based solutions of all the observed polymer-template complexes confirmed that production and extraction of that target molecule was successful for all trials. On the next page are spectra of benzoic acid compared to a polymer-only spectrum that demonstrates how the analysis was confirmed. The first graph shown in Figure 1 corresponds to the IR spectrum of benzoic acid in PVP as produced, i.e. before extracting the template molecule. The characteristic peaks that distinguish benzoic acid from the PVP polymer are observed at 706 cm -1 and 932 cm -1, both corresponding to aromatic peaks; 1,292 and 1,326 cm -1 which are carboxylic acid peaks; and 1686 cm -1 which identifies a carbonyl peak. After extraction with toluene, these peaks disappear in the empty film as shown in Figure 1 (b), and the spectrum resembles the original PVP control almost exactly (Figure 1 (c)). Table 1 summarizes the vanishing peaks for the template-extracted polymer-template complexes. The characteristic peaks for most of the MIPs prepared did indeed disappear when performing IR spectra DMF solutions, implying a successful extraction. However, as the table readily demonstrates, characteristic template molecule peaks for MEK solutions where less conspicuous and their disappearance upon extraction infrequent. At this point I consider the trials inconclusive and further tests should be performed. Template Molecule Aromatic Carboxylic Acid Carbonyl Nitrous DMF MEK DMF MEK DMF MEK DMF MEK 4-nitrotoluene 1,655 1,343 Biphenyl 1,650 Benzoic acid ,300 1,340 1,690 Table 1. The polymer-template complex will exhibit a range of discrete resonant peaks. Upon extraction the template molecule peaks should disappear to confirm the extraction was performed successfully. The table lists the disappearing peaks of three template molecules.

4 Figure 1. Comparison of IR spectra of benzoic acid (a) as produced and (b) after extraction to a control spectrum of (c) PVP only.

5 Figure 2. AFM images of (a) PVP polymer dissolved in DMF and (b) PVP in MEK. Atomic Force Microscope Since the primary goal of the research project was to study the morphology of the MIP thin-films, much time was spent acquiring images of the films. Because the investigation is intended as a proof of concept, the aims of the morphology studies were entirely qualitative. Structures that differed significantly from the control samples were of particular interest. As in the IR studies, all the polymertemplate complexes were observed in both the DMF and MEK solutions. The general surface structure of Methyl 4-nitrobenzoate presents itself in long, thick branches with well defined borders. Figure 3 shows this branching phenomenon which appears in both the MEK and DMF samples. By analyzing the morphology of the other template molecules included in the study it might be possible to narrow down the factors that result in this interesting structure. Figure 3. AFM images of (a) methyl 4-nitrobenzoate template MIP film dissolved in DMF and (b) methyl 4-nitrobenzoate template MIP film in MEK. The dimensions of both images are 13 m x 13 m.

6 Figure 4. AFM images of (a) 4-nitrotoluene, (c) biphenyl, and (e) benzoic acid template MIP films dissolved in DMF; and (b) 4-nitrotoluene, (d) biphenyl, and (f) benzoic acid template MIP films in MEK. The dimensions of both images are 13 m x 13 m. Molecularly imprinted polymers made with 4-nitrotoluene template molecules had minimal structure. In Figure 4 (a), a 4nitrotoluene polymer-template complex is mixed in DMF solvent. AFM observations show that the surface relief is mostly flat, punctuated by relatively large isolated particles. The absence of pore formation also implies that the polymer-template complex attached more strongly to the substrate than the solvent, leaving the solvent on the surface where it simply evaporated during the spin casting process. When mixed in with MEK solvent, the 4-nitrotoluene complex exhibited slightly more structure. The surface was no longer flat, nonetheless large particles where still observed as show in Fig 4 (b). The biphenyl template MIPs presented more interesting surface phenomena. The micrograph in Figure 4 (c) is a biphenyl in DMF solution, and Figure 4 (d) shows biphenyl prepared with MEK as solvent. It is immediately apparent that the MEK sample exhibits more structure. The slightly darker regions with clearly marked outlines are likely areas where the solvent evaporated. It is also important to note that both samples have a similar degree of porosity.

7 The benzoic acid samples showed the most developed structure, approximating the structure observed in methyl 4-nitrobenzoate. The overall picture is qualitatively the same for both the DMF and MEK solvent solution. While the clear branching is visible in Figure 4 (e) for the DMF sample, the pattern is preserved in Figure 4 (f) showing the MEK solution. The differences are most likely not a result of varying interactions, but rather the vapor pressure of the solvent and the mechanics involved in depositing the thin-film. In an attempt to isolate the interaction of the benzoic acid ring in the polymer-template complex, methyl hexanoate and adipic acid were used as a template molecule. Methyl hexanoate was produced both in DMF and MEK solutions. An adipic acid MEK solution was prepared, but it turned out to be mostly insoluble in MEK characterization was not pursued. Discussion As mentioned earlier, the morphology of the film surface is related to the polymer properties. In particular, the structures observed are affected by the polymer-template complex interactions, the complex-substrate affinity, the solvent-complex interaction and the solvent-substrate interaction. The mechanics of the spin casting deposition as well as the atmospheric conditions will contribute to varying degrees. The nature of the between the compounds studied are relatively well understood and can be reliably predicted. The knowledge of this bonding framework proved useful in explaining the observed structure. Figure 5. AFM image of (a) 4-nitrophenol with a (b) 3-D representation of the surgface morphology. The methyl 4-nitrobenzoate molecule forms a non-covalent complex with the poly(4-vinylphenol) polymer. Theoretically, methyl 4-nitrobenzoate can either hydrogen bond or use its nitro group to form weak polar bonds with the OH group in the phenol of the PVP polymer. Pi-pi interaction can also arise,

8 but these are very weak and are not the primary basis of interaction. Observations of the 4-nitrotoluene sample allowed the study of the nitro group interaction. The difference between the texture in Figure 4 (a) and (b) can be explained by the weak interaction of the polymer and the nitro group in the template molecule with the solvent. Before it evaporates, the solvent will interact with both the template molecule and polymer. The level of interaction of the solvent with the polymer-template complex is negatively correlated with the total interaction of the template and the polymer. More specifically, if the solvent and the template interact, by polar bonding with the nitro group in the case of 4-nitrotoluene, or if the solvent interacts with the polymer, or if the solvent interacts with both the template molecule and the polymer (as is commonly the case) then both the template molecule an the polymer have less interaction sites available and therefore form a more tenuous bond. The resonant structure of DMF is more likely to interact with the nitro group of 4-nitrotoluene and the OH in the phenol group of PVP as compared to MEK, and may impair the widespread formation of the polymer-template complex. This may account for the lack of structure seen in Figure 4 (a). Following from this line of thought, biphenyl, composed of two benzene rings, did not exhibit much structure when casted from a DMF solution. Biphenyl can only bond to the PVP via pi-pi interaction at the benzene ring of the vinylphenol monomer. The stronger hydrogen bonding of the DMF solvent should be dominant. Predictably, the pores observed in the images of the biphenyl template in DMF are not very different from the poring of the PVP control in DMF. In the MEK solution some porosity was visible, however the raised surface indicates that a significant portion of the solution formed into a polymer-template complex. This is corroborated from the basins between these structures that were formed by the evaporation of the solvent, implying that the solvent collected outside the polymertemplate complex. Benzoic acid molecules can hydrogen bond at the acid group with the OH in the phenol group of a PVP monomer. The resonant structure of the acid group can hydrogen bond either at the OH site or at the carbonyl group. This gives is a significant advantage over the one hydrogen bonding site in DMF or MEK. This may explain why the micrographs of both complexes show a similar overall pattern. In fact Figure 6 is an image taken from the same film as shown in Figure 4 (e), but in a different location of that film. The resemblance is easy to appreciate. The widespread formation of Figure 6. Alternate surface morphology of a benzoic acid template MIP. Image scale is 13 m.

9 polymer-template complex forces the solvent to collect outside the complex and evaporate, leaving behind the grooving evident in the images. To better study the impact of hydrogen bonding in aromatic molecules samples were made with 4- nitrophenol, which uses the phenol functional group to form a strong hydrogen interaction. This is evidenced by the dense polymer-template complex structure and the high relief shown in Figure 5 (a) and (b), respectively. Following the arguments used above, and comparing to the benzoic acid samples, it becomes apparent that the stronger the interaction potential of the template molecule the more pronounced the surface features. Moreover, the similarities in the grooving of the surface between this sample and the benzoic acid sample may imply that the polymer-template complex is interacting with the substrate leaving the solvent on the surface of the film where it eventually collects and evaporates. To study the effect of the benzoic ring more closely we also prepared samples using methyl hexanoate. AFM images of MIP films prepared with methyl hexanoate show completely flat surfaces for both the DMF and MEK solutions. While the opportunity to hydrogen bond should be high at the methyl functional group, methyl hexanoate is a liquid at STP, a condition that may inhibit the polymer-template complex from precipitating when being spin casted. The resulting liquid complex most likely evaporates with the solvent. As mentioned above, adipic acid, composed of a similar carbon chain as methyl hexanoate was prepared. Unfortunately, the acid was almost insoluble in MEK and a thin-film could not be prepared. There was not enough time to prepare a DMF solution. Conclusion Methyl 4-nitrobenzoate is an aromatic molecule composed of a benzene ring a methyl ester group and a nitro group on the fourth position. All these components were isolated to study the interaction mechanism of the complete molecule. MIPs were prepared using an original phase inversion method pioneered by Dr. BelBruno's group that included a novel spin casting method. Only molecules that could be successfully extracted to form a MIP were of interest. IR Spectroscopy was used to confirm the production and extraction of the template molecules. The study of these molecules was performed by comparing the surface morphology of the thin-film MIP. From these observations it is conjectured that the branched structure of methyl 4-nitrobenzoate is caused as a result of the non-covalent hydrogen bonding and to a much lesser extent the pi-pi bonding at the benzene ring. Further studies must be performed to corroborate this preliminary idea.

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