Green and Rapid Synthesis of Durable and Super-Oil (under Water

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Letter

Green and Rapid Synthesis of Durable and SuperOil (under water) and Water (in Air) Repellent Interfaces Adil Majeed Rather, and Uttam Manna ACS Appl. Mater. Interfaces, Just Accepted Manuscript • DOI: 10.1021/acsami.8b06924 • Publication Date (Web): 06 Jul 2018 Downloaded from http://pubs.acs.org on July 7, 2018

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ACS Applied Materials & Interfaces

Green and Rapid Synthesis of Durable and Super-Oil (under water) and Water (in Air) Repellent Interfaces Adil M. Rather, Uttam Manna* Department of Chemistry, Indian Institute of Technology-Guwahati, Kamrup, Assam 781039, India Supporting Information ABSTRACT: In this letter, a single polymer is rapidly and covalently transformed into chemically reactive and functional bulk polymeric coatings through catalyst free mutual chemical reaction between acrylates and amine groups at ambient condition—in absence of any external reaction solvent, which is unprecedented in the literature. This facile and green chemical approach provided a common basis for achieving two distinct biomimicked wettability—that are superhydrophobicity (lotus-leaf mimicked) in air and superoleophobicity (fish-scale inspired) under water. The essential chemistry that conferred bioinspired wettability was optimized in the hierarchically featured polymeric material by post covalent modulation of chemically reactive polymeric material with primary-amine containing small molecules—that are glucamine and octadecylamine. The inherently sticky and ‘chemically-reactive’ polymeric material having appropriate hierarchical topography is highly capable of providing substrate independent (irrespective of chemical compositions, mechanical strength of the substrates) stable coatings with robust bio-inspired (i.e. lotus leaf and fish scale) wettability. Keywords: superhydrophobicity, superoleophobicity, chemically reactive, Michael addition reaction, polymeric coating, rapid gelation

INTRODUCTION The ‘chemically-reactive’ interfaces that provided facile and robust avenue for tailoring various relevant chemical functionalities,1-14 is fundamentally interesting and important for synthesizing smart and functional materials that have wide range of potential applications—including immobilization of desired bio-active molecules, synthesis of cell on a chip, controlled release of small molecules, multi biofunctionalization, smart sensing of various relevant chemical toxins and developing patterned interfaces etc.1-17 Most often, such chemically reactive functional interfaces are ultrathin (in the scale of nanometre) and mostly featureless, and were prepared commonly through multistep deposition processes—that are layer-by-layer (LbL) deposition of reactive polymer and chemical vapor deposition (CVD)—followed by uncontrolled polymerization process.1-7, 9-11 In the recent past, Lynn and coworker18-19 extended this concept of chemically reactive coating, and strategically synthesized hierarchically featured and chemically ‘reactive’ interface for developing lotus leaf inspired durable wettability. The lotus-leaf mimicked extremely water repellent interfaces are being well recognized for several prospective applications including open microfluidics, high throughput screening of drug, controlled drug delivery, oil/water separation etc.20-22 In general, the conventional and thin artificial superhydrophobic coatings are developed through appropriate co-optimization of 1) essential chemistry and 2) topogra-

phy—only over the few nanometer across the thickness of the artificial biomimicked interface.23-26 Thus, the slight perturba-

tion in either chemistry or topography in the conventional

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design is expected to cause severe and permanent damage to the embedded special wettability.27-29 In comparison to conventional approach, the hierarchically featured and chemically ‘reactive’ thick coatings inherently yielded highly durable biomimicked interfaces. Such chemically reactive approaches are inherently capable of providing a facile basis for tailoring essential chemistry—three dimensionally, and allowed to trap metastable air across the thickness of the material and eventually provided bulk superhydrophobicity.19 Thus, the synthesized bulk superhydrophobic materials became highly durable and capable of sustaining severe physical damages including physical erosion of the synthesized material. However, the examples of such chemically ‘reactive’ and hierarchically featured interfaces are very rare in the literature, and functional polymers are mostly associated—following tedious multistep/complex synthetic procedures in the previous reports.18-19 Single polymer based rapid synthesis of chemically reactive and hierarchically featured interfaces—without using any catalyst and reaction solvent at ambient conditions is unprecedent-

ed in the literature. Moreover, this single approach is extended in synthesis of other nature inspired wettability—that is fishscale mimicked underwater superoleophobicity and such bio mimicked interfaces demand distinct chemical optimization. Here, in this communication, branched polyethylenimine (BPEI, Figure 1A) is spontaneously converted into ‘chemically reactive’ and functional polymeric material through solventfree and catalyst-free mutual reaction with another liquid reactants—that is dipentaerythritol penta-acrylate (5Acl, Figure 1A). On mixing the polymer (BPEI) and small molecules (5Acl)—in absence any external organic/aqueous solvents; a chemically reactive polymeric material was spontaneously (within 30 s) formed through facile Michael addition reaction (Figure 1B) between amine and acrylate groups at ambient conditions as shown in Figure 1C. This ‘reactive’ and inherently sticky polymeric material was then exploited in developing substrate independent functional coatings—with lotus leaf (extremely water-repellent interface; Figure 1D) and fish scale (underwater super-oil-repellent interface; Figure 1E) inspired


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ACS Applied Materials & Interfaces artificial and durable bulk-wettability, after covalent postmodifications with appropriate small molecules (e.g. octadecylamine, glucamine). RESULTS AND DISCUSSIONS In the past, Michael addition reaction is strategically exploited in synthesis of various important class of small molecules, biodegradable polymers for drug delivery, functional surface modifications, anti-bio-fouling coating etc.30-36 Recently, our group has introduced 1,4 conjugate addition in the synthesis of reactive polymeric nanocomplex (RNC) in alcoholic solvents and that RNC was strategically used to form freestanding superhydrophobic monolith for oil/water separations,30-31 and such nanomaterial was also strategically associated into ‘reactive’ multilayer construction in alcoholic solvents through consecutive (40 times) use of Michael addition reaction—and that multilayer was successfully used in tailoring liquid-wettability under water.32 Here, in this current study, we adopted an unprecedented approach for rapid and green synthesis of covalently cross-linked, hierarchically featured and chemically reactive polymeric material—without using any external reaction solvent. The ecofriendly, solventand catalyst-free green synthesis approach provided facile and rapid basis for adopting various important biomimicked interfaces that have enormous importance and prospective applications in practically relevant settings. In this current approach, 1) the strategic use of chemistry 2) the synthesis procedure and 3) the synthesized material is completely different from previous reports. Series of controlled studies were performed, where the molar ratio (‘mole to mole’ ratio) of the liquid reactants (BPEI (the mole amount is calculated with respect to the repeating unit) and 5Acl) were varied (from 1:3 to 1:5; BPEI:5Acl) to achieve biomimicked wettability through controlled optimization of a) essential topography and b) appropriate chemistry. The colorless mixture (Figure 2A, with molar ratio 1 (BPEI): 3 (5Acl)) of liquid polymer (BPEI) and small molecules (5Acl) were mixed rapidly to form an opaque gel (Figure 2B) within 30 S as shown in Fig-

ure S1. The synthesized polymeric gel was hydrophilic with water contact angle (WCA) of 730, and this WCA was increased from 73ᵒ to 85ᵒ after treatment of the polymeric gel with octadecylamine (ODA) molecules. This change in water wettability was further improved with varying the molar ratio of the selected reactants (BPEI and 5Acl; 1:4) in the reaction mixture. On increasing the content of 5Acl in the reaction mixture, the gel materials became more hydrophobic (with WCA of 120°) after ODA treatments. The reaction mixture of BPEI/5Acl with 1:5 molar ratio yielded another hydrophilic material (Figure 2D-E)—but that became superhydrophobic after ODA treatment, and the water droplet (red color aids visual inspection) beaded on the same gel material with an advancing water contact angle above 150° and contact angle hysteresis below 10° as shown in Figure 2F-G. This change in wettability is mainly attributed to the inherent primary amine ‘reactivity’ of the synthesized polymeric gel. The synthesized gel was loaded with residual acrylate groups as revealed with standard FTIR spectral study.10 The IR peaks (Figure 2H) at

1735 cm-1 and 1410 cm-1—which corresponds to the carbonyl stretching and symmetric deformation of the C−H bond for the β carbon of the vinyl groups, unambiguously revealed the existence of acrylate groups in the synthesized polymeric gel. Further, the depletion of the IR peak at 1410 cm-1 with respect to 1735 cm-1 (the internal standard, where carbonyl groups remained unperturbed in Michael addition reaction) after the post-modification of the material with ODA molecules, independently confirmed a) the presence of amine ‘reactive’ func-



tionality (i.e. residual acrylate groups) in the material and b) the covalent integration of desired chemistry in the material through robust 1,4 conjugate addition reaction, and this optimized chemistry in the polymeric gel conferred the biomimicked superhydrophobicity. The density and surface area of the synthesized superhydrophobic material were 0.93 g/cm3 and 1.809 m²/g respectively. The compressive modulus of the superhydrophobic material was calculated to be 1380 ±94 kPa (Figure S3A) and the thermal stability of the prepared material was noticed to be higher in comparison to the native BPEI polymer (Figure S3B). This synthesized polymeric material was capable of displaying inherently durable bulk superhydrophobicity. The entire polymeric gel that was post-modified with ODA molecules, was arbitrarily sliced into two parts to expose the interior of the material and the interiors were observed to be superhydrophobic as the freshly exposed interiors repelled the beaded water droplets with WCA above 150° as shown in Figure S4. Next, a stream of water droplet was observed to readily bounce away after hitting the biomimicked interface, these simple studies supported the existence of durable special wettability. Further, detailed chemical/physical durability tests were conducted to examine the stability of the biomimicked wettability, and those results are discussed later. Next, the microscopic morphology of the polymeric gel was examined with FESEM study, where the top interface of the polymeric gel was noticed to have random porous structures. Such porous topography also exist in the bulk of the polymeric gel (Figure S5E-F), and similar topography was noticed for the polymeric coating on selected substrates (Figure S 5G-H). This porosity appeared, likely due to the removal of unreacted reactants during washing of the polymeric gel material. Thus, the ‘reactive’ polymeric gel is embedded with appropriate hierarchical topography. This facile chemical approach of synthesizing chemically ‘reactive’ and porous polymeric gel allowed to tailor various other wettability through appropriate modulation of chemical functionality in the same polymeric gel material (molar composition of the BPEI and 5Acl mixture was maintained to be 1:5).

The chemically reactive (inherently hydrophilic) polymeric gel become moderately hydrophobic (WCA ~ 107°), highly hydrophobic (120°) to superhydrophobic (>150°) on increasing the carbon number (from C5 to C18) in the primary amine containing small molecules—which was covalently attached on the polymeric gel through 1,4 conjugate addition reaction as shown in Figure 3C and Figure S6, and eventually same material is capable of displaying both homogeneous and heterogeneous wettability. The post covalent modifications of the gel material with various small molecules (having primary amine groups and hydrophobic tails) were characterized with FTIR spectral studies (Figure S7), where the peak at 1410 cm-1 was significantly reduced after post chemical modification with selected small molecules. Furthermore, the same covalently crosslinked (through 1,4 conjugate addition reaction) and chemically reactive gel—which soaked oil under water (See Figure S8A-B), displayed extreme oil repellency under water with advancing oil contact angle (OCA, Figure 3E-F) of above 160° and contact angle hysteresis below 5° after strategic modulation of the ‘reactive’ gel with hydrophilic glucamine molecules. This underwater superoleophobicity is recently emerged as another potential biomimicked (Fish-scale) interface for various prospective applications.37-38The glucamine treated and covalently crosslinked polymeric gel was also capable of displaying bulk superoleophobicity under water as shown in Figure S8E-F. The interior of the material was exposed by arbitrary manual slicing and the beaded oil droplets on the freshly exposed interior of the material was repelled extremely underwater with OCA above 160°—and example of such bulk underwater superoleophobicity is rare in the literature. This chemically ‘reactive’ and inherently sticky gel was further used in coating various substrates irrespective of their chemical composition and wettability, including glass, plastic film, aluminum foil, filter paper and wood surface. A 2.8 g of amine reactive gel—which was prepared just by mixing BPEI and 5Acl (with 1:5 molar ratio) was placed on the surface of selected and cleaned substrates, and spread out with one end of the microscopic glass slide uniformly over 21.6 cm2 area. Then, the extreme oil and water wettability was tailored on covalently cross-linked ‘reactive’ and polymeric coatings (555 µm ±40 µm) through the appropriate selection of chemical modulations (either ODA or glucamine; Figure 4 and Figure S9). This simple approach provided a facile and substrate independent bulk coatings of polymeric materials that are with different biomimicked extreme liquids (oil/water) wettability, and both the oil and the water droplets are beaded with high contact angles (above 150°) and low contact angle hysteresis (below 10°) as shown in Figure 4. The digital


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ACS Applied Materials & Interfaces images in the inset of Figure 4 are representing superhydrophobic (left) and underwater superoleophobic (right) coatings on glass substrate. This current approach did not demand any additional surface modification on the selected substrates. The coatings on Al foil, glass and filter paper were strategically exposed to freshly exposed adhesive tape with 100 g of applied load, and during the peeling of the adhesive tape,23, 27, 32 some top portion of the film was transferred to the adhesive tape. However, the superhydrophobicity remained embedded with the remaining portion of the coating on the selected substrates, even after this severe physical damage as shown in Figure S10. Furthermore, this simple study revealed the existence of strong interfacial interaction between the substrate and deposited film—likely through nonspecific hydrogen bonding and electrostatic interaction, similar to that of nonspecific interactions in Mussel inspired coatings.39 The biomimicked coatings were exposed to 100 g of sand from 15 cm distance, and the embedded special wettability was found to be unaffected (Figure S10 G-H). Next, the superhydrophobic coating was exposed to UV irradiations at 254 nm and 365 nm for 5 days and extreme water repellency was observed to be unaltered with advancing WCA above 150° as shown in Figure S11. Further, this biomimicked interfaces were exposed to various complex aqueous phases including extremes of pH, artificial sea water ad river (Brahmaputra River, Guwahati, India) water and the polymeric coating continued to repel these chemically complex phases with advancing WCA above 150° and contact angle hysteresis below 10° (Figure S12). The current simple and rapid chemical approach provided a single avenue for synthesis of chemically reactive and covalently cross-linked polymeric coatings that capable of displaying two distinct and durable biomimicked wettability—that are under water superoleophobicity and superhydrophobicity in air. This approach could be further exploited in developing functional bio-interfaces and chemically patterned interfaces.15-17 Thus, this material could be useful in synthesis of anti-bio-fouling coating, drug delivery, oil-resistant coating, anti-corrosive coatings, tissue engineering, developing functional patterned interfaces etc.1-17, 27-29, 40 CONCLUSION In conclusion, a chemically ‘reactive’ and covalently crosslinked functional polymeric interface is introduced through a solvent/catalyst-free facile and rapid 1,4 conjugate addition reaction. Further, the residual acrylate groups—which made this polymeric material inherently chemically reactive, was strategically used in covalent and controlled modulation of various chemistries in the synthesized material for developing inherently durable and highly prospective biomimicked interfaces—including underwater superoleophobicity and superhydrophobicity in air. This simple and environmentally friendly single chemical approach could be useful in synthesizing other functional interfaces (i.e. various chemically patterned interfaces, patterned wettability etc.) for various smart and prospective applications.

ASSOCIATED CONTENT Supporting Information

The Supporting Information is available free of charge on the ACS Publications website, the attached supporting in-

formations accounting detail experimental procedures, demonstration of rapid gelation of reaction mixture, FTIR characterization of residual acrylate functionality at different compositions of reaction mixtures, bulk wettability, FESEM characterization of different gels, effect of chemical modulation on embedded water wettability in air, FTIR characterization of different chemical modifications, investigation of oil wettability under water, substrate independent fish-scale and lotus leaf inspired coatings, physical/chemical durability tests.

AUTHOR INFORMATION Corresponding Author *[email protected].

Notes The authors declare no competing financial interests.

ACKNOWLEDGMENT We thank Department of Biotechnology (DBT, India) (BT/PR21251/NNT/28/1067/2016), Department of Science and Board of Research in Nuclear Sciences (BRNS) (34/20/31/2016BRNS, DAE-YSRA), Department of Atomic Energy (DAE) for financial support. We are thankful to CIF, Department of Chemistry and Indian Institute of Technology-Guwahati for their continuous support and help in proving infrastructure and instrumental facilities. Mr. Adil Majeed Rather is grateful to IIT-Guwahati for his PhD fellowships from the Institute.

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Green and Rapid Synthesis of Durable and Super-Oil (under Water

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