Controlling Polymorphism in Pharmaceutical Compounds Using Solution Shearing

Guthrie, Stephanie

doi:10.18130/v3tq5rd1v

Cited by 4 publications

(7 citation statements)

References 40 publications

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“…6,25 Recently, a meniscus-guided coating technique, called solution shearing, has drawn great attention as a technique for facile, rapid, and large-area thin-film fabrication. 4,8,26−28 The solution shearing technique is commonly used to deposit organic semiconductors 29 and polymer 28,30 and has been shown to be compatible with a wide range of materials such as pharmaceutical compounds 27 and carbon nanotubes. 31 During solution shearing, the precursor solution that contains the solute of interest is injected between the translating blade and the heated substrate.…”

Section: ■ Introductionmentioning

confidence: 99%

Meniscus Guided Coating and Evaporative Crystallization of UiO-66 Metal Organic Framework Thin Films

Jung

Verma

Robinson

et al. 2021

Ind. Eng. Chem. Res.

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Thin-film fabrication of metal organic frameworks (MOFs) has been explored for a range of applications, including separations, catalysis, sensing, and charge transport. However, many fabrication techniques have obstacles, including slow crystallization, control over film thickness, and control over crystallinity. Recently, a meniscus-guided coating technique, called solution shearing, has been shown to create MOF thin films within minutes and with control over the film thickness. However, there have been no previous reports of solution shearing based evaporative crystallization of zirconium-based MOFs, which have been widely studied for the aforementioned applications. Here, for the first time, we show that (i) the zirconium 1,4-dicarboxybenzene MOF, UiO-66, can be formed using evaporative crystallization during solution shearing, and (ii) a wide range of parameters can be tuned to control the film thickness, coverage, and crystallinity. Finally, we bring the solution shearing technique closer to separation applications by growing a full film of UiO-66 crystals up to the resolution of scanning electron microscopy (SEM) on anodic alumina oxide (AAO). This is the first instance of UiO-66 crystals being formed using an evaporative crystallization-based flow coating method, and solution shearing shows the promise to be applicable to form large area zirconium-based MOF crystals in a rapid manner (within seconds to minutes).

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Section: ■ Introductionmentioning

confidence: 99%

Meniscus Guided Coating and Evaporative Crystallization of UiO-66 Metal Organic Framework Thin Films

Jung

Verma

Robinson

et al. 2021

Ind. Eng. Chem. Res.

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“…For active pharmaceutical ingredients (APIs) or simple drugs, thin film fabrication technologies have not yet been used extensively, as upscaling into mass production might require fabrication processes distinct from already established ones. For the sake of finding new polymorphs of drugs with the intention of reaching better solubility or overcoming patent issues, different film deposition techniques have been employed, including spin coating, 10−12 drop casting, inkjet printing, solution shearing, 13 dip coating, and vacuum deposition among others. The drug dissolution from such layers is often faster compared to bulk systems.…”

Section: ■ Introductionmentioning

confidence: 99%

Surface Induced Phenytoin Polymorph. 1. Full Structure Solution by Combining Grazing Incidence X-ray Diffraction and Crystal Structure Prediction

Braun

Rivalta

Giunchi

et al. 2019

Crystal Growth & Design

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Understanding the behavior and properties of molecules assembled in thin layers requires knowledge of their crystalline packing. The drug phenytoin (5,5-diphenylhydantoin) is one of the compounds that can be grown as a surface induced polymorph. By using grazing incidence X-ray diffraction, the monoclinic unit cell of the new form II can be determined, but, due to crystal size and the low amount of data, a full solution using conventional structure solving strategies fails. In this work, the full solution has been obtained by combining computational structure generation and experimental results. The comparison between the bulk and the new surface induced phase reveals significant packing differences of the hydrogen-bonding network, which might be the reason for the faster dissolution of form II with respect to form I. The results are very satisfactory, and the method might be adapted for other systems, where, due to the limited amount of experimental data, one must rely on additional approaches to gain access to more detailed information to understand the solid-state behavior.

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“…In this region, a limited number of nucleation events occur and growth is dominant, producing large areas of aligned crystals, as seen in other solution shearing studies. 16,25 The alignment can be determined by observing the change in intensity (optical activity) as a function of the sample rotation under cross-polarized light. Rotated crosspolarized images are included in the right column of Figure 23 and ε polymorphs.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…18 Guthrie et al have shown the selective polymorph formation and high control over the crystal morphology for glycine and acetaminophen thin films using solution shearing. 16,19 We build upon these studies to further develop an understanding of the EM crystallization pathways, as well as fabricate thin-film EM crystals for studies on stability and polymorphic interconversion.…”

Section: ■ Introductionmentioning

confidence: 99%

Selective Morphological and Polymorphic Control of CL-20 Thin Films Using Meniscus-Guided Coating

Smith

Guthrie

Dreger

et al. 2021

Crystal Growth & Design

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Controlling the morphology and crystal structure of energetic materials (EMs) is crucial for predictable performance and stability under operational and accidental scenarios. In this work, an EM of interest, hexanitrohexaazaisowurtzitane (CL-20), was crystallized as thin films using a meniscus-guided coating technique termed solution shearing. We observed four distinct morphological regimes within the parameter space, as well as regions with selective formation of the β and γ polymorphs of CL-20. The thin films ranged in thickness from 79 nm to 2.2 μm and in surface coverage from 36.2 to 99.9%. Thermal annealing of films at 180 °C promotes a β-to-γ phase transformation for films with thicknesses >500 nm. Water vapor annealing of films results in a phase transition to α-hydrate. We were unable to attain the ε polymorph in our thin films across all processing conditions, including dissolution and recrystallization, which preferentially forms the β polymorph. Therefore, we show that thin-film confinement stabilizes the β polymorph of CL-20 over the ε polymorph. The results of this work have important implications for EM composites as interfacial recrystallization of the stable bulk ε polymorph may result in the formation of the β polymorph as a thin film at the interface, changing the EM stability. We show that the solution shearing technique provides a promising platform for the study of the interfaces between energetic crystals and polymers in composites.

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Controlling Polymorphism in Pharmaceutical Compounds Using Solution Shearing

Cited by 4 publications

References 40 publications

Meniscus Guided Coating and Evaporative Crystallization of UiO-66 Metal Organic Framework Thin Films

Meniscus Guided Coating and Evaporative Crystallization of UiO-66 Metal Organic Framework Thin Films

Surface Induced Phenytoin Polymorph. 1. Full Structure Solution by Combining Grazing Incidence X-ray Diffraction and Crystal Structure Prediction

Selective Morphological and Polymorphic Control of CL-20 Thin Films Using Meniscus-Guided Coating

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