Author Archive

Use of a MOP in the production of vanillin

A new method of producing vanillin (3-methoxy-4-hydroxybenzaldehyde) from ferulic acid using a catalytic MOP has been reported.

Vanillin, one of the main chemical components of vanilla, is an important flavouring agent in the food, cosmetic and other industries.  However, although it can be extracted from vanilla pods, less than 1% of the required quantity is obtained in this way.  The remainder is obtained by chemical synthesis using strong oxidising agents and toxic solvents.  Biotechnological production is also possible but there are problems with time-scale, purification and the nature of the bacteria used.   There is, therefore, a demand for cleaner, greener methods of production of vanillin.

This paper reports the production of vanillin in 60% yield from ferulic acid and hydrogen peroxide, when a MOP (metal-organic polyhedron) is used as a catalyst.  Like MOFs (metal-organic frameworks), MOPs are constructed from metal ions and organic ligands but rather than forming frameworks, MOPs are discrete polyhedra. MOFs have been widely studied as potential catalysts but MOPs are practically untried.  Reasons for this include their relative lack of stability and tendency to aggregate.   This paper uses the MOP formed from copper(II) and a ligand from 9H-carbazole-3,6-dicarboxylic acid.  There are also coordinated dimethylformamide and water molecules in the structure.

The catalyst is activated by removing the coordinated solvent molecules by heating.  Ferulic acid and hydrogen peroxide are then reacted in the presence of the MOP.  Best results are obtained when the reaction mixture is sonicated (to reduce possible aggregation of MOP molecules).  A mechanism is proposed starting with coordination of peroxide to the active Cu(II) coordination site (schematically shown above).

The recovered catalyst exhibits a loss of crystallinity and after 5 cycles activity shows a decline.  However, the paper demonstrates the potential for the catalytic use of MOPs for the simple production of vanillin and other compounds.

For more details, read the full paper here:

Synthesis of vanillin via a catalytically active Cu(II)-metal organic polyhedron

Elí Sánchez-González, Alfredo López-Olvera, Olivia Monroy, Julia Aguilar-Pliego, J. Gabriel Flores, Alejandro Islas-Jácome, Mónica A. Rincón-Guevara, Eduardo González-Zamora, Braulio Rodríguez-Molina and Ilich A. Ibarra  
CrystEngComm, 2017, Advance Article
DOI: 10.1039/C6CE02621D, Communication
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Gwenda KydGwenda Kyd has a PhD in metallocarborane chemistry from the University of Edinburgh. Other research work includes the spectroscopic study of the structure of glasses and organometallic electron-transfer reactions and the preparation of new inorganic phosphors. She published a book, ‘Molecules, Medicines and Mischief’, in 2014, on some of the chemicals found in plants and is currently working on a follow-up.

 

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Stability of the anti-histamine drug loratadine

Drugs are often prepared in crystalline form.  However, the relative thermodynamic stability of crystalline compounds can limit water solubility and bioavailability in the body.  An alternative is to make the drugs in an amorphous form that is less stable and more soluble.  Unfortunately, this form tends to revert to the crystalline form during manufacture, processing or storage, which can limit its usefulness.   A new paper by Aiguo Zeng et al., aims to increase understanding of the crystallisation of amorphous drugs, using loratadine (shown below) as a model compound.

Quench-cooling amorphous loratadine

Loratadine is a widely-available, non-sedating anti-histamine, used to treat hay-fever and other allergies.  It has been on the market since 1993 and is included in the World Health Organisation’s Model List of Essential Medicines.

Four amorphous samples were prepared by quench-cooling – where molten compounds are rapidly cooled so they have insufficient time to arrange into a crystal lattice.  Study of the samples obtained by cooling at 298 K, 277 K, 253 K and 233 K showed no significant differences in the crystallisation mechanism with quenching temperature.

However, the tendency to crystallise increased with decreasing quench-cooling temperature.  Authors attribute this to the differences in molecular mobility and relaxation of the samples, especially the so-called Johari-Goldstein process of loratadine, involving motion of all atoms in the molecule. This finding will allow the preparation of  loratadine with a lower tendency to crystallise but which retains the beneficial properties of the amorphous form.   It will also inform studies of the amorphous form of other drug molecules.

For more details, read the full paper at:

Ruimiao Chang, Qiang Fu, Yong Li, Mingchan Wang, Wei Du, Chun Chang and Aiguo Zeng  

CrystEngComm, 2017, Advance Article
DOI: 10.1039/C6CE01645F, Paper
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Gwenda KydGwenda Kyd has a PhD in metallocarborane chemistry from the University of Edinburgh. Other research work includes the spectroscopic study of the structure of glasses and organometallic electron-transfer reactions and the preparation of new inorganic phosphors. She published a book, ‘Molecules, Medicines and Mischief’, in 2014, on some of the chemicals found in plants and is currently working on a follow-up.

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Increasing pore size in metal-organic frameworks

Many potential applications of metal-organic frameworks (MOFs) rely on the size and nature of the available free volume or pores within the framework structure.  These include use for gas storage or capture and catalysis.   Tuning of the pores is typically achieved by variation of the metal ions or organic ligands.  Lengthening the organic chains can lead to increased pore size but is often limited by a decrease in stability of the framework. A new paper by Yan-Zhen Zheng and colleagues at Xi’an Jiaotong University and the University of Arizona reports a new method of structurally modifying MOFs by insertion of alkali metal ions.

In a series of experiments, a heterometallic MOF with O-containing ligands was modified by the insertion of alkali metal ions into the coordination environment formed by two bridged lanthanide centres.  Initially, 2D or 3D Cu-Pr MOFs were formed with bridging isonicotinate ligands, by reacting isonicotinic acid, CuI and Pr(NO3)3 in a range of organic solvents.  The reaction producing one of these MOFs, {[Pr3(Cu4I4)3(ina)9(DMF)4](DMF)}n (where ina is isonicotinato and DMF is N,N-dimethylformamide), was then repeated with the addition of NaCl, KCl, RbCl  or CsCl.

In the NaCl and KCl reactions, new MOFs were produced incorporating Na+ or K+ ions, with void volumes of 53% and 61%, respectively (compared with 10% for the alkali metal ion free MOF).

Reaction involving the next largest ion, Rb+, produced an unstable MOF which could not be studied further.  However, reaction with the larger Cs+ ion produced a new MOF which didn’t contain this ion, but with a void volume of 59%.

The authors suggest that their method of inducing structural variation using appropriately-sized alkali metal ions should be extendable to other ligand systems for the production of a variety of MOFs with novel structures and functions.

For more information, read the full paper at:
An alkali-ion insertion approach to structurally transform metal–organic frameworks
Yue-Qiao Hu, Mu-Qing Li, Teng Li, Yan-Yan Wang, Zhiping Zheng and Yan-Zhen Zheng
CrystEngComm, 2016, Advance Article
DOI: 10.1039/C6CE00540C
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Gwenda KydGwenda Kyd has a PhD in metallocarborane chemistry from the University of Edinburgh. Other research work includes the spectroscopic study of the structure of glasses and organometallic electron-transfer reactions and the preparation of new inorganic phosphors. She published a book, ‘Molecules, Medicines and Mischief’, in 2014, on some of the chemicals found in plants and is currently working on a follow-up.

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Use of nanolimes in conservation

Nanolimes, alcoholic dispersions of colloidal Ca(OH)2 nanoparticles, are commonly used for the conservation of porous materials such as stone and marble.  However, only the basics of the process they undergo – carbonation to produce CaCO3 – are understood and this limits their potential use.

A new paper by Rodriguez-Navarro looks at the carbonation process in detail, with the aims of increasing the effectiveness of and understanding any limitations in the use of nanolimes in conservation.

Conservation of materials using nanolimes is typically carried out in humid air at room temperature.  Under these conditions, amorphous calcium carbonate (ACC) initially forms.  This can then transform into the metastable vaterite (up to 35 wt%) and a small amount of aragonite (up to 5%), but only in the presence of alcohol.  These polymorphs partially dissolve and the stable polymorph, calcite, precipitates.  Alternatively, calcite can form directly after dissolution of ACC.

Nanolime carbonation

Results of the kinetic studies show that the rate-limiting step in the production of calcite is the amount of unreacted Ca(OH)2.  Although the formation of metastable states might be considered a limitation to the use of nanolimes in conservation, the fast kinetics of the vaterite to calcite conversion (72 % in 10 days) means that almost the full consolidation potential can be reached within weeks of application and it is only over very short time-scales that the performance might be sub-optimal.

These results may also have implications for the design of new CaCO3 materials for other applications, using syntheses analogous to the multi-step crystallisation shown in the carbonation of nanolimes in the presence of alcohol.

For more information, read the full paper at:

Amorphous and crystalline calcium carbonate phases during carbonation of nanolimes: implications in heritage conservation

Carlos Rodriguez-Navarro, Kerstin Elert and Radek Ševčík

CrystEngComm, 2016, Advance Article
DOI: 10.1039/C6CE01202G, Paper

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Gwenda Kyd

Gwenda Kyd has a PhD in metallocarborane chemistry from the University of Edinburgh. Other research work includes the spectroscopic study of the structure of glasses and organometallic electron-transfer reactions and the preparation of new inorganic phosphors. She published a book, ‘Molecules, Medicines and Mischief’, in 2014, on some of the chemicals found in plants and is currently working on a follow-up.

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Luminescent MOF detects explosives

A new metal-organic-framework (MOF) based sensor for the explosive, trinitrophenol (TNP or picric acid), is reported by scientists at the Indian Institute of Technology,  Guwahati, India.

MOFs have been studied for a variety of potential uses, including as sensors.  The size and electronic properties of their pores can make MOFs sensitive to particular compounds and these features can be readily modified.  In their paper,  Mostakim SK and Shyam Biswas describe a MOF formed from Zr(IV) and the ligand 4,4′-(benzoijc]ij1,2,5]thiadiazole-4,7-diyl)dibenzoic acid (H2BTDB).  The as-synthesised material, [Zr6O4(OH)4(BTDB)6]·8H2O·6DMF, is activated by stirring with methanol and heating under vacuum, removing water and DMF from the pores. This activated MOF is strongly luminescent both in the solid state and in organic solvents.

Luminescence is quenched in the presence of TNP, an explosive commonly used in the production of fireworks, landmines and matches.  Other uses include: as an antiseptic and to treat burns, in metallurgy and in the dyeing industry. Shock or friction can cause dry TNP to explode so it is usually stored wet for safety reasons.   TNP is also mutagenic and/or carcinogenic and its presence in the environment as a result of industry is problematic.  Current detection methods for TNP and other related explosive compounds have low selectivity and are not portable.

Schematic representation of the selective sensing of TNP

This new MOF not only allows detection of TNP at levels as low as 1.63 × 10−6 M, but is also selective for TNP in the presence of other similar compounds such as trinitrotoluene (TNT). The MOF is also photostable and reusable and therefore has potential for use as a portable TNP sensor in practical situations. The authors are now investigating other potential sensors based on luminescent MOFs using related ligands.

For more information, see the full paper here:

A thiadiazole-functionalized Zr(IV)-based metal–organic framework as a highly fluorescent probe for the selective detection of picric acid
Mostakim SK and Shyam Biswas
CrystEngComm, 2016, Advance Article
DOI: 10.1039/C6CE00421K

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Gwenda KydGwenda Kyd has a PhD in metallocarborane chemistry from the University of Edinburgh. Other research work includes the spectroscopic study of the structure of glasses and organometallic electron-transfer reactions and the preparation of new inorganic phosphors. She has recently published a book on chemicals from plants.

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A new structure-director for formation of C60-fullerenes

The structure-directing properties of 2,4,6-trimethylpyridine (TMP) for the formation of colloidal C60-fullerene are revealed in a new paper by Penterman and Liddell Watson.

C60-fullerenes can support singlet excited states that recombine to produce a red photoluminescence and also have a high refractive index and transparency.  As such, they have a potential use in colloid-based photonic crystals.  Fullerene microcrystals are typically prepared in a solvent-antisolvent system, where the antisolvent promotes nucleation.  The solvent-antisolvent ratio, concentration of fullerene, temperature and mixing conditions can be varied to produce particles with different morphologies. However, there are not many compatible solvent-antisolvent combinations, limiting the nature of the particles that can form.

In this paper, the effect of adding TMP to the tetralin or mesitylene:2-propanol solvent-antisolvent system, is investigated.  When the solvent is tetralin, TMP plays a dominant role in determining the colloid morphology, monodispersity and crystal structure (an SEM of one fullerene solvate produced is shown below).  In the mesitylene  system, the crystals have well-defined faceting, higher aspect ratios and improved packing efficiency.


Graphical abstract: Anisometric C60 fullerene colloids assisted by structure-directing agent

The microcrystals show a reduced fluorescence quantum yield and lifetime, which is thought to be a result of greater fullerene packing efficiency. This is enhanced as the polar TMP additive acts as a blocking agent, adsorbing at the solid–liquid interface and slowing the kinetic rates of growth on certain crystallographic planes. The nucleation period is also shortened, supporting monodispersity.

The use of structure-directing agents could allow the production of fullerene microcrystals with diverse internal crystal structures and external forms.  This may allow the development of fullerenes tuned to possess specific properties, including suitability for use as active building blocks for photonic crystals.  The authors are continuing to explore the potential of this application.

For more details, see the full paper at:

Anisometric C60 fullerene colloids assisted by structure-directing agent

Sonny J. Penterman and Chekesha M. Liddell Watson

CrystEngComm, 2016
DOI: 10.1039/C5CE02122G
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Gwenda KydGwenda Kyd has a PhD in metallocarborane chemistry from the University of Edinburgh. Other research work includes the spectroscopic study of the structure of glasses and organometallic electron-transfer reactions and the preparation of new inorganic phosphors. She has recently published a book on chemicals from plants.
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Understanding gout

A new paper by Lee et al. who carried out research at the National Central University in China, finally explains the formation of gout.  Gout is an inflammatory arthritic condition caused by the deposition of crystals of monosodium urate monohydrate (MSUM) in joints and tendons.  Traditionally associated with over-indulgent consumption of alcohol and rich food, gout was known as the disease of kings.  It has become more common in recent years, affecting 2-3% of the Western population at some point during their lives.

Development of gout is related to raised levels of uric acid in the blood (hyperuricemia).  However, the mechanism of crystallisation of MSUM and the fact that only some people with hyperuricemia develop gout were not understood, but are now unveiled in this new paper.

The morphology of the MSUM formed from uric acid was studied under various Na+ ion concentrations, under conditions mimicking the body (pH 7.4, 37oC).  The formation of a metastable “beachball structure” which converts to “urchin-like aggregates” and “bow-like aggregates” depends on the Na+ ion concentration and it is suggested that the pathogenesis of gout may be related to the transformation of “beachballs” to needles.

When the pH is lowered by adding lactic acid, which would occur during inflammatory response, uric acid dihydrate (UAD) is formed.  As the pH returns to normal, this converts to MSUM, causing an inflammatory response and generating a self-sustaining cycle, as shown in the diagram below.

Formation of gout

The presence of hyaluronate, Na+, K+ and Ca2+ is found to affect the development of gout and a new MSUM “fishtail” morphology was observed in hyaluronate-, Na+– and Ca2+– containing solutions.  A highly water soluble hyaluronate-Ca-urate complex was identified and authors suggest that disruption of this complex would lead to MSUM deposition, causing gout.  Thus, people could have hyperuricemia but not develop gout, if their physiological conditions maintain the complex.

For more information, see the paper at:

The culprit of gout: triggering factors and formation of monosodium urate monohydrate

Meng Hsiu Chih, Hung Lin Lee and Tu Lee

CrystEngComm, 2016, Advance Article
DOI: 10.1039/C5CE01656H, Paper

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Gwenda KydGwenda Kyd has a PhD in metallocarborane chemistry from the University of Edinburgh. Other research work includes the spectroscopic study of the structure of glasses and organometallic electron-transfer reactions and the preparation of new inorganic phosphors. She has recently published a book on chemicals from plants.

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A red-emitting nanophosphor for white LEDs

A new red-emitting nanophosphor with potential use in white light-emitting diodes (LEDs) has recently been reported by Mi and colleagues.

White LEDs are used for lighting as they use little energy, have high brightness and long lifetimes and are considered environmentally friendly. Currently, these LEDs consist of a combination of a yellow-emitting phosphor and a blue LED chip. However, the lack of a red component is problematic, leading to a low colour rendering index (in other words, some colours do not appear naturalistic) and a high colour temperature (giving light a blue hue). Other possible methods of generating white LEDs that use red phosphors are limited by the low stability and efficiency of commercial sulphide-based red phosphors. Now, Mi and colleagues report an efficient and stable europium-based red phosphor that could solve the problem and improve the suitability of white LEDs for certain medical applications.

The phosphor Ca9Eu(PO4)7 was prepared using hydrothermal methods from calcium- and europium- nitrates and phosphoric acid. It shows a red emission at 616nm under excitation at 397nm. This is attributed to the 5D07F2 transition in Eu3+, which will only happen when the Eu ion occurs in sites without inversion symmetry (as it is parity forbidden).

morphology of the nanophosphor Ca9Eu(PO4)7

When the phosphor was doped (in other words, when Eu was partially replaced by Gd, La or Y), the emission intensity decreased. The pH value of the synthesis reaction was found to alter the morphology of the phosphor (see the diagram below) from rods to spheres, which had different luminescence properties. The most favourable properties were obtained from rods obtained at pH 7, attributed to the smallest number of lattice defects being formed at this pH. The rods are approximately 100nm long with an aspect ratio (long axis length to width ratio) of 2.5. This phosphor shows a good colour saturation index (R = 2.4) and future studies to optimise its properties could lead to potential application in white LEDs.

For more details read the full paper at:

Hydrothermal synthesis and photoluminescence properties of Ca9Eu(PO4)7 nanophosphors
Jiacheng Sun, Xiaoyun Mi, Lijian Lei, Xiaoying Pan, Shuyi Chen, Zan Wang, Zhaohui Bai and Xiyan Zhang
CrystEngComm, 2015
DOI: 10.1039/C5CE01289A

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Gwenda KydGwenda Kyd has a PhD in metallocarborane chemistry from the University of Edinburgh. Other research work includes the spectroscopic study of the structure of glasses and organometallic electron-transfer reactions and the preparation of new inorganic phosphors. She has recently published a book on chemicals from plants.

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New probes for detecting the pesticide thiram by SERS

Highly selective and sensitive surface enhanced Raman spectroscopy (SERS) probes for the pesticide thiram have recently been reported by Zou and Wang et al.

SERS can provide low-cost, non-destructive, fast detection of potential environmental pollutants such as thiram.   This sulfur-containing pesticide and fungicide is commonly used to protect orchard fruits and soya but is toxic to humans both in acute doses and by long-term exposure to smaller quantities.

An effective SERS substrate has a rough metal surface – typically made of noble metals such as Ag – which adsorbs the molecules of interest.  The surface is coated on a glass or a core metal oxide particle, such as Fe3O4.   After oleate-modified Ag microspheres were found to possess selective thiram detection by surface-ligand exchange, attempts were made to generate Ag composite microspheres with oleate modifications, using a gel system.  However, the dumb-bell shaped particles produced showed a poor SERS performance, due to the lack of so-called hot-spots – areas where surface enhancement is intense.

In the new paper, the successful preparation of oleate-modified silver composite microspheres with dense hot-spots is demonstrated.  The Fe3O4 microspheres, capped with polyacrylate groups are prepared by a solvothermal method.  The carboxylate groups interact with Ag ions which are subsequently reduced using sodium borohydrate.  The surface Ag particles seed further coating by Ag in the presence of oleate in a gel system (see diagram below), completely covering the Fe3O4 microsphere in oleate-modified Ag nanoparticles.

Gel method for producing SERS probe for thiram

The spherical particles produced show SERS detection of thiram at trace amounts, with the thiram spectrum detected at a concentration as low as 1 x 10−8 M.  Under the same conditions, two other common pesticides, methyl parathion and trichorfon, show no SERS signals. The results suggest that the system could potentially be used for the selective detection of traces of thiram in solution.

For more details, see the full paper at:

Gel-assisted synthesis of oleate-modified Fe3O4@Ag composite microspheres as magnetic SERS probe for thiram detection
Haihong Zheng, Bingfang Zou, Lin Chen, Yongqiang Wang, Xiaoli Zhang and Shaomin Zhou
CrystEngComm, 2015, Advance Article
DOI: 10.1039/C5CE01017A

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Gwenda KydGwenda Kyd has a PhD in metallocarborane chemistry from the University of Edinburgh. Other research work includes the spectroscopic study of the structure of glasses and organometallic electron-transfer reactions and the preparation of new inorganic phosphors. She has recently published a book on chemicals from plants.

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Sensing hazardous gases using tungsten trioxide microflowers

A facile new preparation of shape-controlled tungsten trioxide (WO3) sensors is reported in a recent paper by Zhang et al.  These sensors show good selectivity towards the hazardous gas hydrogen sulfide (H2S) at a relatively low operating temperature.

Detection of hazardous gases is necessary to monitor environmental pollution and ensure levels do not exceed legally permitted limits.  In the case of H2S, the general industry ceiling limit is 20 ppm.  At concentrations of above 50 ppm, eye damage is likely and at higher concentrations (above 320 ppm) pulmonary oedema and breathing problems resulting in death can occur.  There is, therefore, a demand for cheap, reliable and selective sensors for identifying low concentrations of H2S.

Metal-oxide semiconductors such as WO3 are attractive potential sensors which are relatively cheap and easy to fabricate.  As the sensing ability of the particles depends on their morphology, the preparation of shape-controlled particles is a requirement.  Zhang et al achieve this by reacting sodium tungstate and potassium sulfate in an acidic environment.  Adding oxalic acid and heating at 100oC then calcining the resulting product produces WO3 microflowers, of diameter 16 μm. Study of the reaction shows it can be divided into four processes.  Crucially, during the final stage, needle-like nanosheets grow radially from central particles to produce a flower-like morphology (see the scheme below).

Tungsten trioxide sensors for hazardous gases

These particles have excellent potential for application as H2S sensors – at 160oC they show high sensitivity and sensor response along with good repeatability and selectivity towards H2S.  The high performance of WO3 microflowers is related to their structure.  They are assembled from nanosheets composed of several nanowhiskers in parallel, giving highly exposed surfaces and so more pathways for gas absorption and electron exchange.  The nanosheets are homogeneous and single-crystalline so electron transport can occur between particles without overcoming boundary barriers which would decrease the sensitivity.

For more details, read the full paper at:

Low-temperature solvothermal synthesis of hierarchical flower-like WO3nanostructures and their sensing properties for H2S
Bingxin Xiao, Qi Zhao, Chuanhai Xiao, Tianye Yang, Pan Wang, Fei Wang, Xiaodong Chen and Mingzhe Zhang
CrystEngComm, 2015
DOI: 10.1039/C5CE00870K

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Gwenda KydGwenda Kyd has a PhD in metallocarborane chemistry from the University of Edinburgh. Other research work includes the spectroscopic study of the structure of glasses and organometallic electron-transfer reactions and the preparation of new inorganic phosphors. She has recently published a book on chemicals from plants.

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