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DOE OSTI2015

Removing chiral contamination of lactate solutions by selective metabolism of the D-enantiomer

A bio-based process is appealing for purification of L-lactic acid, the major enantiomer of polylactic acid syrup, generated by thermochemical processes at the end of life of PLA-based plastics, from its chiral impurity, d-lactic acid, before reuse. Polylactic acid (PLA), a renewable alternative to petroleum-derived plastics, contains a mixture of l- and d-lactic acid (LA) isomers with the l-isomer dominating (up to 95 %). A novel bio-based process was developed to produce chirally pure l-LA from syrup produced during recycling of PLA-plastics. This process utilizes an engineered Escherichia coli (strain DC1001) containing novel gene deletions (lld, ykg) that eliminated the oxidative metabolism of L-lactate, leaving the membrane-bound d-lactate dehydrogenases to selectively metabolize the d-isomer. Strain DC1001 removed 8.7 g d-lactate l –1 from a PLA-syrup containing 135 g total lactic acid l –1 in 24 h. Average rates of removal of D-lactic acid were 0.25 g D-lactate h –1 (g cell dry weight) –1 and 0.36 g D-lactate l –1 h –1 . Bio-based purification of PLA-syrup utilizing E. coli strain DC1001 is an attractive process step during recycling of PLA-plastics. Here, this selective oxidation process can also be used to remove chiral contamination of L-lactate in medical applications.

59 BASIC BIOLOGICAL SCIENCES↗

DOE OSTI2021

Prebiotic properties of Bacillus coagulans MA-13: production of galactoside hydrolyzing enzymes and characterization of the transglycosylation properties of a GH42 β-galactosidase

The spore-forming lactic acid bacterium Bacillus coagulans MA-13 has been isolated from canned beans manufacturing and successfully employed for the sustainable production of lactic acid from lignocellulosic biomass. Among lactic acid bacteria, B. coagulans strains are generally recognized as safe (GRAS) for human consumption. Low-cost microbial production of industrially valuable products such as lactic acid and various enzymes devoted to the hydrolysis of oligosaccharides and lactose, is of great importance to the food industry. Specifically, α- and β-galactosidases are attractive for their ability to hydrolyze not-digestible galactosides present in the food matrix as well as in the human gastrointestinal tract. In this work we have explored the potential of B. coagulans MA-13 as a source of metabolites and enzymes to improve the digestibility and the nutritional value of food. A combination of mass spectrometry analysis with conventional biochemical approaches has been employed to unveil the intra- and extra- cellular glycosyl hydrolase (GH) repertoire of B. coagulans MA-13 under diverse growth conditions. The highest enzymatic activity was detected on β-1,4 and α-1,6-glycosidic linkages and the enzymes responsible for these activities were unambiguously identified as β-galactosidase (GH42) and α-galactosidase (GH36), respectively. Whilst the former has been found only in the cytosol, the latter is localized also extracellularly. The export of this enzyme may occur through a not yet identified secretion mechanism, since a typical signal peptide is missing in the α-galactosidase sequence. A full biochemical characterization of the recombinant β-galactosidase has been carried out and the ability of this enzyme to perform homo- and hetero-condensation reactions to produce galacto-oligosaccharides, has been demonstrated. Probiotics which are safe for human use and are capable of producing high levels of both α-galactosidase and β-galactosidase are of great importance to the food industry. In this work we have proven the ability of B. coagulans MA-13 to over-produce these two enzymes thus paving the way for its potential use in treatment of gastrointestinal diseases.

59 BASIC BIOLOGICAL SCIENCES↗

DOE OSTI2023

Muconic acid production from algae hydrolysate as a high-value co-product of an algae biorefinery

Muconic acid is an attractive bio-derived product because it can be easily converted to adipic acid, a high-value and high-volume monomer used in the production of nylon and other valuable consumer plastics. As such, production of muconic acid from algae hydrolysate was explored to expand the suite of products available from algal biomass. Here we have established initial performance parameters and have shown that the range of substrates present in algae hydrolysate that are consumed by Pseudomonas putida includes at least glucose, mannose, glycerol, acetic acid, and lactic acid. We achieved complete utilization of these major carbon sources found in Scenedesmus acutus hydrolysate with a maximum muconic acid productivity of 0.25 g/L h. Final titer was 13.0 g/L (27% molar process yield) at approximately 50 h. In addition, algae hydrolysate does not require any additional nutrients to achieve these performance metrics. Techno-economic analysis showed the potential to support up to 150 algal biorefineries at this yield with significant greenhouse gas reductions.

09 BIOMASS FUELS↗

DOE OSTI2013

Aqueous phase catalytic conversion of agarose to 5-hydroxymethylfurfural by metal chlorides

Abstract: 5-HMF is a key intermediate for producing chemicals and fuels that can substitute for today’s petroleum-derived feedstocks. A series of metal chlorides, including NaCl, CaCl2, MgCl2, ZnCl2, CuCl2, FeCl3, and CrCl3, were comparatively investigated to catalyze agarose degradation for production of 5-HMF at temperature 180 oC, 200 oC, and 220 oC for 30 min, with catalyst concentration of 0.5% (w/w), 1% (w/w) and 5% (w/w), and substrate concentration of 2% (w/w). Our results revealed that alkali metal chlorides and alkali earth metal chlorides such as NaCl, CaCl2 and MgCl2 gave better 5-HMF yield compared with transition metal chlorides including ZnCl2, CrCl3, CuCl2 and FeCl3. 1% (w/w) MgCl2 was the more favorable catalyst for 5-HMF production from agarose, and resulted in 40.7% 5-HMF yield but no levulinic acid or lactic acid at 200 oC, 35 min. The reaction pathways of agarose degradation catalyzed by MgCl2 were also discussed.

The highest 5-HMF yield was 40.7% at 200 °C and 35↗

DOE OSTI2020

Advances in catalytic production processes of biomass-derived vinyl monomers

Plastic industries currently source the majority of monomers from crude oil substances. Although we have witnessed a significant interest of companies in the utilization of sustainable feedstock materials for bio-based compound synthesis in the past decade, the transition to photosynthetic or chemosynthetic plant-based production in a circular carbon economy is largely slow due to complex biomass processing, costs and related reaction factors. The upgrade of the separated platform chemicals with a deeper supporting understanding of processes, models and a root–cause analysis about the underlying distribution challenges of engineered transformation mechanisms, catalyzed conversion pathways and selectivity would be beneficial to advance applied scientific development, bio-refining and manufacturing output amount. This review provides a summary, assessment and perspective for three important polymer-forming vinyl molecules, i.e. acrylic acid, methacrylic acid and styrene. These provide a backbone to produce acrylates, polystyrene, resins, rubbers, protective surface coatings, adhesives, textiles and other obtained copolymers. A succinct analytical overview on the thermo-catalytic intermediate routes for property-wise drop-in alternatives is presented. Sugars, acrolein, allyl alcohol, ethylbenzene, glycerol, 3-hydroxypropionic acid, isobutene, itaconic acid and lactic acid are considered as the main starting reactants. Catalysts span mixed metal oxides, silicates, native or impregnated zeolite frameworks (HBEA, HZSM, and MFI) and hetero-poly acids as well as homogeneous base hydroxides or platinum group metals, supported on carbon, alumina and sulfates. Finally, the article concludes with a brief state sum-up of the results, topics and opportunities for systematic future research or scaling.

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CH↗

DOE OSTI2012

Recombinant microorganisms for increased production of organic acids

Disclosed are recombinant microorganisms for producing organic acids. The recombinant microorganisms express a polypeptide that has the enzymatic activity of an enzyme that is utilized in the pentose phosphate cycle. The recombinant microorganism may include recombinant Actinobacillus succinogenes that has been transformed to express a Zwischenferment (Zwf) gene. The recombinant microorganisms may be useful in fermentation processes for producing organic acids such as succinic acid and lactic acid. Also disclosed are novel plasmids that are useful for transforming microorganisms to produce recombinant microorganisms that express enzymes such as Zwf.

60 APPLIED LIFE SCIENCES↗

DOE OSTI2013

Recombinant microorganisms for increased production of organic acids

59 BASIC BIOLOGICAL SCIENCES↗

DOE OSTI2023

Trophic interactions shape the spatial organization of medium-chain carboxylic acid producing granular biofilm communities

Abstract Granular biofilms producing medium-chain carboxylic acids (MCCA) from carbohydrate-rich industrial feedstocks harbor highly streamlined communities converting sugars to MCCA either directly or via lactic acid as intermediate. We investigated the spatial organization and growth activity patterns of MCCA producing granular biofilms grown on an industrial side stream to test (i) whether key functional guilds (lactic acid producing Olsenella and MCCA producing Oscillospiraceae) stratified in the biofilm based on substrate usage, and (ii) whether spatial patterns of growth activity shaped the unique, lenticular morphology of these biofilms. First, three novel isolates (one Olsenella and two Oscillospiraceae species) representing over half of the granular biofilm community were obtained and used to develop FISH probes, revealing that key functional guilds were not stratified. Instead, the outer 150–500 µm of the granular biofilm consisted of a well-mixed community of Olsenella and Oscillospiraceae, while deeper layers were made up of other bacteria with lower activities. Second, nanoSIMS analysis of 15N incorporation in biofilms grown in normal and lactic acid amended conditions suggested Oscillospiraceae switched from sugars to lactic acid as substrate. This suggests competitive-cooperative interactions may govern the spatial organization of these biofilms, and suggests that optimizing biofilm size may be a suitable process engineering strategy. Third, growth activities were similar in the polar and equatorial biofilm peripheries, leaving the mechanism behind the lenticular biofilm morphology unexplained. Physical processes (e.g., shear hydrodynamics, biofilm life cycles) may have contributed to lenticular biofilm development. Together, this study develops an ecological framework of MCCA-producing granular biofilms that informs bioprocess development.

09 BIOMASS FUELS↗

DOE OSTI2016

A pair of novel Cd(II) enantiomers based on lactate derivatives: Synthesis, crystal structures and properties

A pair of novel 3D homochiral metal−organic frameworks (HMOFs), namely [Cd{sub 2.5}((R)-CIA){sub 6}(1,4-DIB)(H{sub 2}O){sub 2}]·((CH{sub 3}){sub 2}NH{sub 2})·H{sub 2}O (1-D), [Cd{sub 2.5}((S)-CIA){sub 6}(1,4-DIB)(H{sub 2}O){sub 2}]·((CH{sub 3}){sub 2}NH{sub 2})·H{sub 2}O (1-L), have been synthesized using lactic acid derivative ligands ((R)-H{sub 3}CIA and (S)-H{sub 3}CIA) and 1,4-DIB. Crystallographic analyses indicate that the complexes 1-D and 1-L are packed by cage substructures. Some physical characteristics, such as solid-state circular dichroism (CD), thermal stabilities and photoluminescent properties are also investigated. Our results highlight the effective method to apply lactic acid derivative ligands to form interesting HMOFs. - Graphical abstract: Using lactic acid derivative ligands ((R)-H{sub 3}CIA and (S)-H{sub 3}CIA) and 1,4-DIB to assemble with Cd{sup 2+} ions, a pair of novel 3D homochiral metal-organic frameworks (HMOFs) with cage substructures have been synthesized. Display Omitted - Highlights: • Lactic acid derivative ligands • Cage substructure • Enantiomers.

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CH↗

DOE OSTI2023

Wetlands harbor lactic acid-driven chain elongators

Wetlands are globally significant carbon storage hotspots. Recent research has suggested that microbially derived metabolites may contribute to soil organic matter formation. Identifying pathways driving the formation of such metabolites is critical to understand the global impact of wetland carbon cycling. Here, we evaluate the presence of chain-elongating organisms converting two to three carbon compounds (i.e., lactic and acetic acid) to medium-chain carboxylic acids (MCCA; i.e., six-carbon caproic acid) in wetland soils. We demonstrate the enrichment of a lactic acid-driven chain-elongating community from wetland soils producing a mixture of butyric and caproic acid. The enriched community was dominated by Clostridiaceae, Ruminococcaceae, and Lachnospiraceae, three families with known chain elongators. Amplicon sequencing identified three Ruminococcaceae and one Clostridiaceae zero-radius OTU (zOTU) that were (i) present in the soil, (ii) enriched over 1% relative abundance in the bioreactor, and (iii) were closely related to known chain elongators. Moreover, close relatives of the three Ruminococcaceae zOTU were also observed in several other wetland microbiomes. From this observation, we conclude that close relatives of known chain elongators, potentially capable of lactic acid-driven MCCA production themselves, are present in wetland soils. This observation may have implications for our understanding of carbon cycling and storage in wetland ecosystems.

59 BASIC BIOLOGICAL SCIENCES↗

DOE OSTI2022

Scaling up carboxylic acid production from cheese whey and brewery wastewater via methane-arrested anaerobic digestion

In a circular economy, organic waste streams are valuable resources for sustainably producing chemicals and fuels. This study investigates a new methane-arrested anaerobic digestion (MAAD) process that converts high-strength cheese whey and brewery wastewater into carboxylic acids. The process was developed and optimized under various bench-scale semi-continuous (fed-batch) operating conditions (e.g., retention time, organic loading rate, pH, and feed/harvest frequency). The MAAD responses to various control-failure scenarios were also systematically investigated. The highest total acid productivity was 26g/(L liq ·d) with a substrate conversion of 0.79g COD digested /g COD fed at a hydraulic retention time (HRT) of approximately 2 d in a 14-L digester. The most stable conditions for digester operation (HRT 3 d at pH 6.0 and 40°C) were selected for process scale-up to 100gal (~380 L). Semi-continuous, pilot-scale MAAD successfully produced a total acid concentration of 40.6+/-1.1 g/L with 8.1% acetic acid, 45.1% butyric acid, and 44.5% lactic acid. The links between wastewater characteristics, operation mode, digester scale, and microbial community structure were statistically analyzed. The results show genera Sporolactobacillus and Clostridium positively correlate with butyric acid production (Pearson correlation coefficient>0.5). Moreover, four kinetic models were developed and fit to batch MAAD experimental datasets (R 2 >95%) and were successfully applied to predict the total acid production in both bench-and pilot-scale semi-continuous MAADs. In conclusion, this study shows MAAD has the potential for industrial-scale applications and is a robust platform to valorize low- or negative-value waste streams into high-value bioproducts.

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CH↗

DOE OSTI2022

Enhancing organic matter removal, product recovery, and hydrogen generation from fermentation wastewater

Existing ethanol biorefineries produce billions of gallons of wastewater (stillage) that must be treated extensively prior to discharge or concentrated in an energy intense evaporation step to produce animal feed as a value-added bioproduct. Yeasts and filamentous fungi were screened for growth and reduction of soluble organic compounds, carbohydrates, and protein from stillage to identify species capable of rapidly concentrating organic compounds into readily separable biomass in an attempt to concentrate the product using a much more efficient centrifugation step. Yeasts amenable to production of biomass derived products including bio-oils (Yarrowia lipolytica and Rhodotorula pallida), chitosan (Aspergillus niger) and animal feed (Cyberlindnera jadinii) were identified as well as microbes capable of efficient production of small organic acids with applications as bioderived polymers including 3-hydroxypropionic acid (engineered A. niger) and lactic acid using a co-culture of Debaryomyces udenii and Lactobacillus pentosus. The filamentous fungus A. niger eliminated all specifically measured soluble organics (glycerol, acetate, lactate, ethanol, and citrate) in under 48 hours and reduced total soluble protein content by 46% and total carbohydrate content by 83% within 96 hours, the greatest reduction in organic content observed. During this process an A. niger strain engineered to produce 3-hydroxypropionic acid achieved a yield of 0.35 C-mol 3HP / C-mol non-protein organics consumed at an overall rate of 0.09 g/Lh in unmodified stillage without pH control. Stillage treated by the fodder yeast C. jadinii as well as stillage containing acetic or lactic acid was found to be most suitable for growth by electrogenic bacteria with applications in production of electricity or hydrogen from wastewater. This work establishes fungal and bacterial strains appropriate for biological treatment of stillage to produce biomass derived products, soluble commodity chemicals, energy, and treated water to reduce the energy intensity and improve the economics of ethanol biorefineries.

09 BIOMASS FUELS↗

DOE OSTI2024

Process strategies for recovery of sugars, lipids, and lignin from oilcane bagasse using natural deep eutectic solvents (NADES)

Sugarcane is being enhanced as a bioenergy crop by engineering it to accumulate and store lipids along with polymeric sugars in vegetative tissues. However, there is no existing process that allows for processing this new crop to recover both lipid and cellulosic sugars from the oilcane bagasse. Therefore, a comprehensive investi- gation of two pretreatment methods—natural deep eutectic solvents (NADES) and chemical-free hydrothermal pretreatment (HT) was conducted to judge their suitability for recovering fermentable sugars, lipids, and lignin from bagasse. Two NADES, i.e., choline chloride: lactic acid (ChCl:LA) and betaine: lactic acid (BT:LA) were prepared using a 1:2 M ratio and were evaluated for pretreatment of oilcane bagasse at 10, 20, and 50 % (w/w) solids, followed by enzymatic hydrolysis at 10 % (w/w) solids. Notably, ChCl:LA NADES treatment at 10 % (w/ w) solids at 140 °C for 2 h, solubilized 78.8 % of lignin and 80.4 % of hemicellulose and allowed 82.7 % enzymatic conversion of glucans to glucose. In contrast, HT pretreatment removed approximately 87.6 % of the hemicellulose and provided an enzymatic glucose yield of 69.7 %. Furthermore, ChCl:LA operated at 50 % solids loading the enriched lipids 2.6-fold (9.2 wt%) in recovered solids compared to HT (6.4 %) and BT:LA (5.1 %) pretreatment processes. NMR-HSQC and GPC analysis showed that ChCl:LA also cleaved the most lignin β–O–4 linkages and demonstrated lower molecular weight compared to HT. As a result, this study demonstrates that NADES pretreatment is an effective green processing method for recovering lipids, sugars, and lignin from bioenergy crops at high solid loading (50 % w/w) within the context of an integrated biorefinery.

09 BIOMASS FUELS↗

DOE OSTI2024

Data for Process Strategies for Recovery of Sugars, Lipids, and Lignin from Oilcane Bagasse Using Natural Deep Eutectic Solvents (NADES)

Sugarcane is being enhanced as a bioenergy crop by engineering it to accumulate and store lipids along with polymeric sugars in vegetative tissues. However, there is no existing process that allows for processing this new crop to recover both lipid and cellulosic sugars from the oilcane bagasse. Therefore, a comprehensive investigation of two pretreatment methods—natural deep eutectic solvents (NADES) and chemical-free hydrothermal pretreatment (HT) was conducted to judge their suitability for recovering fermentable sugars, lipids, and lignin from bagasse. Two NADES, i.e., choline chloride: lactic acid (ChCl:LA) and betaine: lactic acid (BT:LA) were prepared using a 1:2 M ratio and were evaluated for pretreatment of oilcane bagasse at 10, 20, and 50 % (w/w) solids, followed by enzymatic hydrolysis at 10 % (w/w) solids. Notably, ChCl:LA NADES treatment at 10 % (w/w) solids at 140 °C for 2 h, solubilized 78.8 % of lignin and 80.4 % of hemicellulose and allowed 82.7 % enzymatic conversion of glucans to glucose. In contrast, HT pretreatment removed approximately 87.6 % of the hemicellulose and provided an enzymatic glucose yield of 69.7 %. Furthermore, ChCl:LA operated at 50 % solids loading the enriched lipids 2.6-fold (9.2 wt%) in recovered solids compared to HT (6.4 %) and BT:LA (5.1 %) pretreatment processes. NMR-HSQC and GPC analysis showed that ChCl:LA also cleaved the most lignin β–O–4 linkages and demonstrated lower molecular weight compared to HT. This study demonstrates that NADES pretreatment is an effective green processing method for recovering lipids, sugars, and lignin from bioenergy crops at high solid loading (50 % w/w) within the context of an integrated biorefinery.

Conversion↗

DOE OSTI2019

Fluctuant storage temperature increased the heterogeneous distributions of pH and fermentation products in large round bale silage

Abstract In practical of silage production, variations in the fermentation parameters of silage might be attributable to changes in weather data, especially for ambient temperature. The objective of this study was to investigate how the changed temperature of outside weather condition affects distributions of pH and fermentation products in large round bale silage. The bale silages (1.22 m × 1.25 m ø; density, about 168.9 kg dry matter [DM]/m 3 ) were produced by BR6090 Combi from New Holland Agriculture, wrapped with six layers of stretch film, stored at ambient temperature (2–20°C) and constant temperature (10°C; 15°C; 25°C) for 3, 9, 15, 45 and 90 days. Compared with other silages, silage stored at 25°C had higher ( p < 0.05) lactic acid content, lower ( p < 0.05) pH, butyric acid content and ammonia‐nitrogen (N) ratio of total N. Fluctuant storage temperature limited lactic acid fermentation process with delayed pH decline and continuous butyric production and crude protein (CP) degradation. The differences of pH, lactic acid, propionic acid and ammonia‐N were considerably less evident in the centre of silages stored at different temperatures, and they increased towards the boundaries. The data shows that fluctuant storage temperature had undesirable effect on the fermentation quality of silage, especially for the external part of silo; relatively high and stable storage temperature for initial stage of ensiling process was necessary, but did not promote a positive response to the homogeneous distributions of pH and fermentation products in large round bale silage.

Li, Ping↗

DOE OSTI2021

Diverse Profile of Fermentation Byproducts From Thin Stillage

The economy of biorefineries is influenced not only by biofuel production from carbohydrates but also by the production of valuable compounds from largely underutilized industrial residues. Currently, the demand for many chemicals that could be made in a biorefinery, such as succinic acid (SA), medium-chain fatty acids (MCFAs), and lactic acid (LA), is fulfilled using petroleum, palm oil, or pure carbohydrates as raw materials, respectively. Thin stillage (TS), the residual liquid material following distillation of ethanol, is an underutilized coproduct from the starch biofuel industry. This carbon-rich material has the potential for chemical upgrading by microorganisms. Here, we explored the formation of different fermentation products by microbial communities grown on TS using different bioreactor conditions. At the baseline operational condition (6-day retention time, pH 5.5, 35°C), we observed a mixture of MCFAs as the principal fermentation products. Operation of a bioreactor with a 1-day retention time induced an increase in SA production, and a temperature increase to 55°C resulted in the accumulation of lactic and propionic acids. In addition, a reactor operated with a 1-day retention time at 55°C conditions resulted in LA accumulation as the main fermentation product. The prominent members of the microbial community in each reactor were assessed by 16S rRNA gene amplicon sequencing and phylogenetic analysis. Under all operating conditions, members of the Lactobacillaceae family within Firmicutes and the Acetobacteraceae family within Proteobacteria were ubiquitous. Members of the Prevotellaceae family within Bacteroidetes and Lachnospiraceae family within the Clostridiales order of Firmicutes were mostly abundant at 35°C and not abundant in the microbial communities of the TS reactors incubated at 55°C. The ability to adjust bioreactor operating conditions to select for microbial communities with different fermentation product profiles offers new strategies to explore and compare potentially valuable fermentation products from TS and allows industries the flexibility to adapt and switch chemical production based on market prices and demands.

59 BASIC BIOLOGICAL SCIENCES↗

DOE OSTI2021

Effect of stereochemistry on nanoscale assembly of ABA triblock copolymers with crystallizable blocks

We report on the nanoscale assembly of poly(lactic acid)-b-poly(ethylene oxide)-b-poly(lactic acid) (PLA-PEO-PLA) triblock copolymers in water, focusing on the effect of stereochemistry, where the PLA blocks are statistical copolymers of l-lactide and d-lactide with l/d ratios of 100/0, 95/5, 90/10, 85/15, 75/25, and 50/50. Small-angle neutron scattering (SANS) shows a nearly constant d-spacing as concentration varies in triblock systems with l/d ratios of 90/10 and 95/5, which we attribute to inhomogeneity in the structure of these gels, supported by previous USANS and confocal microscopy studies. The SANS data fit well to a core-shell ellipsoid form factor model with a hard-sphere structure factor. Polymeric micelles with l/d ratios from 75/25 to 85/15 displayed very high aggregation numbers, consistent with a strong interaction between PLA chains and the enhanced storage modulus observed in rheological studies of these systems. While the 90/10 and 95/5 samples showed lower aggregation numbers, their SANS profiles shows close spacing between micelles, which may promote a high fraction of intermicellar bridging chains, also consistent with a higher storage modulus. Overall, these results provide insight into the micellar assembly behavior of block copolymers with a crystallizable block, and indicate that tuning stereochemistry of PLA-based block copolymers is an effective means of modifying micellar properties for specific applications.

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CH↗

DOE OSTI2017

Homochiral coordination polymers with helixes and metal clusters based on lactate derivatives

Utilizing the lactic acid derivatives (R)-4-(1-carboxyethoxy)benzoic acid (denoted: (R)-H{sub 2}CBA) and (S)-4-(1-carboxyethoxy)benzoic acid (denoted: (S)-H{sub 2}CBA)as chiral linkers to self-assemble with 4, 4′-bipyridine (denoted: BIP) and Cd(II) ions, a couple of three-dimensional homochiral coordination polymers, namely [Cd{sub 3}((R)-CBA){sub 3} (BIP){sub 2}(H{sub 2}O)]·xGuest (1-D) and [Cd{sub 3}((S)-CBA){sub 3}(BIP){sub 2}(H{sub 2}O)]·xGuest (1-L), have been synthesized under solvothermal reaction condition. Single crystal X-ray diffraction analysis reveals the two complexes contain single helical chains based on enantiopure ligands and cadmium clusters. Moreover, some physical characteristics such as PXRD, thermal stability, solid-state circular dichroism (CD) and luminescent were also investigated. - Graphical abstract: Utilizing enantiomeric lactic acid derivatives (R)-H{sub 2}CBA and (S)-H{sub 2}CBA to assemble with Cd{sup 2+} ions and ancillary BIP ligands, a couple of 3D homochiral coordination polymers with metal clusters and helical chains have been prepared by hydrothermal reaction. - Highlights: • Chiral lactic acid derivative. • Enantiomeric coordination polymer. • Helical chain. • Trinuclear cadmium cluster.

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CH↗