A combined gas-phase dissociative ionization, dissociative electron attachment and deposition study on the potential FEBID precursor [Au(CH₃)₂Cl]₂

• Elif Bilgilisoy,
• Ali Kamali,
• Thomas Xaver Gentner,
• Gerd Ballmann,
• Sjoerd Harder,
• Hans-Peter Steinrück,
• Hubertus Marbach and
• Oddur Ingólfsson

Beilstein J. Nanotechnol. 2023, 14, 1178–1199, doi:10.3762/bjnano.14.98

Facile preparation of Au- and BODIPY-grafted lipid nanoparticles for synergized photothermal therapy

• Yuran Wang,
• Xudong Li,
• Haijun Chen and
• Yu Gao

Beilstein J. Nanotechnol. 2022, 13, 1432–1444, doi:10.3762/bjnano.13.118

• measured on a Bruker AVANCE 400 spectrometer (400 MHz). The synthesis of BDP is shown in Scheme 2. BDP1 was synthesized in accordance with a previous report [18]. 1H NMR (500 MHz, CDCl3) δ 7.15 (d, J = 5.4 Hz, 2H), 6.99 (d, J = 6.5 Hz, 2H), 5.96 (s, 2H), 3.86 (s, 3H), 2.54 (s, 6H), 1.42 (s, 6H); 13C NMR

• (150 MHz, DMSO-d6) δ 160.3, 155.1, 143.2, 142.6, 131.6, 129.6, 126.4, 121.7, 115.1, 55.7, 14.7; HRESIMS m/z: [M + H]+ calcd, 355.1788; found, 355.1791. BDP2 was prepared as reported in a previously reported work [19]. 1H NMR (400 MHz, CDCl3) δ 7.16 (d, J = 8.6 Hz, 2H), 7.06 (d, J = 8.6 Hz, 2H), 3.92 (s

• over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to afford the crude product. The crude product was purified via silica gel column chromatography using DCM/PE = 1:1 as eluent to obtain a green solid. 1H NMR (500 MHz, CDCl3) δ 8.06 (d, J = 16.5 Hz, 2H), 7.54 (d, J = 8.7 Hz, 4H

Supramolecular assembly of pentamidine and polymeric cyclodextrin bimetallic core–shell nanoarchitectures

• Alexandru-Milentie Hada,
• Nina Burduja,
• Marco Abbate,
• Claudio Stagno,
• Guy Caljon,
• Louis Maes,
• Nicola Micale,
• Massimiliano Cordaro,
• Angela Scala,
• Antonino Mazzaglia and
• Anna Piperno

Beilstein J. Nanotechnol. 2022, 13, 1361–1369, doi:10.3762/bjnano.13.112

• redispersed in deuterium oxide to perform NMR analyses. The 1H NMR spectra of PolyCD, nanoG, and nanoGS provided only limited structural information due to the complex structure of PolyCD and/or its eventual oxidated derivatives. The pattern of resonances attributed to the β-CD-branched polymer was very

• metallic Au NPs, the new diagnostic resonance at 8.30 ppm was detected in 1H NMR spectra of nanoG (Figure 3A, green trace). According to the literature, this signal suggests the formation of formic acid as a decomposition product during the gold reduction process in the carbohydrate/Au(III) system [25]. To

• pentamidine and Au@Ag/PolyCD (nanoGSP). (A) UV–vis spectra of nanoG and nanoGS (red line: freshly prepared nanoGS; blue line: 4 times diluted nanoGS; d = 1 cm for nanoG and d = 0.2 cm for nanoGS). (B,C) TEM images of nanoG and nanoGS, respectively. Scale bar is 5 nm. (A) 1H-NMR spectra of PolyCD, nanoG, and

Design of surface nanostructures for chirality sensing based on quartz crystal microbalance

• Yinglin Ma,
• Xiangyun Xiao and
• Qingmin Ji

Beilstein J. Nanotechnol. 2022, 13, 1201–1219, doi:10.3762/bjnano.13.100

• outstanding sensing properties, with real-time, sensitive and selective chiral detection, high durability, and easy recovery. To understand the chiral recognition between calixarenes and analytes, Zoya I. Kazantseva et al. combined QCM and proton magnetic resonance spectroscopy (1H NMR) techniques to study

• promoted the combination of S-1-phenethylamine, while the ortho-position may combine with R-1-phenethylamine. The QCM results were consistent with the data from 1H NMR spectroscopy. Moreover, the QCM method may also allow for the detection of weak interactions of amides and esters with amines and a slight

Recent advances in green carbon dots (2015–2022): synthesis, metal ion sensing, and biological applications

• Aisha Kanwal,
• Naheed Bibi,
• Sajjad Hyder,
• Arif Muhammad,
• Hao Ren,
• Jiangtao Liu and
• Zhongli Lei

Beilstein J. Nanotechnol. 2022, 13, 1068–1107, doi:10.3762/bjnano.13.93

• ]. Godavarthi et al. used seaweed (Sargassum fluitans) to synthesize N-CDs. 1H NMR and 13C NMR were used to analyze Sargassum fluitans and showed that amino acids acted as a nitrogen source, for the preparation of N-CDs. The reported N-CDs were used as a fluorescence probe to detect DNA, and gel electrophoresis

Impact of device design on the electronic and optoelectronic properties of integrated Ru-terpyridine complexes

• Max Mennicken,
• Sophia Katharina Peter,
• Corinna Kaulen,
• Ulrich Simon and
• Silvia Karthäuser

Beilstein J. Nanotechnol. 2022, 13, 219–229, doi:10.3762/bjnano.13.16

• precursor [Ru(acetone)6](PF6)3 (Ru-PF6) were prepared according to procedures previously described [15][19][25][26][27]. The analysis of the prepared substances, including 1H NMR, UV–vis spectroscopy and mass spectrosmetry, display a high purity [15]. The molecular formulas of the chemical compounds are

Fate and transformation of silver nanoparticles in different biological conditions

• Barbara Pem,
• Marija Ćurlin,
• Darija Domazet Jurašin,
• Valerije Vrček,
• Rinea Barbir,
• Vedran Micek,
• Raluca M. Fratila,
• Jesus M. de la Fuente and
• Ivana Vinković Vrček

Beilstein J. Nanotechnol. 2021, 12, 665–679, doi:10.3762/bjnano.12.53

• , while the Ag signal evidenced that the captured particles were generated from AgNPs by the reductive power of CYS (Figure 7a) or GSH (Figure 7b). Finally, the fate of GSH during the formation of AgNPs was monitored by 1H NMR spectroscopy (Figure 8). The reaction was conducted in 25 mM of PB to maintain

• the pH close to neutral, since the synthesis does not progress in water due to the acidic nature of GSH. The 1H NMR spectrum of 10 mM GSH in PB was recorded (Figure 8b). It showed four distinct peaks corresponding to protons bound to carbon at positions nine (overlapped with two), seven, four, and

• free GSH (5 mM) and a mixture containing 5 mM of GSH and 10 mM of AgNO3 in PB after 2 h of incubation at 25 °C were obtained. The samples were prepared with the addition of D2O to a final concentration of 10% (v/v). The 1H NMR spectra were recorded on a Varian INOVA 400 spectrophotometer (Varian

Gold(I) N-heterocyclic carbene precursors for focused electron beam-induced deposition

• Cristiano Glessi,
• Aya Mahgoub,
• Cornelis W. Hagen and
• Mats Tilset

Beilstein J. Nanotechnol. 2021, 12, 257–269, doi:10.3762/bjnano.12.21

• purified through column chromatography (DCM, silica). The product was obtained as an off-white powder (100.3 mg, 89%). 1H NMR (400 MHz, CD2Cl2) δ 4.29 (q, J = 7.3 Hz, 4H, -CH2-), 1.44 (t, J = 7.3 Hz, 6H, -CH3); 13C NMR (101 MHz, CD2Cl2) δ 174.1 (NHC-C), 116.9 (=C-Cl), 46.3 (-CH2-), 16.0 (-CH3); MS (ESI

• evapouration and the resulting white solid was partially dissolved in dichloromethane (DCM), filtered, and purified through column chromatography (DCM, silica). The obtained orange powder was precipitated from layering of DCM and pentane. The product was obtained as a white powder (89.2 mg, 72%). 1H NMR (600

• crystals were obtained (565 mg, 84%). 1H NMR (400 MHz, CD2Cl2) δ 8.05 (s, 1H, =CH-), 4.41 (q, J = 7.3 Hz, 2H, -CH2-, N side), 4.24 (q, J = 7.4 Hz, 2H, -CH2-, CH side), 1.53 (t, J = 7.4 Hz, 3H, -CH3, CH side), 1.51 (t, J = 7.3 Hz, 3H, -CH3, N side); 13C NMR (101 MHz, CD2Cl2) δ 173.2 (NHC-C), 142.2 (=CH

Cu₂O nanoparticles for the degradation of methyl parathion

• Juan Rizo,
• David Díaz,
• Benito Reyes-Trejo and
• M. Josefina Arellano-Jiménez

Beilstein J. Nanotechnol. 2020, 11, 1546–1555, doi:10.3762/bjnano.11.137

• operating at 200 kV. The 31P and 1H NMR spectra were recorded on an Agilent 400 MR DD2 spectrometer (Santa Clara, CA, USA) operating at 161 MHz for 31P and 400 MHz for 1H. The 31P and 1H chemical shifts were measured in deuterated chloroform (CDCl3) or water (D2O) relative to tetramethylsilane (TMS) for 1H

• and consequently methyl parathion is also removed and therefore absent in the NMR spectra. Figure 6 is the 1H NMR spectrum of the degradation products obtained with Cu2O NPs of 29 nm using D2O as solvent. The chemical shifts at 6.8 and 8.1 ppm belong to the coupled protons (d, J = 9 Hz) of 4

• -nitrophenol. The peaks at 3.45 and 3.48 ppm are the methyl groups of phosphate, which show coupling to phosphorous, and the peak at 4.65 ppm is due to the HDO produced by the deuterium interchange with the hydroxyl group of 4-nitrophenol. D2O was used as solvent for 1H NMR instead, of CDCl3 like in 31P NMR

Role of redox-active axial ligands of metal porphyrins adsorbed at solid–liquid interfaces in a liquid-STM setup

• Thomas Habets,
• Sylvia Speller and
• Johannes A. A. W. Elemans

Beilstein J. Nanotechnol. 2020, 11, 1264–1271, doi:10.3762/bjnano.11.110

• obtained chemicals were used without further purification unless stated otherwise. The purity of 1-phenyloctane, the solvent in which the additional currents were observed, was confirmed by 1H NMR spectroscopy; moreover, the currents were observed in multiple batches of this solvent, of two different

Straightforward synthesis of gold nanoparticles by adding water to an engineered small dendrimer

• Sébastien Gottis,
• Régis Laurent,
• Vincent Collière and
• Anne-Marie Caminade

Beilstein J. Nanotechnol. 2020, 11, 1110–1118, doi:10.3762/bjnano.11.95

• DMSO was the solvent used, several sets of doublets were observed within the same region (Supporting Information File 1, Figure S6) presumably due to the presence of both the Z and E-isomers of the hydrazones [51]. These isomers were also detected in the 1H NMR spectra as two signals corresponding to

• . The hydrazone/hydrazine equilibrium was also seen when compound 3 was placed into DMSO-containing water, leading to the reappearance of a small signal corresponding to the aldehydes in the 1H NMR spectrum (Figure S9, Supporting Information File 1). The released Girard's T reagent should act as a

• solution was stirred for 1 h and evaporated until dry. Then the product was rinsed with CH2Cl2/pentane (1:5) and filtered. Next, the crude product was evaporated until dryness in order to obtain 152.5 mg (quantitative yield) of the complex 2 as a white foam. 31P {1H} NMR (101 MHz, CDCl3) 23.2 (d, 2JPP = 27

A 3D-polyphenylalanine network inside porous alumina: Synthesis and characterization of an inorganic–organic composite membrane

• Jonathan Stott and
• Jörg J. Schneider

Beilstein J. Nanotechnol. 2020, 11, 938–951, doi:10.3762/bjnano.11.78

• and n-pentane. The colorless needles were filtered, washed with anhydrous n-pentane, dried under vacuum and stored under inert gas atmosphere at −28 °C until early use. Phenylalanine-NCA: 1H NMR (500 MHz, THF-d8), δ: 2.86 (dd, 1H), 3.06 (dd, 1H), 4.48 (m, 1H), 7.17 (m, 5H), 7.80 (s, 1H) ppm. 13C NMR

Interfacial charge transfer processes in 2D and 3D semiconducting hybrid perovskites: azobenzene as photoswitchable ligand

• Nicole Fillafer,
• Tobias Seewald,
• Lukas Schmidt-Mende and
• Sebastian Polarz

Beilstein J. Nanotechnol. 2020, 11, 466–479, doi:10.3762/bjnano.11.38

• maximum at 325 nm is assigned to the S0→S2 transition and loses intensity over the time of irradiation (Figure 1C). The signal of the S0→S1 transition at 425 nm shows much weaker absorption in the beginning, which increases over the time of irradiation. Using 1H NMR (Figure 1E) the degree of isomerisation

• azobenzene molecules in our materials were determined using a combination of methods. A quantitative assertion can be made using 1H NMR spectroscopy of the dissolved particles, which gives a DOI. The conformational change is accompanied by a reduction of the molecule length, which is why a change in layer

• thickness should be observable in PXRD measurements. After irradiation of a dispersion of 2D-AzoC2, 2D-AzoOC4 and 2D-AzoOC12 at λ = 313 nm for 600 s, the materials were dissolved in MeOD and 1H NMR was measured (Figure 2E). According to UV–vis kinetic measurements of the dispersed materials a time period of

Nanoparticles based on the zwitterionic pillar[5]arene and Ag⁺: synthesis, self-assembly and cytotoxicity in the human lung cancer cell line A549

• Dmitriy N. Shurpik,
• Denis A. Sevastyanov,
• Pavel V. Zelenikhin,
• Pavel L. Padnya,
• Vladimir G. Evtugyn,
• Yuriy N. Osin and
• Ivan I. Stoikov

Beilstein J. Nanotechnol. 2020, 11, 421–431, doi:10.3762/bjnano.11.33

• obtained by 1Н NMR spectroscopy unfortunately did not allow us to determine the nature of the interaction by changing the position of the host and guest chemical shifts. The changes that were recorded in the 1H NMR spectrum of the 3/Ag+ system (1:1, 10−3 M) were related to the broadening of the macrocycle

• concentration of silver ions of 30 μM and 55% for a concentration of silver ions of 40 μM. The results can be used to create new antibacterial materials and 2D biomedical coatings. Experimental 1H NMR, 13C and 2D NOESY NMR spectra were obtained on a Bruker Avance-400 spectrometer (13С{1H} – 100 MHz and 1H and

• with distilled water. The organic layer was separated and dried (molecular sieves, 3 Å), and the solvent was removed under reduced pressure. The residue was dried under reduced pressure for 30 min and a light-yellow viscous oil was obtained. Yield 0.34 g (89%). 1H NMR (400 MHz, DMSO-d6, 298 K) δ (ppm

Rational design of block copolymer self-assemblies in photodynamic therapy

• Maxime Demazeau,
• Laure Gibot,
• Anne-Françoise Mingotaud,
• Patricia Vicendo,
• Clément Roux and
• Barbara Lonetti

Beilstein J. Nanotechnol. 2020, 11, 180–212, doi:10.3762/bjnano.11.15

The different ways to chitosan/hyaluronic acid nanoparticles: templated vs direct complexation. Influence of particle preparation on morphology, cell uptake and silencing efficiency

• Arianna Gennari,
• Julio M. Rios de la Rosa,
• Erwin Hohn,
• Maria Pelliccia,
• Enrique Lallana,
• Roberto Donno,
• Annalisa Tirella and
• Nicola Tirelli

Beilstein J. Nanotechnol. 2019, 10, 2594–2608, doi:10.3762/bjnano.10.250

• ]. Experimental Materials and methods The list of chemicals used is provided in Supporting Information File 1, Section SI1.1. Chitosan of viscosity average molecular weight 656 kDa and a degree of deacetylation (DD) of 85% (from 1H NMR; hereafter referred to as Chit650 or high-MW chitosan) was purchased from

Mobility of charge carriers in self-assembled monolayers

• Zhihua Fu,
• Tatjana Ladnorg,
• Hartmut Gliemann,
• Alexander Welle,
• Asif Bashir,
• Michael Rohwerder,
• Qiang Zhang,
• Björn Schüpbach,
• Andreas Terfort and
• Christof Wöll

Beilstein J. Nanotechnol. 2019, 10, 2449–2458, doi:10.3762/bjnano.10.235

• aqueous NH4Cl solution was added and the product extracted with dichloromethane. The extract was filtered through a pad of silica, evaporated to dryness and recrystallized from methylcyclohexane, yielding 9.1 g (85%) of a yellow solid. 1H NMR (CDCl3, 400 MHz) δ 8.22 (s, 1H, H-10), 8.20 (s, 1H, H-9), 8.02

• solution (1.0 mol/L in THF, 12 mmol) were added dropwise. Stirring at room temperature was continued for 1 h and then 50 mL of H2O were added. The product was extracted with dichloromethane and filtered through a plug of silica. Evaporation of the volatiles resulted in 2 g of a brownish solid (90%). 1H NMR

• dichloromethane followed by warm ethyl acetate. The polar eluates were combined and the volatiles removed in vacuo. The remaining material was recrystallized from chloroform to yield 1 g of a brown solid (44%). 1H NMR (DMSO-d6, 250 MHz) δ 8.63 (s, 2H, H-10, H-9), 8.37 (s, 1H, H-1), 8.17–8.08 (m, 3H, H-5, H-8, H-4

Air oxidation of sulfur mustard gas simulants using a pyrene-based metal–organic framework photocatalyst

• Ghada Ayoub,
• Mihails Arhangelskis,
• Xuan Zhang,
• Florencia Son,
• Timur Islamoglu,
• Tomislav Friščić and
• Omar K. Farha

Beilstein J. Nanotechnol. 2019, 10, 2422–2427, doi:10.3762/bjnano.10.232

• overoxidation of CEES to 2-chloroethyl ethyl sulfone (CEESO2) was observed, as demonstrated by 1H NMR spectroscopy (Figure S6, Supporting Information File 1). Conclusion In summary, we demonstrated NU-400, a microporous MOF based on a pyrene-2,7-dicarboxylate linker as a highly effective platform for singlet

Mannosylated brush copolymers based on poly(ethylene glycol) and poly(ε-caprolactone) as multivalent lectin-binding nanomaterials

• Stefania Ordanini,
• Wanda Celentano,
• Anna Bernardi and
• Francesco Cellesi

Beilstein J. Nanotechnol. 2019, 10, 2192–2206, doi:10.3762/bjnano.10.212

• ), targeting a degree of polymerization (DP) equal to 5. Reaction conversions were monitored by means of 1H NMR analysis; almost full monomer conversion (99%) was obtained after 6 h. The dispersity of the purified polymer was 1.19. Subsequent methacrylation of the terminal hydroxy group was accomplished in

• number of pendant mannose, as well as the self-assembly behavior in water. Remarkably, when the ratios PEG/PCL were 9:1 or 8:2, the polymerizations achieved high conversions (≥87% after 6 h), as calculated from 1H NMR spectroscopy results (see Figure S2, Supporting Information File 1). The

• molecular weight calculated by 1H NMR from the value obtained by GPC (which was substantial for the four-arm polymers) was likely to be caused by the polystyrene calibration and by the intrinsic limitation of the GPC to determine the exact molecular weight of comb-like and hyperbranched polymers, as

Nitrogen-vacancy centers in diamond for nanoscale magnetic resonance imaging applications

• Alberto Boretti,
• Lorenzo Rosa,
• Jonathan Blackledge and
• Stefania Castelletto

Beilstein J. Nanotechnol. 2019, 10, 2128–2151, doi:10.3762/bjnano.10.207

Microbubbles decorated with dendronized magnetic nanoparticles for biomedical imaging: effective stabilization via fluorous interactions

• Da Shi,
• Justine Wallyn,
• Dinh-Vu Nguyen,
• Francis Perton,
• Delphine Felder-Flesch,
• Sylvie Bégin-Colin,
• Mounir Maaloum and
• Marie Pierre Krafft

Beilstein J. Nanotechnol. 2019, 10, 2103–2115, doi:10.3762/bjnano.10.205

• /DIPEA. Next, the removal of the carboxybenzyl group by hydrogenolysis allows for the introduction of the perfluoroalkyl chain via N-alkylation. Finally, treatment with trimethylsilyl bromide produced the desired fluorinated bisphosphonate dendron. Characterization of C2F5OEG8Den: 1H NMR (500 MHz, CD3OD

• . Characterization of C4F9OEG8Den: 1H NMR (500 MHz, CD3OD) δ 7.25 (s, 2H), 6.83 (s, 1H), 6.78 (s, 2H), 4.22 (t, J = 4.5 Hz, 6H), 4.14 (t, J = 5.6 Hz, 2H), 3.87 (t, J = 4.7 Hz, 4H), 3.80 (t, J = 4.6 Hz, 2H), 3.76–3.50 (m, 74H), 3.33 (s, 6H), 3.10–3.06 (m, 2H), 3.02 (d, 2JP-H = 21.0 Hz, 4H), 2.64–2.59 (m, 2H), 2.32

Synthesis of highly active ETS-10-based titanosilicate for heterogeneously catalyzed transesterification of triglycerides

• Muhammad A. Zaheer,
• David Poppitz,
• Khavar Feyzullayeva,
• Marianne Wenzel,
• Jörg Matysik,
• Radomir Ljupkovic,
• Aleksandra Zarubica,
• Alexander A. Karavaev,
• Andreas Pöppl,
• Roger Gläser and
• Muslim Dvoyashkin

Beilstein J. Nanotechnol. 2019, 10, 2039–2061, doi:10.3762/bjnano.10.200

Synthesis and potent cytotoxic activity of a novel diosgenin derivative and its phytosomes against lung cancer cells

• Liang Xu,
• Dekang Xu,
• Ziying Li,
• Yu Gao and
• Haijun Chen

Beilstein J. Nanotechnol. 2019, 10, 1933–1942, doi:10.3762/bjnano.10.189

• calculated. The novel Di derivative FZU-0021-194-P2 (P2) showed the most efficient suppression of cell growth (Figure 1). P2 was characterized by 1H NMR (Supporting Information File 1, Figure S1), 13C NMR (Supporting Information File 1, Figure S2) and HRMS. The structure of P2 was further established by X

• mL) and extracted with H2O (20 mL). The combined organic layers were washed with saturated brine, dried over anhydrous Na2SO4, filtered, which was purified by silica gel chromatography (PE/EtOAc 4:1) to give the desired product (348 mg, 38%) as a white solid. TLC: Rf = 0.54 (PE/EtOAc 2:1). 1H NMR

Toxicity and safety study of silver and gold nanoparticles functionalized with cysteine and glutathione

• Barbara Pem,
• Igor M. Pongrac,
• Lea Ulm,
• Ivan Pavičić,
• Valerije Vrček,
• Darija Domazet Jurašin,
• Marija Ljubojević,
• Adela Krivohlavek and
• Ivana Vinković Vrček

Beilstein J. Nanotechnol. 2019, 10, 1802–1817, doi:10.3762/bjnano.10.175

• , the mixture of a metallic salt (HAuCl4 or AgNO3), NaBH4, and CYS (as described above) was stirred under argon in ultrapure water at room temperature for 90 minutes. The progress of the reaction was monitored by 1H NMR spectroscopy. Aliquots were taken from the reaction mixture at selected time points

• and D2O was added (or a D2O-filled capillary was used for a lock signal). Along with the disappearance of the 1H NMR signals of the reactant (CYS), a new set of proton signals of the product emerged (Figure 1). All new signals were shifted downfield by approximately 0.2 ppm. According to detailed 1H

• and 13C NMR analysis (see Figures S2–S4 in Supporting Information File 1), we conclude that cystine was formed. After completion (no CYS signals in 1H NMR spectrum) the remaining signals were broadened in time, which indicates the binding of cystine to the NP surface. It is well known that 1H NMR

Biocatalytic oligomerization-induced self-assembly of crystalline cellulose oligomers into nanoribbon networks assisted by organic solvents

• Yuuki Hata,
• Yuka Fukaya,
• Toshiki Sawada,
• Masahito Nishiura and
• Takeshi Serizawa

Beilstein J. Nanotechnol. 2019, 10, 1778–1788, doi:10.3762/bjnano.10.173

• structure of the products was analyzed by 1H NMR spectroscopy and MALDI–TOF mass spectrometry. The NMR spectra of the representative products showed proton signals for cellulose oligomers (Figure 5). In addition, the mass spectra further revealed the successful synthesis of cellulose oligomers (Figure 6

• dispersions was dried at 105 °C for 24 h, followed by weighing. For 1H NMR spectroscopy, ATR-FTIR absorption spectroscopy, and XRD measurements, as much as possible of the supernatant after the final centrifugation was removed by pipette, followed by adding water to the products. The resultant product aqueous

• dispersions with residual organic solvents were lyophilized and then stored at 4 °C until use. Characterization of the products For NMR spectroscopy, the lyophilized products were dissolved in 4% NaOD/D2O to obtain product solutions (≥2% (w/v)). 1H NMR spectra were recorded on an AVANCE III HD500 spectrometer