Addition Reactions Research Articles

Efficient and facile dual post-polymerization modification using acetoacetate-acrylate Michael addition

Post-polymerization modification (PPM) is a valuable strategy for achieving diversified functional polymers; nonetheless, the pursuit of achieving mild and efficient dual modification along the polymeric backbone remains as a challenge. In this work, the Michael addition reaction of acetoacetates and acrylates have been demonstrated as a robust PPM technique. The reversible addition-fragmentation chain transfer polymerization of commercially available 2-(acetoacetoxy)ethyl methacrylate provides a polymer scaffold with controlled molecular weight and acetoacetate groups. These pendant groups are capable of undergoing efficient double addition reactions with acrylates, leading to an increased density of functional moieties within the polymeric backbone. This PPM reaction exhibits unique advantages such as mild reaction conditions (at 40 °C), rapid kinetics (completion within 1 h), and high atom economy. Consequently, a series of polymers with tunable thermal stability, glass transition temperature, and hydrophilicity have been successfully synthesized. Applications have been demonstrated for both the synthesis of polymers exhibiting aggregation-induced luminescence and the preparation of luminescent materials with adjustable mechanical properties. This pioneering work unveils a robust post-polymerization modification technique, significantly advancing the synthesis of innovative functional polymers.

Sustainable rewritable paper based on photoresponsive tungsten oxide quantum dots for anti-counterfeiting and waterproofing

Ink-free printing using photochromic paper has emerged as a promising technology for information recording, transmission, and secure interaction applications. Tungsten oxide quantum dots (WO3 QDs), with their rapid UV response, excellent photochemical stability, and outstanding fatigue resistance, exhibit significant potential as an ink-free medium in the construction of sustainable rewritable paper. However, challenges such as low binding force, poor stability, and weak scalability limit the development of reversible photochromic paper based on WO3. In this study, a novel sustainable rewritable paper based on a scalable strategy of covalent modification and hydrophobic layer protection has been reported. Specifically, cellulose papers modified with silane coupling agent were directly grafted with amino-modified WO3 QDs by covalent bonding through the addition reaction between epoxy and amine groups. Subsequently, the sustainable rewritable paper was obtained by the deposition of hydrophobic layer of polydimethylsiloxane (PDMS) via a dip-coating method. The rewritable paper exhibits exceptional properties, including high color contrast, extended color-retention (over 21 days), good rewritability (20 cycles) and excellent resistance to water or stains. Based on ink-free writing technology, the photo-responsive rewritable papers were utilized for anti-counterfeiting and encryption or decryption, demonstrating their great potential for information recording, storage, and security protection.

Recent Routes in Synthesis and Biological Activity of Pyrimido[4,5-b] Quinoline Derivatives: A Review (Part II)

The synthesis of organic molecules has been a tremendous and rapid advance in the recent decade to obtain high biological and pharmacological activities. In this review, the organic synthesis of pyrimido[4,5-b]quinoline derivatives is considered an alternative method to traditional procedures for treating many diseases that affect humans. Also, by transferring electrons, stereoselective syntheses occur via organic reactions in various unnatural and natural conditions at room temperature and normal pressure. We found that the structure of pyrimido[4,5-b]quinoline derivatives was formed by substrates, bases, electrophiles, and low-level and highly stable reagents that can be broadly applied to synthesize more heterocycles. These reagents include: 2- nitrobenzaldehyde; 3-(benzyloxy)-4-methoxy-2-nitrobenzaldehyde; 4,5-dimethoxy-2- nitrobenzaldehyde; 2-aminobenzaldehyde; 2-aminoquinoline-3-carboxamide; 2-chloroquinoline3-carbaldehyde; 2-bromobenzaldehyde; 2-chloroquinoline-3-carbonitrile; 2-chloroquinoline-3- carboxylic acid; aniline; phenyl-methanamine; amino-quinoline-3-carboxylic acid /aminoquinoline-carbonitrile; amino-6,7-dimethoxy-quinoline-3-carbonitrile; amino-oxolo [4,5- g]quinolin-carboxamide; 3-(aminomethyl) quinolin-2-amine; 4-aminobenzo[d][1,3] dioxole-5- carbaldehyde; thiourea; ethyl 3-oxo-butanoate; 2-cyano-acetamide; 2-(bis (methylthio) methylene) malononitrile; ethyl 3,3-diamino-2-cyanoacrylate; naphthalene-1,4-dione; and N-carbamoyl-2- cyanoacetamide derivatives. The prepared pyrimido[4,5-b]quinoline derivatives were described through means of the following chemical reactivity: alkylation, bromination, chlorination, cyclocondensation, cyclization, acylation, oxidation-reduction, dehydration, addition reaction and Vilsmeier-Haack reaction (Vilsmeier reagent).

Carbodiphosphorane-Activated Distibene and Dibismuthene Dications.

Low-valent antimony and bismuth have emerged as novel platforms for achieving reversible small-molecule activation at main-group metals. Although various examples of oxidative addition reactions at monomeric Sb(I) and Bi(I) have been reported, the chemistry of the heavy group 15 Sb(I)═Sb(I)/Bi(I)═Bi(I) double bonds toward small molecules remains largely unexplored. In this study, we present a straightforward synthesis of distibene and dibismuthene dications coordinated with a neutral carbodiphosphorane (CDP) ligand. The nonbonding interactions between the occupied p-orbital at the CDP ligand and the π-bonding orbital of the Sb═Sb/Bi═Bi bonds yield compounds with exceptionally small HOMO-LUMO gaps. In addition, the reduction of steric hindrance compared to known neutral derivatives stabilized with bulky aryl groups allows for better accessibility of the double bonds. This high reactivity is demonstrated in the oxidative addition of distibene to diphenyldisulfide as well as in [2+2] cycloadditions to alkynes. Additionally, the Sb═Sb bond reversibly adds to 2,3-dimethylbutadiene in a [4+2] cycloaddition reaction.

Ultrasound assisted enzymatic synthesis of OPO structured lipids by covalent organic framework immobilized lipase

In this study, the covalent organic framework immobilized Rhizomucor miehie lipase COF@RML as a novel biocatalyst was applied in the enzymatic synthesis of OPO structured lipids (1, 3-dioleoyl-2-palmitoylglycerol). The impact of reaction medium, substrate molar ratio, enzyme addition amount, reaction time and temperature on the enzymatic synthesis of OPO structured lipids were studied. Furthermore, the effects of ultrasonic power and ultrasonic time on the synthesis of OPO structural lipids were studied. The results showed that ultrasonication could increase the yeild of OPO structured lipids by improving substrate mass transfer and enzyme particle dispersion. The optimal process for the synthesis of OPO structured lipids was obtained. When the ultrasonic power was set at 90 W, ultrasonic time at 12 minutes, enzyme addition amount at 10 wt%, substrate molar ratio at 1:8, reaction temperature at 45 °C, and reaction time at 6 hours, the yield of OPO structured lipids reached a remarkable 51.27 %. Finally, the commercial lipase Lipozyme RM IM was compared with the COF@RML. The findings indicated that COF@RML immobilized enzyme had better application value in the synthesis of OPO structured lipids.

Chiral Bis(binaphthyl) Cyclopentadienyl Ligands for Rhodium-Catalyzed Desymmetrization of Diarylmethanes via Selective Arene Coordination.

Owing to substantial advances in the past several decades, transition-metal-catalyzed asymmetric reactions have garnered considerable attention as pivotal methods for constructing chiral molecules from abundant, readily available achiral counterparts. These advances are largely attributed to the development of chiral ligands that control stereochemistry through steric repulsion and other noncovalent interactions between the ligands and functional groups or prochiral centers on the substrates. However, stereocontrol weakens dramatically with increasing distance between the reaction site and the functional group or prochiral center. Herein, we report a symphonic strategy for remote stereocontrol of Rh(III)-catalyzed asymmetric benzylic C-H bond addition reactions of diarylmethanes in which the two aryl motifs differ at the meta and/or para position. Specifically, catalysts bearing a new type of chiral cyclopentadienyl (Cp) ligand differentiate between the two aromatic rings of the diarylmethane by arene-selective η6 coordination, setting up an opportunity for ligand-controlled stereoselective benzylic deprotonation and subsequent stereoselective addition to the 1,1-bis(arylsulfonyl)ethylene.

Sequential-Flow Synthesis of Donepezil: A Green and Sustainable Strategy Featuring Heterogeneous Catalysis and Hydrogenation.

An atom-economical sequential-flow synthesis of donepezil, a widely prescribed drug for Alzheimer's disease, was accomplished using inexpensive, commercially available precursors. This achievement was made possible by reconfiguring the synthetic route to include only heterogeneous catalytic addition and condensation reactions, with a particular emphasis on skeletal transformation and bond formation through hydrogenation processes. Notably, water was the sole byproduct in this synthesis. A crucial aspect of this work was the development of appropriate continuous-flow processes to achieve a one-flow synthesis. This was accomplished by implementing in-line treatments of the main reaction stream to eliminate inhibitory factors that could affect catalyst performance in the hydrogenation steps.

A solventless carbonyl addition reaction as a guided inquiry laboratory activity for second-year undergraduate organic students

ABSTRACT A less hazardous, environmentally friendly, and energy-efficient Knoevenagel reaction performed using proline as a catalyst has been designed and implemented within a sophomore-level organic chemistry laboratory as a guided inquiry activity. The main learning objective is to enable students to identify and understand various green chemistry principles such as atom economy, use of safer chemicals, design for energy efficiency, and inherently safer chemistry for accident prevention. Students were successful in synthesizing α,β-unsaturated diesters using unknown substituted benzaldehydes (later identified by the students spectroscopically) and Meldrum’s acid at room temperature in the presence of proline as a catalyst without the need for an additional base. By analyzing 1H NMR spectroscopic data, infrared spectroscopy, and mass spectrometry to identify the synthesized product, the unknown benzaldehyde starting material, and the major reaction pathway, students have enhanced their spectroscopy skills and developed a deeper understanding of the mechanism of the reaction that may not be covered in the lecture course.

Design and Evaluation of a Reprocessable Bismaleimide Thermoset: Enhancing Functionality and Sustainability Compatibility.

Bismaleimide (BMI) resins are high-performance thermosets that are primarily used in aerospace because of their exceptional heat resistance and physical properties. However, their growing demand has led to significant environmentally unfriendly waste. To address this, our research proposes a reprocessable BMI system using a newly synthesized BMI vitrimer (BMIV) with functional groups that form covalent adaptable networks (CANs). To enhance the properties, a symmetrical BMI with two ester groups introduced into the rigid rod molecule was designed as a CAN component. After confirming the structure using various spectroscopic techniques, BMIV was coupled with aromatic diamines via an additional aza-Michael reaction to obtain the cured resins. Subsequently, the mechanical properties and reprocessing behavior of the thermally stable and optimized thermosetting material with the best performance were evaluated, and the evidence, mechanism, and activation energy of the topology rearrangement are reported in detail.

Preparation of a bifunctional precursor with antibacterial and flame retardant properties and its application to cotton fabrics

Cotton fabric is a cellulose-based material with complex capillary spaces, which enhance breathability and softness. However, these capillary spaces can promote bacterial growth with moisture during storage and daily use. Additionally, cotton fibers are highly flammable, posing a fire hazard to wearer. The lack of inherent antibacterial and flame retardant properties in cotton fabric limits its applications. In this paper, the triazole compound containing Schiff base (NABTA) was synthesized from 3-bromopropene, p-hydroxybenzaldehyde and 3-amino-1,2,4-triazole, followed by an addition reaction between Schiff base activity and 9,10-dihydro-9-oxa-10-phospha-phenanthrene-10-oxide (DOPO) to synthesize an antibacterial and flame retardant precursor (NABTA-DOPO). The structure of NABTA and NABTA-DOPO was characterized by FTIR and NMR. NABTA and NABTA-DOPO were applied to cotton fabrics to investigate and compare their antibacterial properties and thermal stability. The results showed that all the cotton fabrics treated with NABTA and NABTA-DOPO had favorable antibacterial effects. The introduction of DOPO had no significant effect on the antibacterial effect and mechanism of the fabrics. However, it otherwise improved the burning stability of treated cotton fabrics. The antibacterial activity of 10 g/L NABTA-DOPO treated cotton fabrics after chlorination against E. coli and S. aureus was over 99.99 %. The vertical burning test results showed that cotton fabrics treated with a concentration of 50 g/L NABTA-DOPO had improved flame retardant properties with a damaged length of 5.9 cm. In addition, the storage, washability, UV stability and antibacterial reproducibility experiments demonstrated the excellent durability and reproducibility of the N-halamine structure of chlorinated cotton fabrics. This study enhances cotton fabric by synthesizing and applying NABTA and NABTA-DOPO, resulting in improved multifunctionalities, including antibacterial properties, flame retardancy, UV resistance, and wettability.

Photocatalytic Decarboxylative Alkylation of Cyclic Imine-BF3 Complexes: A Modular Route to Functionalized Azacycles.

Alkyl radicals generated via an acridine photocatalyzed decarboxylation reaction of feedstock carboxylic acids engage with a range of cyclic imine-BF3 complexes to provide α-functionalized azacycles in an operationally simple process. A three-component variant of this transformation incorporating [1.1.1]propellane as an additional reaction partner enables the synthesis of valuable bicyclopentane (BCP)-containing azacycles. Reactions exhibit good functional group compatibility, enabling late-stage modification of complex bioactive molecules.

Diverse Strategies to Develop Poly(ethylene glycol)-Polyester Thermogels for Modulating the Release of Antibodies.

In this work, we present basic research on developing thermogel carriers containing high amounts of model antibody immunoglobulin G (IgG) with potential use as injectable molecules. The quantities of IgG loaded into the gel were varied to evaluate the possibility of tuning the dose release. The gel materials were based on blends of thermoresponsive and degradable ABA-type block copolymers composed of poly(lactide-co-glycolide)-b-poly(ethylene glycol)-b-poly(lactide-co-glycolide) (PLGA-PEG-PLGA) or poly(lactide-co-caprolactone)-b-poly(ethylene glycol)-b-(lactide-co-caprolactone) (PLCL-PEG-PLCL). Primarily, the gels with various amounts of IgG were obtained via thermogelation, where the only factor inducing gel formation was the change in temperature. Next, to control the gels' mechanical properties, degradation rate, and the extent of antibody release, we have tested two approaches. The first one involved the synergistic physical and chemical crosslinking of the copolymers. To achieve this, the hydroxyl groups located at the ends of the PLGA-PEG-PLGA chain were modified into acrylate groups. In this case, the thermogelation was accompanied by chemical crosslinking through the Michael addition reaction. Such an approach increased the dynamic mechanical properties of the gels and simultaneously prolonged their decomposition time. An alternative solution was to suspend crosslinked PEG-polyester nanoparticles loaded with IgG in a PLGA-PEG-PLGA gelling copolymer. We observed that loading IgG into thermogels lowered the gelation temperature (TGEL) value and increased the storage modulus of the gels, as compared with gels without IgG. The prepared gel materials were able to release the IgG from 8 up to 80 days, depending on the gel formulation and on the amount of loaded IgG. The results revealed that additional, chemical crosslinking of the thermogels and also suspension of particles in the polymer matrix substantially extended the duration of IgG release. With proper matching of the gel composition, environmental conditions, and the type and amount of active substances, antibody-containing thermogels can serve as effective IgG delivery materials.

Synthesis and mechanism of Bi/SnO2 for enhanced photocatalytic activity in the degradation of humic acid under visible light

Humic acid (HA) is a typical refractory organic matter, widely existing in natural water and many types of wastewaters. In this study, Bi/SnO2 composites were synthesized by a simple one-step hydrothermal method for photocatalytic degradation of HA. Due to the surface plasmon resonance (SPR) effect of Bi, the light absorption of Bi/SnO2 composites expands from UV to visible light compared to pure SnO2. Under visible light irradiation for 120 min, the UV254 removal reached 93.58 %, color number (CN) removal reached 94.41 %. The degradation rate constant of Bi/SnO2 (0.0178 min−1) is 14.83 times higher than that of SnO2 (0.0012 min−1), indicating the superior photocatalytic degradation efficiency of Bi/SnO2 composites. Fourier transform ion cyclotron resonance mass spectrometry (FT-ICR MS) was found that photocatalysis mainly degraded most CHO-containing organic matter and reduced the amount of organic matter (from 7240 to 3886). The molecular number of organic compounds with m/z of 400–500 and 500–600 exhibited a significant decrease, specifically by 1052 and 770, respectively. This observation suggests that the photocatalytic process effectively eliminates low and moderate molecular weight organics. The molecular number, aromaticity and molecular weight of dissolved organic matter (DOM) were reduced mainly by carboxylic acid reaction, dealkylation reaction and oxygen addition reaction.

Quantitative and mechanistic elucidation of the reactive oxygen species for effective sulfamethoxazole removal in heterogeneous peroxymonosulfate activated by MOFs-derived cladding structure CoZn/NC@UiO

In cobalt-based catalyst/peroxymonosulfate (PMS) systems, the key issues are the leaching of metals and the stability of catalysts. In this study, a NH2-UiO-66 cladded CoZn/NC catalyst was synthesized for efficient degradation of sulfamethoxazole (SMX) using activated PMS. The removal efficiency of SMX could achieve 100% within 30 min. The leaching of Co2+ was inhibited to 0.05 ppm and the anti-interference and cyclic stability of the catalyst were enhanced by the NH2-UiO-66 shell. In addition, the quenching experiment, electron paramagnetic resonance (EPR) technique and probe experiment were used to analyze the reactive oxygen species (ROSs) qualitatively and quantitatively. The findings demonstrated that singlet oxygen (1O2) had the highest steady-state and cumulative concentration. However, 1O2 could only participate in the degradation of SMX through single electron transfer or addition reaction, resulting in a lower second-order rate constant of the SMX reaction with 1O2. Sulfate radical (SO4·-) contributed the most to the degradation of SMX due to the high reactivity of the sulfonamide structure in SMX to SO4·-. Finally, possible pathways for SMX degradation were proposed. The two primary mechanisms of SMX degradation were S-N cleavage and amino hydroxylation/oxidation. The toxicity of most of the intermediates was less than that of SMX through ecological structure–activity relationship analysis. Overall, a novel approach to synthesize low leaching and efficient cobalt based catalyst was put forward, and the activation mechanism of PMS was also revealed.

Exploration of altered reaction pathways in aging pyrotechnic compositions under seasonal cycles

Since pyrotechnic delays are utilized to control the initiation timing of the metal-rich chemical reactions, precise control of these reactions is desired even when the combustion mixture is subjected to extended storage conditions. However, alterations in physicochemical and geometrical properties, accompanied by changes in thermal behavior, significantly influence the reaction pathways. This study explores the reactions of tungsten (W)-based pyrotechnic compositions subjected to aging. In particular, the work identifies the altered reaction pathways and fundamental causes leading to deterioration in both thermodynamic and physicochemical characteristics due to aging under seasonal cycles. Surface analyses revealed the major aging products as KClO3, WO3, BaO, and Cr2O3, along with three distinct effects of aging: pre-oxidation of metals, a priori decomposition of oxidizers, and surface cracking. Thermal analyses using peak deconvolution techniques described the sub-reactions of the major exothermic reaction, such as chemical reactions #1: (W and KClO4) and #2: (W, KClO4, and BaCrO4) and (WO3 and BaO). Notably, samples aged longer than 2 weeks underwent an additional side reaction, #3: (KClO3 decomposition). The multi-step reaction kinetics obtained from the Friedman method disclosed notably distinct trends in both pristine and aged samples. Among the aging products, KClO3 played a decisive role in altering the Eα-α relationship from a monotonic increase to a convex pattern. The measured decrease in Eα due to the involvement of KClO3 was approximately 30 % (from 464.7 kJ/mol to 272.4 kJ/mol). This demonstrates that KClO3 is critical to performance degradation, as it can release excess oxygen at initiation and decompose at a later stage. This results in incomplete combustion and a decline in thermodynamic performance due to the resulting ad-hoc O/F ratio. Thus, these findings may help in designing the time delay margins and estimating the shelf-life of these compositions.

Rare earth oxide promoted Ru/Al2O3 dual function materials for CO2 capture and methanation: An operando DRIFTS and TGA study

Dual-function materials (DFMs) combine sorbent and catalytic components to perform selective CO2 capture and subsequent hydrogenation. This study explores the performance of rare-earth oxides (REOs) as CO2 adsorption sites on Ru/Al2O3. REOs increase CO2 uptake by upwards of +60 % by enhancing the overall catalyst surface basicity and favoring metal–support interactions. Thermogravimetric analysis during CO2 adsorption-hydrogenation cycles exhibited significant catalytic activity and enhanced stability of Ru-REO/Al2O3 at temperatures as low as 200 °C. This leads to methane production of 50–85 µmol g−1, surpassing recently reported values obtained for alkali and alkali-earth promoted Ru-based materials operated at 250 °C. The highest performing studied DFM, RuNd2O3/Al2O3, achieved 85 % CO2 capture efficiency and steadily produced methane in cyclic operation (+120 % CO2 uptake relative to Ru/Al2O3). Operando DRIFTS revealed that the dominant mechanism for methane formation is the hydrogenation of ruthenium carbonyls, which are stabilized by REOs. Upon CO2 exposure, surface carbonates and bicarbonate species form more abundantly on DFMs than on Ru/Al2O3. This confirms that REOs enhance the adsorption and retention of carbonates, which generate additional promoter-related reaction pathways during low-temperature hydrogenation. These findings are crucial in the advancement of sustainable, wider operation range carbon capture and utilization technologies.

Bis(imidazolidine)-Derived NCN Nickel-Pincer-Catalyzed Asymmetric Reactions.

A bis(imidazolidine)-derived NCN nickel-pincer complex (tBu-PhBidine-Ni-OTf: NCN-Ni-OTf) was synthesized by the oxidative addition of imidazolidine-containing aryl triflate to Ni(cod)2 in MeCN. NCN-Ni-OTf exhibited asymmetric induction in three reactions. In the Friedel-Crafts reaction of indoles with N-Boc imines, 3-indolylmethanamine products were obtained in 79% yield with 99% ee. In a conjugate addition reaction of malononitrile to nitroalkenes, products were obtained in 95% yield with 75% ee. In iodolactonization, the pincer-Ni complex showed catalytic activity superior to that of tBu-PhBidine-Pd-OTf.

Protective Coatings Based on the Organosilicon Derivatives of Fatty Acids Obtained by the Thiol-Ene Click Reaction.

This article describes the synthesis of a hydrophobic protective coating for concrete based on a silane derivative of fatty acids. The coating was obtained through a thiol-ene click addition reaction using methyl oleate and 3-mercaptopropyltrimethoxysilane in the presence of the photoinitiator 2,2-dimethoxy-2-phenylacetophenone (DMPA). This reaction proved to be more efficient compared with other tested (photo)initiators, considering the double bond conversion of oleate. The coating was applied to concrete using two methods: immersion and brushing. Both methods exhibited similar consumption of methyl oleate-based silane (UVMeS) at approximately 20 g/m2. The hydrophobic properties of the coatings were evaluated based on the contact angle, which for the modified surfaces was above 93°, indicating their hydrophobic nature. The penetration depth of the silane solution into the concrete was also studied; it was 5-7 mm for the immersion method and 3-5 mm for the brushing method. The addition of tetraethoxysilane (TEOS) to the silane solution slightly improved the barrier properties of the coating.

Density functional theory studies on combustion oxidative decomposition mechanism of 3,3,3-trifluoropropene

The environmentally friendly refrigerant 3,3,3-trifluoropropene (HFO-1243zf) suitable for refrigeration and heat pump systems has flammability. Based on density functional theory, the oxidation decomposition mechanism of 3,3,3-trifluoropropene was studied, including the main initial oxidation decomposition and subsequent reactions. The results indicate that among the initial thermal decomposition reactions, the reaction with the lowest energy barrier is simultaneous elimination of HF, followed by CC bond breaking to form ∙CF3. In the H abstraction reaction, the reaction energy barrier of H atom capture by ∙F is the lowest. In F abstraction reaction, the ∙H is the most active. In the addition reaction, the reaction energy barrier of ∙F is the lowest. The energy barriers of reactions involving different free radicals, from high to low, are: thermal decomposition, F abstraction, H abstraction and addition reaction. The subsequent reactions mainly involve the generation pathways of ∙CF3 and the formation of stable products.

Catechol-modified stabilizer facilitates impulsive ligand functionalization of particulates and membrane modification of cells

Ligand-functionalized particulates have received considerable attention for targeted drug delivery. Previous studies have reported several methods for functionalizing various molecules on the surfaces of nano- and micro-particulates which involve multiple steps, reaction buffers and chemicals, and long reaction times. Here, we report a single-step method that uses catechol chemistry to rapidly functionalize ligands on the surfaces of polymeric nanoparticles (NPs). We synthesized dopamine-conjugated poly (ethylene-alt-maleic acid) (D-PEMA) by performing a nucleophilic addition reaction between dopamine and poly (ethylene-alt-maleic anhydride) (PEMAnh). We then used D-PEMA as a stabilizer while preparing NPs which led to the construction of NPs that were non-adhesive per se but provided active sites for conjugating multiple different ligands in an alkaline buffer via Michael's addition and Schiff's base substitution reactions. The ligand-functionalized NPs were nontoxic and effectively internalized by both primary and cancer cells. In addition, NPs prepared using the modified stabilizer conjugated rapidly on the surfaces of pancreatic islets in alkaline conditions. Our study provides evidence that the modified stabilizer is versatile and has the potential for drug delivery applications and cell surface modifications.