Hexyl Isocyanate Research Articles

Synthesis and characterization of statistical and block copolymers of n‐hexyl isocyanate and 2‐chloroethyl isocyanate via coordination polymerization

AbstractStatistical and block copolymers of n‐hexyl isocyanate (HIC) and 2‐chloroethyl isocyanate (ClEtIC) were synthesized via cοοrdination polymerization employing the half‐titanocene complex [(η5‐C5H5)((S)‐2‐Bu‐O)TiCl2] as initiator. The complex, bearing a chiral substituent, led to optically active products, as confirmed by circular dichroism measurements. The molecular characterization of all products was carried out by NMR and IR spectroscopy and size exclusion chromatography (SEC), while their thermal stability was investigated through differential scanning calorimetry (DSC), thermogravimetric analysis (TGA), and differential thermogravimetry (DTG). The reactivity ratios of the two monomers were determined using various graphical methods, as well as the COPOINT program, according to the terminal copolymerization model. Structural parameters, such as the dyad monomer sequences and the mean sequence lengths were calculated as well. In addition, the kinetics of the thermal degradation of the statistical copolymers was studied, and the activation energies of the thermal degradation were calculated employing the Kissinger, Ozawa–Flynn–Wall (OFW), and Kissinger–Akahira–Sunose (KAS) methods. The block copolymers were synthesized by sequential addition of monomers starting from the polymerization of HIC. Well‐defined products were obtained in a controlled way as revealed by SEC, IR, and NMR measurements.

Lyotropic Nematic Phases of Isotropic Nanoparticles via Semiflexible Polymer Ligands.

Lyotropic liquid crystalline(LC) nanomaterials are normally achieved through particle shape anisotropy. Herein, it is shown that lyotropic nematic rather than cubic phases are produced from sphericalnanoparticles (NPs) with semi-flexible polymer ligands. ZrO2 nanocrystals (4nm dia.) are coated with a dense shell of poly(hexyl isocyanate) (PHIC), a helical rod-like polymer that forms lyotropic LC phases in a range of organic solvents. Solvent casted NPs with PHIC ligands above the persistence length form linear assemblies, separated by a characteristic distance related to the chain length while NPs with shorter, rigid rod PHIC ligands pack hexagonally. Concentrated NP-PHIC dispersions present nematic textures similar to the free PHIC nematic solutions but at lower critical concentrations, widening the isotropic-nematic biphasic region. 2 H NMR spectra of the NPs dispersed in a deuterated solvent display quadrupolar splittings that increase with NP concentration, showing that the PHIC ligands are magnetically aligned. The high degree of orientation order is evidence that splaying of the ligand shell transforms the spherical NPs to rod-like shapes that assemble to produce nematic lyotropic LC phases and linear NP arrays. This approach to creating anisotropic assemblies can be extended to other types of spherical NPs and semiflexible polymers.

Facile synthesis of porphyrin-conjugates as amphiphilic modified photosensitizer structures of m-THPP bearing carbamate, carboxylate and sulfonate linkers

5,10,15,20-Tetrakis(3-hydroxyphenyl)porphyrin (m-THPP) bearing various nitrogen and sulfur containing heterocycles, aromatic, aliphatic and alicyclic residues covalently linked to the oxygen atom of the meta-hydroxy group of the porphyrin unit were synthesized in good yields as potential photosensitizers for photodynamic therapy (PDT). These new amphiphilic conjugates were designed to use three different polar linkers (carboxylate, sulfonate, and carbamate linker units)via the reaction of m-THPP with nicotinoyl chloride hydrochloride (carboxylate linker), 5-bromothiophene-2-sulfonyl chloride (sulfonate linker), phenyl isocyanate, 3,5-bis(trifluoromethyl)phenyl isocyanate, hexyl isocyanate and cyclohexyl isocyanate (carbamate linker). The heterocycles employed are 5- and 6-membered rings with different solubility characteristics.

High-performance family of polymeric particles prepared from poly(phenylene oxide)-poly(hexyl isocyanate) liquid crystal block copolymer: synthesis and properties study

The poly (phenylene oxide)-block-poly (hexyl isocyanate) copolymers (PPO-b-PHIC)s were synthesized in various ratios of blocks using the organotitanium coordination method at room temperature. The copolymer particles were prepared by precipitation of concentrated solution of the copolymers in non-solvent under stirring. The synthesized copolymers and their particles were characterized by 1H and 13C nuclear magnetic resonance (1H and 13C NMR), Fourier transform infrared (FTIR) spectra, differential scanning calorimetry (DSC), polarized optical microscope (POM), thermogravimetric analysis (TGA) and scanning electron microscope (SEM). The effect of block ratio on the anisotropic-isotropic transition and liquid crystal texture of copolymers as a function of temperature and concentration of the solution was investigated. The polymeric particles tend to be aligned along the fibrillar direction by increasing the block ratio of amide in the copolymer.

Metal-free anionic polymerization ofn-hexyl isocyanate catalyzed by phosphazene bases

Metal-free anionic polymerization ofn-hexyl isocyanate (HIC) catalyzed by phosphazene bases in THF at −98 °C under 10−6Torr was attempted to obtain poly(n-hexyl isocyanate) (PHIC) peptide mimics with a high purity.

Synthesis and characterization of brush diblock and triblock copolymers bearing polynorbornene backbone and poly(l‐lactide) and/or poly(hexyl isocyanate) side chains by a combination of coordination and ring opening metathesis polymerization

ABSTRACTWe report the synthesis of poly(l‐lactide) and poly(hexyl isocyanate) macromonomers using bischloro‐η5‐cyclopentadienyl(bicyclo[2.2.1]‐hept‐5‐en‐2‐oxy) Titanium (IV), [CpTiCl2(O‐NBE)]. These macromonomers bearing a norbornene end group were polymerized towards brush copolymers employing Grubbs' first generation catalyst. Brush copolymers consisting of blocks with different side chains were synthesized. The polymers were characterized by Size Exclusion Chromatography, Nuclear Magnetic Resonance, and their thermal properties were investigated by Thermogravimetric Analysis, and Differential Scanning Calorimetry analysis. © 2017 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2017, 55, 3455–3465

Synthesis and characterization of chiral poly(l‐lactide‐b‐hexyl isocyanate) macromonomers with norbornenyl end groups and their homopolymerization through ring opening metathesis polymerization to afford polymer brushes

ABSTRACTWe report the synthesis of the novel half‐titanocene alkoxide complex bischloro‐η5‐cyclopentadienyl(bicyclo[2.2.1]‐hept‐5‐en‐2‐oxy) titanium (IV), [CpTiCl2(O‐NBE)]. This complex was employed for the synthesis of chiral poly(l‐lactide‐b‐hexyl isocyanate) diblock copolymer bearing a norbornene end group with sequential addition of monomers. The poly(hexyl isocyanate) block is chiral due to the last l‐lactide unit of the poly(l‐lactide) block. This macromonomer was polymerized towards a chiral polymer brush structure with polynorbornene backbone and chiral poly(l‐lactide‐b‐hexyl isocyanate) side chains using Grubbs first‐generation catalyst. The polymers were characterized using size exclusion chromatography (SEC), nuclear magnetic resonance (NMR), and circular dichroism (CD) spectroscopy and their thermal properties were investigated by thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC) analysis. © 2017 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2017, 55, 1102–1112

A thermally and water activated shape memory gelatin physical hydrogel, with a gel point above the physiological temperature, for biomedical applications.

In this study, a science based approach is taken to monitor the variation of the properties, bioactivity and hydrogel formation behavior of gelatin upon functionalization with Ureido Pyrimidinone hexyl isocyanate (UPy synthon), which results in reversible physical network formation. UPy functionalization was carried out at 50 °C in DMSO. The reaction completion was confirmed using FTIR and 1H-NMR spectroscopy. The degree of gelatin functionalization was found to be about 22% of the active sites according to UV-visible measurements. Hydrophilicity and swelling of gelatin were affected consequently. DSC analysis showed a significant decrease in the glass transition temperature of gelatin following UPy functionalization. Based on AFM observations, a clear micro-phase separation was induced in gelatin upon treatment. WAXS investigation showed a significant decrease in gelatin triple and single helices upon functionalization. According to rheological measurements GelUPy forms a physical network of higher stability than gelatin and a remarkable increase in elastic to viscous transition temperature from 41 °C to 83 °C was observed. GelUPy showed a clear temperature/water triggered shape memory behavior while retaining the temporary shape in the absence of these stimuli. GelUPy possesses better mechanical properties than gelatin in a wet state. Biocompatibility evaluation revealed that the viability of L929 fibroblasts remained intact on GelUPy. GelUPy, a biodegradable shape memory hydrogel, was successfully used as a controlled drug delivery matrix. Our results propose that GelUPy is a promising material in biomedical applications as a drug carrier and tissue engineering scaffold, while crosslinking with suspected toxic reagents such as glutaraldehyde is avoided.

The involvement of TRP channels in sensory irritation: a mechanistic approach toward a better understanding of the biological effects of local irritants.

Peripheral nerves innervating the mucosae of the nose, mouth, and throat protect the organism against chemical hazards. Upon their stimulation, characteristic perceptions (e.g., stinging and burning) and various reflexes are triggered (e.g., sneezing and cough). The potency of a chemical to cause sensory irritation can be estimated by a mouse bioassay assessing the concentration-dependent decrease in the respiratory rate (50% decrease: RD50). The involvement of the N. trigeminus and its sensory neurons in the irritant-induced decrease in respiratory rates are not well understood to date. In calcium imaging experiments, we tested which of eight different irritants (RD50 5-730ppm) could induce responses in primary mouse trigeminal ganglion neurons. The tested irritants acetophenone, 2-ethylhexanol, hexyl isocyanate, isophorone, and trimethylcyclohexanol stimulated responses in trigeminal neurons. Most of these responses depended on functional TRPA1 or TRPV1 channels. For crotyl alcohol, 3-methyl-1-butanol, and sodium metabisulfite, no activation could be observed. 2-ethylhexanol can activate both TRPA1 and TRPV1, and at low contractions (100µM) G protein-coupled receptors (GPCRs) seem to be involved. GPCRs might also be involved in the mediation of the responses to trimethylcyclohexanol. By using neurobiological tools, we showed that sensory irritation in vivo could be based on the direct activation of TRP channels but also on yet unknown interactions with GPCRs present in trigeminal neurons. Our results showed that the potency suggested by the RD50 values was not reflected by direct nerve-compound interaction.

Synthesis and characterization of chiral poly(alkyl isocyanates) by coordination polymerization using a chiral half‐titanocene complex

ABSTRACTA new chiral half‐titanocene complex, [CpTiCl2(O‐(S)−2‐Bu)], is synthesized and characterized by 1H and 13C NMR spectroscopy. This complex is employed for the coordination polymerization of n‐butyl and n‐hexyl‐ isocyanate leading to chiral polymers, as revealed by their CD spectra. Only the left‐handed helix is produced, due to the chiral (S)−2‐butoxy group, which is bound to the polymer chain end. The polymerization of 3‐(triethoxysilyl)propyl isocyanate produces less soluble polymers. On the other hand, phenyl isocyanate reacts slowly with the complex leading quantitatively and selectively to triphenyl isocyanurate. 2‐Ethylhexyl isocyanate is slowly and selectively cyclotrimerized in the presence of the half‐titanocene complex. However, a statistical copolymer of 2‐ethylhexyl isocyanate and hexyl isocyanate is produced. The reaction of benzyl isocyanate with the complex leads to a mixture of low molecular weight polymer and cyclotrimer. The polymers are characterized using SEC, NMR, and CD spectroscopy and their thermal properties are investigated by TGA/DSC analysis. © 2015 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2015, 53, 2141–2151

Synthesis of Isocyanate-Based Brush Block Copolymers and Their Rapid Self-Assembly to Infrared-Reflecting Photonic Crystals

The synthesis of rigid-rod, helical isocyanate-based macromonomers was achieved through the polymerization of hexyl isocyanate and 4-phenylbutyl isocyanate, initiated by an exo-norbornene functionalized half-titanocene complex. Sequential ruthenium-mediated ring-opening metathesis polymerization of these macromonomers readily afforded well-defined brush block copolymers, with precisely tunable molecular weights ranging from high (1512 kDa) to ultrahigh (7119 kDa), while maintaining narrow molecular weight distributions (PDI = 1.08-1.39). The self-assembly of these brush block copolymers to solid thin-films and their photonic properties were investigated. Due to the rigid architecture of these novel polymeric materials, they rapidly self-assemble through simple controlled evaporation to photonic crystal materials that reflect light from the ultra-violet, through the visible, to the near-infrared. The wavelength of reflectance is linearly related to the brush block copolymer molecular weight, allowing for predictable tuning of the band gap through synthetic control of the polymer molecular weight. A combination of scanning electron microscopy and optical modeling was employed to explain the origin of reflectivity.

Precise Synthesis of Clickable Poly(n-hexyl isocyanate)

Well-defined clickable poly(n-hexyl isocyanate) (PHIC) with an azido or alkyne end group as rod-like building block has been prepared by the living coordination polymerization using organotitanium catalysts. The obtained clickable PHIC was subjected to the Cu-catalyzed azide/alkyne cycloaddition for the synthesis of well-defined macromolecular architectures based on PHIC as a rod polymer, e.g., PHIC-b-poly(N-isopropyl acrylamide) as rod–coil block copolymer and 4-arm star PHIC as a rod star polymer. Additionally, PHIC-b-poly(l-lactide) and PHIC-b-poly(ε-caprolactone) as novel rod–coil block copolymers were respectively synthesized by the ring-opening polymerizations of l-lactide and ε-caprolactone initiated from hydroxyl end-functionalized PHIC. All products were characterized by 1H NMR spectroscopy, MALDI–TOF mass spectrometry, and size exclusion chromatography equipped with multiangle laser light scattering and viscosity detectors.

Chiroptical Properties of Graft Copolymers Containing Chiral Poly(n-hexyl isocyanate) as a Side Chain

Chiral poly(n-hexyl isocyanate) (PHIC) macromonomers were synthesized by living anionic polymerization of n-hexyl isocyanate (HIC) using the functional initiator sodium N-(4-vinylphenyl)benzamide (Na–4VPBA) in tetrahydrofuran (THF) at −98 °C. Polymerization was terminated by (S)-2-acetoxypropionyl chloride using pyridine as a catalyst. Initiator efficiency and aggregation behavior during polymerization were also studied. Chiral PHIC macromonomers with varying molecular weight (MW) were synthesized with a narrow molecular weight distribution (MWD). Graft copolymerization of the chiral PHIC macromonomers was performed in toluene at 80 °C under vacuum using free radical polymerization with a 2,2′-azobis(2-methylpropionitrile) (AIBN) initiator. Several experiments were performed to determine the optimum polymerization time for macromonomers and graft copolymers. Formation of the graft copolymer was confirmed using SEC–MALLS, 1H NMR, and circular dichroism (CD). CD spectra showed that graft copolymers adopted a conformation with opposite helical sense and a lower CD intensity as compared with chiral PHIC macromonomers.

POLYMERIZATION OF ALKYL ISOCYANATE CATALYZED BY LANTHANUM SCHIFF BASE COMPLEXES

Four Lanthanum Schiff-base complexes were synthesized,and the polymerizations of alkyl isocyanates were studied using these complexes as single component catalysts.Lanthanum Schiff-base complexes La(HSalen1～4)3 have been synthesized by metathesis reaction of anhydrous LaCl3 with Schiff-base sodium salts NaSalen.The complex La(HSalen2)3 with the formula of [3,5-tBu2-2-(O)C6H2CH=NC6H5]3La(THF) was characterized by X-ray diffraction,and the structure around Lanthanum center could be described as a pentagonal bipyramid.The polymerization of alkyl isocyanates was successfully carried out by using these complexes as single component catalysts,and the [OC6H2CH=NC6H5]3La(THF) complex(La(HSalen1)3) shows the highest catalytic activity to the polymerization of isocyanates.The influences of polymerization temperature,polymerization time,the concentration of catalyst and monomer,and the polymerization solvent on the polymerization of hexyl isocyanate(HIC) catalyzed by La(HSalen1)3 were investigated.It was found that under the polymerization conditions examined,PHIC can be prepared under-40℃～20℃ with complex La(HSalen1)3 as catalyst.Due to the depolymerization,higher reaction temperature leads to low polymer yield and molecular weight of PHIC obtained.Confirmed by GPC analysis,prolonging polymerization time is also in favor of depolymerization,the GPC profile of PHIC prepared after 12 h polymerization indicates the exist of dimmers and trimers.PHIC could be prepared with yield of 75.5%,number-average molecular weight(Mn) of 6.00×104and MWD of 3.86 under the following optimum conditions: = 3.43 mol/L,[La(HSalen1)3]= 8.58×10-3mol/L,polymerization at -40℃ for 12 h in toluene.

Correction to Molecular Weight Dependence of Surface Dilatational Moduli of Poly(n-hexyl isocyanate) Films Spread at the Air−Water Interface

ADVERTISEMENT RETURN TO ISSUEPREVAddition/CorrectionORIGINAL ARTICLEThis notice is a correctionCorrection to Molecular Weight Dependence of Surface Dilatational Moduli of Poly(n-hexyl isocyanate) Films Spread at the Air−Water InterfaceTakako Morioka*, Osamu Shibata, and Masami KawaguchiCite this: Langmuir 2011, 27, 2, 861Publication Date (Web):December 20, 2010Publication History Received29 November 2010Published online20 December 2010Published inissue 18 January 2011https://doi.org/10.1021/la1047529Copyright © 2010 American Chemical SocietyRIGHTS & PERMISSIONSArticle Views228Altmetric-Citations-LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (769 KB) Get e-AlertsSUBJECTS:Interfaces Get e-Alerts

Binding of Carboxylic Acids by Fluorescent Pyridyl Ureas

Fluorescent pyrid-2-yl ureas were prepared by treating halogenated 2-aminopyridines with hexyl isocyanate, followed by Sonogashira coupling with arylacetylenes. The sensors emit light of ∼360 nm with quantum yields of 0.05-0.1 in acetonitrile solution. Addition of strong organic acids (pK(a) < 13 in CH(3)CN) shifts the fluorescence band to lower energy, and clean isoemissive behavior is observed. Fluorescence response curves (i.e., F/F(0) vs [acid](total)) are hyperbolic in shape for CCl(3)COOH and CF(3)COOH, with association constants on the order of 10(3) M(-1) for both acids. (1)H NMR titrations and DFT analyses indicate that trihaloacetic acids bind in ionized form to the receptors. Pyridine protonation disrupts an intramolecular H-bond, thereby unfolding an array of ureido NH donors for recognition of the corresponding carboxylates. Methanesulfonic acid protonates the sensors, but no evidence for conjugate base binding at the urea moiety is found by NMR. An isosteric control compound that lacks an integrated pyridine does not undergo significant fluorescence changes upon acidification.

Molecular Weight Dependence of Surface Dilatational Moduli of Poly(n-hexyl isocyanate) Films Spread at the Air−Water Interface

The surface dilatational modulus of the monolayer of a well-known semiflexible polymer, poly(n-hexyl isocyanate) (PHIC), at the air-water interface was measured as a function of the molecular weight of PHIC. In the dilute regime, the surface dilatational modulus of PHIC showed a linear response over a measured strain range of 5%-20%. The modulus could be well-separated into the elastic component E' and the viscous component E'', irrespective of molecular weight of PHIC. The E' and E'' components, respectively, are mainly attributed to static compression modulus caused by a change in the area covered by the PHIC monolayer and the semiflexibility of the PHIC chain. In the semidilute regime, the surface dilatational modulus of PHIC showed a nonlinear response to even 1% of strain due to the semiflexibility of the PHIC chain. Moreover, the surface dilatational modulus of PHIC depended on its molecular weight: at the smaller strain, the surface dilatational modulus of the high molecular weight PHIC was larger than that of the low molecular weight PHIC. The surface dilatational modulus of the high molecular weight PHIC increased with the surface concentration, whereas that of the low molecular weight PHIC remained constant. The molecular weight dependence in the semidilute regime is caused by the difference in chain entanglement between the high and low molecular weight PHICs at the air-water interface.

Determination of isocyanates by capillary electrophoresis with tris(2,2′‐bipyridine)ruthenium(II) electrochemiluminescence

CE with tris(2,2'-bipyridyl) ruthenium(II) (Ru(bpy)(3) (2+)) electrochemiluminescence (ECL) detection for the quantitative determination of isocyanates was first reported. Hexamethylene diisocyanate (HDI) and hexyl isocyanate (HI) were used as the model analytes. Commercially available N,N-diethyl-N'-methylethylenediamine was used as the derivatization reagent. It has both a secondary amine group and a tertiary amine group. The secondary amine group can quantitatively react with isocyanate group, and the tertiary amine group can react with Ru(bpy)(3) (2+) to produce strong ECL signal for sensitive detection. The derivatization reaction was almost instantaneous and is much faster than other reported derivative reactions using other derivative reagents. The urea formed was stable. Linear calibration curve was obtained in the range from 0.01 to 10 microM for HDI, and 0.02 to 20 microM for hexyl isocyanate (HI). The detection limit is 0.01 microM for HDI and 0.02 microM for HI. The method is more sensitive than UV-detection and electrochemical detection. For practical application, recovery higher than 90% for HDI and HI was obtained for foam sample.

The Thiol−Isocyanate Click Reaction: Facile and Quantitative Access to ω-End-Functional Poly(N,N-diethylacrylamide) Synthesized by RAFT Radical Polymerization

N,N-Diethylacrylamide (DEAm) was homopolymerized by reversible addition−fragmentation chain transfer (RAFT) radical polymerization yielding a homopolymer with a calculated degree of polymerization of 30 (PDEAm30), as determined by 1H NMR spectroscopic end-group analysis, and a polydispersity index (Mw/Mn) of 1.10. Aminolysis of the dithioester end groups followed by treatment with tris(carboxyethyl)phosphine hydrochloride yielded the corresponding macromolecular secondary thiol (PDEAm30-SH). Reaction of PDEAm30-SH with a range of commercially available isocyanates, catalyzed by NEt3, gave the corresponding thiocarbamate end-functional polymers in essentially quantitative yield as determined by a combination of 1H NMR spectroscopy and UV−vis spectrophotometry. These reactions were shown to be rapid as evidenced by the real-time kinetics for the reaction between PDEAm30-SH and hexyl isocyanate in the presence of NEt3. Additionally, these facile reactions were shown to proceed without any apparent detrimental effect/side reactions to the basic polymer structure as evidenced by size exclusion chromatography with all modified polymers retaining their narrow molecular weight distributions. The lower critical solution temperatures (LCSTs) of the resulting ω-modified PDEAm homopolymers were evaluated by turbidimetry. For those samples that were soluble in aqueous media the measured LCSTs were between 3 and 11 °C lower than that determined for PDEAm30-SH (34 °C). Such differences were attributed to the hydrophobic nature of the newly introduced end groups—the effect being pronounced given the relatively low molecular weight of the precursor homopolymer. In two instances, and specifically the end-modified PDEAm homopolymers obtained from reaction with 9-isocyanato-9H-fluorene and 4-(2-isocyanatoethyl)biphenyl, the resulting materials were not soluble in water even at temperatures approaching 0 °C.

Block copolymers containing pyridine moieties: Precise synthesis and applications

This review highlights the precise synthesis and application of various well-defined rod–coil and coil–coil block copolymers composed of poly(2-(or 4-)vinylpyridine) (P2VP or P4VP) block(s) with pyridine moieties. These polymers were synthesized by means of living anionic polymerization. Poly(hexyl isocyanate) (PHIC) was used as the rod-like segment, because hexyl isocyanate undergoes living anionic polymerization under carefully selected conditions. This review describes the syntheses of the block copolymers, polystyrene- b-P2VP, polystyrene- b-P4VP, polyisoprene- b-P2VP, P2VP- b-poly(methyl methacrylate), P2VP- b-poly(ethylene oxide), P2VP- b-poly(2-( N-carbazolyl)ethyl methacrylate), P2VP- b-PHIC, P2VP- b-PHIC- b-P2VP, and PHIC- b-P2VP- b-PHIC. The formation of self-organized nanostructured materials and molecular assemblies by such block copolymers and their possible applications are also described. These assemblies include monolayers, microphase-separated periodic-ordered nanostructures, micelles, polymer–metal complexes, nanoparticles, inorganic and metal layers, and nanoporous films with nanoparticles.