Supramolecular Conformation Research Articles

Stimulation‐Reinforced Cellulose–Protein Ionogels with Superior Mechanical Strength and Temperature Resistance

AbstractIonogels, recognized for their flexibility and ionic conductivity, show considerable promise across various applications including electronic skins, biomedical electronics, and smart robotics. However, the majority of ionogels are plagued by suboptimal mechanical strength, a restricted range of operating temperatures, and poor recyclability. Here, an acetone‐stimulated supramolecular reinforcement strategy to develop robust and environmentally tolerant ionogels is introduced. The bio‐based ionogels feature a firm supramolecular architecture formed by the entwining of soybean protein molecules around cellulose macromolecular chains. This coiled design, inspired by cucumber vines, endows the ionogels with remarkable tensile strength (>30 MPa), enables them to withstand temperature above 85 °C with tensile strength over 15 MPa, and maintains notable cold resistance down to −20 °C with tensile strength exceeding 10 MPa. Further, the bio‐based ionogels exhibit excellent recyclability, reprocessing capabilities, shape customizability, good biocompatibility, and full biodegradability. This study provides a valuable strategy for manipulating supramolecular conformation to create robust ionogels that overcome the traditional trade‐offs of high strength and environmental tolerance.

A study of hydrophobic domain formation of polymeric drug precipitation inhibitors in aqueous solution

Despite the widespread use of polymers as precipitation inhibitors in supersaturating drug formulations, the current understanding of their mechanisms of action is still incomplete. Specifically, the role of hydrophobic drug interactions with polymers by considering possible supramolecular conformations in aqueous dispersion is an interesting topic. Accordingly, this study investigated the tendency of polymers to create hydrophobic domains, where lipophilic compounds may nest to support drug solubilisation and supersaturation. Fluorescence spectroscopy with the environment-sensitive probe pyrene was compared with atomistic molecular dynamics simulations of the model drug fenofibrate (FENO). Subsequently, kinetic drug supersaturation and thermodynamic solubility experiments were conducted. As a result, the different polymers showed hydrophobic domain formation to a varying degree and the molecular simulations supported interpretation of fluorescence spectroscopy data. Molecular insights were gained into the conformational structure of how the polymers interacted with FENO in solution phase, which apart from nucleation and crystal growth effects, determined drug concentrations in solution. Notable was that even at the lowest polymer concentration of 0.01 %, w/v, there were polymer-specific solubilisation effects of FENO observed and the resulting reduction in apparent drug supersaturation provided relevant knowledge both from a mechanistic and practical perspective.

The Surprising Nonlinear Effects of S100A9 Proteins in the Retina.

Age-related macular degeneration (AMD) is a complex disease in which inflammation is implicated as a key factor but the precise molecular mechanisms are poorly understood. AMD lesions contain an excess of the pro-inflammatory S100A9 protein, but its retinal significance was yet unexplored. S100A9 was shown to be intrinsically amyloidogenic in vitro and in vivo. Here, we hypothesized that the retinal effects of S100A9 are related to its supramolecular conformation. ARPE-19 cultures were treated with native dimeric and fibrillar S100A9 preparations, and cell viability was determined. Wild-type rats were treated intravitreally with the S100A9 solutions in the right eye and with the vehicle in the left. Retinal function was assessed longitudinally by electroretinography (ERG), comparing the amplitudes and configurations for each intervention. Native S100A9 had no impact on cellular viability in vitro or on the retinal function in vivo. Despite dispersed intracellular uptake, fibrillar S100A9 did not decrease ARPE-19 cell viability. In contrast, S100A9 fibrils impaired retinal function in vivo following intravitreal injection in rats. Intriguingly, low-dose fibrillar S100A9 induced contrasting in vivo effects, significantly increasing the ERG responses, particularly over 14 days postinjection. The retinal effects of S100A9 were further characterized by glial and microglial cell activation. We provide the first indication for the retinal effects of S100A9, showing that its fibrils inflicted retinal dysfunction and glial activation in vivo, while low dose of the same assemblies resulted in an unpredicted enhancement of the ERG amplitudes. These nonlinear responses highlight the consequences of self-assembly of S100A9 and provide insight into its pathophysiological and possibly physiological roles in the retina.

Shorter-chained trialkylsulfonium cations are preferable as admixtures to lithium-ion and sodium-ion electrolytes in acetonitrile

The development and improvement of electrolytes is a persisting research agenda in the context of electrochemical energy sources. The sodium-ion is a possible and partial substitute for Li-ion in alkali ion batteries of the future. Many large-scale applications urge electrolytes featuring a competitive interplay of ionic conductivity, shear viscosity, and cohesion energy. The general applicability of sulfonium ionic liquids (ILs) reinforced with Li-ions to energy storage was experimentally exemplified in recent years. Herein, we employed potential energy surface exploration bundled with electronic-structure simulations to shed light on the ion-ionic and ion-molecular interactions in perspective electrolyte systems involving trialkylsulfonium cation, Li/Na salts, and acetonitrile (ACN). By analyzing a wealth of supramolecular conformations and characterizing them via thermodynamics, structure, charge density distributions, electrostatic potential surfaces, atom–atom couplings, and reactivity descriptors, we outline the most promising sulfonium-based electrolytes. We provide a critical discussion of the future of sodium-ion batteries and compare them to lithium-ion batteries directly. The oxygen atoms of bis(trifluoromethanesulfonyl)imide anion [TFSI] coordinate Li+ and Na+ to remarkably various extents. Surprisingly, the size of the chosen trialkylsulfonium-based cation impacts the ion-ionic interactions weakly, contrary to expectations. Whereas the difference between the behavior of the Li-ion and Na-ion is paramount irrespective of all other components and their stationary points. [TFSI] was confirmed to be a highly flexible chemical structure although its conformations (one cis and two trans) were unraveled to differ only within an amount of thermal energy at room conditions. The reported discussion drives ongoing trials of the alkali-ion electrolytes based on sulfonium ILs and ACN.

A win-win scenario for antibacterial activity and skin mildness of cationic surfactants based on the modulation of host-guest supramolecular conformation

The commercial cationic surfactants (CSAa) with quaternary ammonium (QA) groups have proved to be broad-spectrum bactericide against bacteria, fungi, and viruses. Nevertheless, they inevitably exhibit potent irritation on the skin. In this work, we systematically investigated the regulatory mechanism of the host-guest supramolecular conformation with β-cyclodextrin (β-CD) on the bactericidal performance and skin irritation of CSAa with different head groups and chain lengths. When the ratio of incorporated β-CD is not greater than 1:1, the bactericidal efficiency of CSAa@β-CD (n > 12) remained above 90 % due to the free QA groups and hydrophobic fraction that can act on negatively charged bacterial membranes. And once the ratio of β-CD exceeded 1:1, the β-CD attracted to the bacterial surface by hydrogen bonding might prevent CSAa@β-CD from acting on bacteria, resulting in a decrement in antibacterial performance. Even so, the antibacterial activity of CSAa with long alkyl chains (n = 16, 18) was independent from the complexation of β-CD. Accordingly, both the zein solubilization assay and the neutrophil migration assay on zebrafish skin evidenced that β-CD attenuated the interaction of surfactant with skin model proteins and the inflammatory effect on zebrafish, thereby enhancing skin mildness. In this way, we hope to create a simple but effective brainpower using the host-guest approach to guarantee both bactericidal efficiency and skin mildness without modifying the chemical structure of these commercial biocides.

Synthesis and structure of polycyclic 1,2,3-triazolylmethyl-benzimidazole derivatives — Experimental and computational quantum chemical studies

Three novel triazolo-benzimidazolyl derivatives have been designed and efficiently synthesized via Cu-catalyzed azide-alkyne cycloaddition (CuAAC) reaction between the N-propargyl benzimidazole and diverse arylazides. Compounds (6a-c) were characterized by spectroscopic techniques (1H and 13C NMR) and the solid-state structure of derivative 6b was elucidated by X-ray crystallography. The compound crystallizes in the triclinic system with P-1 space group, as single molecule in the asymmetric unit. The supramolecular conformation is stabilized by miscellaneous network of intermolecular interactions, mainly C—H…N(O) H-bonds. The nature and energetics of key non-covalent interactions were analysed based on the Hirshfeld surface and further confirmed through Atoms-In-Molecules (AIM) topological technique. Moreover, Mappings of electrostatic potential (MEP) and Parr functions were used for the identification of the probable reactive sites.

A new 3D supramolecular Zn(II) compound: Crystal structure and important role in treatment of pulpitis

An innovative thermostable 2-D layered Zn(II) compound, chemical terms are written as [Zn(3-pysa)2(H2O)2]n (1, 3-Hpysa = 3-pyridinesulfonic acid), has been generated from the solvothermal reactions of 3-Hpysa and Zn(NO3)2·6H2O. Its single crystal analysis was implemented via the single crystal X-ray diffraction analysis together with the powder X-ray diffraction, elemental analysis and thermogravimetric analysis. The crystal framework is of monoclinic P21/n space group and its crystal cell figures: a = 7.7499(5), b = 10.9923(6), c = 8.3430(5) Å, α = 90, β = 96.924(6), γ = 90°, V = 705.55(7) Å3, Z = 4. The 2D layers were finally combined to a 3-D supramolecular conformation through intermolecular H-bonds existing between coordinated H2O molecules and sulfonate oxygen atoms from adjacent layer. Its practical role in pulpitis treatment was estimated and the relevant mechanism was studied in the meantime.

A unique multidrug nanomedicine made of squalenoyl-gemcitabine and alkyl-lysophospholipid edelfosine

Among anticancer nanomedicines, squalenoyl nanocomposites have obtained encouraging outcomes in a great variety of tumors. The prodrug squalenoyl-gemcitabine has been chosen in this study to construct a novel multidrug nanosystem in combination with edelfosine, an alkyl-lysophopholipid with proven anticancer activity. Given their amphiphilic nature, it was hypothesized that both anticancer compounds, with complementary molecular targets, could lead to the formation of a new multitherapy nanomedicine. Nanoassemblies were formulated by the nanoprecipitation method and characterized by dynamic light scattering, transmission electron microscopy and X-ray photoelectron spectroscopy. Because free edelfosine is highly hemolytic, hemolysis experiments were performed using human blood erythrocytes and nanoassemblies efficacy was evaluated in a patient-derived metastatic pediatric osteosarcoma cell line. It was observed that these molecules spontaneously self-assembled as stable and monodisperse nanoassemblies of 51 ± 1 nm in a surfactant/polymer free-aqueous suspension. Compared to squalenoyl-gemcitabine nanoassemblies, the combination of squalenoyl-gemcitabine with edelfosine resulted in smaller particle size and a new supramolecular conformation, with higher stability and drug content, and ameliorated antitumor profile.

PBTTT-C16 sol-gel transition by rod associations and networking.

A low-molecular-weight poly(2,5-bis(3-hexadecylthiophen-2-yl)thieno[3,2-b]thiophene) (designated as Lw-pBTTT-C16) in a fair solvent (chlorobenzene, CB) displays peculiar structural, mechanical, and electronic features during sol-gel transition. Using comprehensive (multiscale) dynamic/static analysis schemes, the Lw-pBTTT-C16/CB solution (10 mg mL-1) is shown to capitalize on rod associations and networking to form a gel, in stark contrast with its high-molecular-weight companion previously reported to form gels through hierarchical colloidal bridging. The present study reveals, however, that the molecular weight of pBTTT-C16 has a subtle impact on the gelation behaviors through the rarely recognized, contrasting supramolecular conformations (rod-like vs. wormlike) of the aggregate clusters fostered in the pristine solution. The ac conductivity nearly doubles as a result of improved (mesoscale) packing of cylindrical aggregates near the gel state as well as enhanced backbone rigidity of the constituting chains. Other distinguishing features include: (1) there is no real crossover of the dynamic moduli (G' and G'') upon increasing the temperature from gel (T = 15 °C) to solution (T = 80 °C) states. (2) The gel is about a hundredfold softer in dynamic modulus, yet more resilient with a fivefold increase in the yield strain. Both viscoelastic features are expected to greatly benefit the gel processability. (3) The coexistent microgels and cylinder (aggregate) bundles form a peculiar gel network that has not been reported previously with polymer or colloidal gels. The overall findings provide new mechanistic insight into the phenomenological effects of molecular weight for the pBTTT-Cn series in solution, sol, gel, and thin film.

Helical screw sense bias in chiral polyfluorene stimulated by solvent.

Conjugated homopolymer poly(9,9-bis(3-((S)-2-methylbutylpropanoate))fluorene) (PSF) with chiral pendants was synthesized and characterized. Dissolution experiments show that PSF is well dissolved in racemic limonene at high temperature and begins aggregating upon sequential cooling treatment. The corresponding assemblies were transferred to quartz plate by the spin-coating method. Comparably, film casting from chloroform solution was also prepared. Upon annealing thermal treatments, these PSF films exhibited perfect mirror circular dichroism (CD) Cotton effects and dissymmetry ratios. Optical absorption spectroscopy (UV-vis), CD, and fluorescence spectroscopy results reveal that chiral side chains successfully induced M- and P-helical structures in aggregates and films, and this significant difference was ascribed to their differential supramolecular conformations.

Nanoporosity, Inclusion Chemistry, and Spin Crossover in Orthogonally Interlocked Two-Dimensional Metal-Organic Frameworks.

[Fe(tvp)2 (NCS)2 ] (1) (tvp=trans-(4,4'-vinylenedipyridine)) consists of two independent perpendicular stacks of mutually interpenetrated two-dimensional grids. This uncommon supramolecular conformation defines square-sectional nanochannels (diagonal≈2.2 nm) in which inclusion molecules are located. The guest-loaded framework 1@guest displays complete thermal spin-crossover (SCO) behavior with the characteristic temperature T1/2 dependent on the guest molecule, whereas the guest-free species 1 is paramagnetic whatever the temperature. For the benzene-guest derivatives, the characteristic SCO temperature T1/2 decreases as the Hammet σp parameter increases. In general, the 1@guest series shows large entropy variations associated with the SCO and conformational changes of the interpenetrated grids that leads to a crystallographic-phase transition when the guest is benzonitrile or acetonitrile/H2 O.

Functional carbazole liquid-crystal block codendrimers with optical and electronic properties.

The synthesis and characterisation of a family of block codendrimers consisting of highly versatile mesogenic and carbazole-containing 2,2-bis(hydroxymethyl)propionic acid (bis-MPA) dendrons are reported. The liquid-crystal behaviour was investigated by means of differential scanning calorimetry, polarised-light optical microscopy and X-ray diffraction. Depending on the chemical structure of the constituent dendrons, the codendrimers show lamellar or columnar mesophases. On the basis of the experimental results, models both at the molecular level and in the mesophase are proposed. The physical properties of the block codendrimers derived from the presence of the carbazole moiety in their structure were investigated: photoluminescence in solution and in the mesophase, electrochemical behaviour and hole transport. Electrodeposition of carbazole dendrons afforded a globular supramolecular conformation in which the mesogenic molecular side plays a key role.

Notable lattice deformation in a solid copper(II) dicyanamide complex induced by temperature-dependent supramolecular conformation

A solid copper complex with a dimer unit as the building block is assembled through two different hydrogen bonding interactions and features two types of deformable supramolecular rings. As a result, a notable lattice deformation can be observed upon thermal stimulus, owing to the temperature-dependent supramolecular conformation. In addition, its variable-temperature dielectric property was also investigated.

Demonstrating the importance of polymer-conjugate conformation in solution on its therapeutic output: Diethylstilbestrol (DES)-polyacetals as prostate cancer treatment

The design of improved polymeric carriers to be used in the next generation of polymer therapeutics is an ongoing challenge. Biodegradable systems present potential advantages regarding safety benefit apart from the possibility to use higher molecular weight (Mw) carriers allowing PK optimization, by exploiting the enhanced permeability and retention (EPR)-mediated tumor targeting. Within this context, we previously designed pH-responsive polyacetalic systems, tert-polymers, where a drug with the adequate diol-functionality was incorporated within the polymer mainchain. The synthetic, non-steroidal estrogen, diethylstilboestrol (DES) clinically used for the treatment of advanced prostate cancer was chosen as drug. In order to improve the properties of this tert-polymer, novel polyacetalic systems as block-co-polymers, with more defined structure have been obtained. This second generation polyacetals allowed higher drug capacity than the tert-polymer, a biphasic DES release profile at acidic pH and due to its controlled amphiphilic character readily formed micelle-like structures in solution. These features result in an enhancement of conjugate therapeutic value in selected prostate cancer cell models. Exhaustive physico-chemical characterization focusing on nanoconjugate solution behavior and using advanced techniques, such as, pulsed-gradient spin-echo NMR (PGSE-NMR) and small-angle neutron scattering (SANS), has been carried out in order to demonstrate this hypothesis. Clear evidence of significantly different conformation in solution has been obtained for both polyacetals. These results demonstrate that an adequate control on molecular or supramolecular conformation in solution with polymer therapeutics is crucial in order to achieve the desired therapeutic output.

1:2 and 2:1 Stoichiometric Inclusion Complexes of 1,1,6,6-Tetraphenylhexa-2,4-diyne-1,6-diol and p-Anisaldehyde

1:2 and 2:1 stoichiometric complexes of 1,1,6,6-tetraphenylhexa-2,4-diyne-1,6-diol (DD) and p-anisaldehyde were presented in this paper. 2:1 inclusion complex of DD with p-anisaldehyde (denote 1) was fortuitously obtained from the volatile oil of medicine herb Zanthoxylum schinifolium Sieb.et Zucc. 1:2 inclusion complex of DD with p-anisaldehyde (denote 2) was obtained under ordinary crystallization conditions. The results of single crystal X-ray diffraction show that complex 1 is triclinic, space group Pī, whereas the complex 2 is monoclinic, space group P21/n. In the complex of 1, 1D zigzag ribbon host framework is constructed through a closed hydrogen bonding network formed by DD molecules themselves and p-anisaldehyde molecules are accommodated into the tunnel enclosed by 1D zigzag ribbons. In the complex of 2, DD and p-anisaldehyde are connected with each other via hydrogen bonding, forming a layer-type structure. DD molecule exhibits gauche conformation in complex 1 and antiperiplanar conformation in complex 2, which are regarded as supramolecular conformation stereoisomers. 1:2 and 2:1 stoichiometric complexes (1 and 2) of 1,1,6,6-tetraphenylhexa-2,4-diyne-1,6-diol (DD) and p-anisaldehyde were presented in this study. DD molecule exhibits gauche conformation in complex 1 and antiperiplanar conformation in complex 2, which are regarded as supramolecular conformation stereoisomers.

Morphology, size distribution, and aggregate structure of lipopolysaccharide and lipid A dispersions from enterobacterial origin

Lipopolysaccharides (LPSs) from Gram-negative bacteria are strong elicitors of the human immune systems. There is strong evidence that aggregates and not monomers of LPS play a decisive role at least in the initial stages of cell activation of immune cells such as mononuclear cells. In previous reports, it was shown that the biologically most active part of enterobacterial LPS, hexa-acyl bisphosphorylated lipid A, adopts a particular supramolecular conformation, a cubic aggregate structure. However, little is known about the size and morphology of these aggregates, regarding the fact that LPS may have strong variations in the length of the saccharide chains (various rough mutant and smooth-form LPS). Thus, in the present paper, several techniques for the determination of details of the aggregate morphology such as freeze-fracture and cryo-electron microscopy, analytical ultracentrifugation, laser backscattering analysis, and small-angle X-ray scattering were applied for various endotoxin (lipid A and different LPS) preparations. The data show a variety of different morphologies not only for different endotoxins but also when comparing different applied techniques. The data are interpreted with respect to the suitability of the single techniques, in particular on the basis of available literature data.

Structural and Functional Modifications of the Major Light-Harvesting Complex II in Cadmium- or Copper-Treated Secale cereale

The effects of 50 microM cadmium (Cd) or copper (Cu) ions on the supramolecular conformation of the light-harvesting pigment-protein complex of PSII (LHCII) isolated from rye seedlings were studied. It was found that the action of these two metal ions on the LHCII structure and organization is dissimilar. The Fourier transform infrared (FTIR) measurements indicated inhibition or stimulation of formation of parallel beta-structures and aggregates in the presence of Cd or Cu ions, respectively. The Chl a fluorescence excitation spectra of LHCII extracted from Cd-treated plants showed that the decreased aggregation of complexes was correlated with a decline in efficiency of quenching of excitation energy. From the results of mass spectrometry, changes in LHCII aggregation in the presence of Cd ions might be based on decreases in the molecular mass of Lhcb1 and Lhcb2 proteins. An increase in the content of LHCII aggregates under Cu ion excess was associated with changes in the LHCII xanthophyll pigment pool. In the complexes isolated from Cu-treated plants, all-trans violaxanthin and 9'-cis neoxanthin content declined and the simultaneous appearance of the fraction of 9-cis violaxanthin was observed. 9-cis violaxanthin formation under Cu ion excess might facilitate LHCII inter-trimer interaction and, therefore, aggregation of complexes. RLS (resonance light scattering) spectra indicated that the excitonic interaction between Chl molecules and between Chls and xanthophylls was responsible for the effective dissipation of excitation energy in LHCII isolated from Cu-treated plants. Also, changes in singlet excitation energy transfer between carotenoids and Chls under the action of heavy metals were observed.

Conformational Polymorph of o‐Aminoanilinium(dibenzo[18]crown‐6) Supramolecules in [Ni(dmit)2]− Salts

The supramolecular (HOPD(+))(DB[18]crown-6) cation, in which HOPD(+) and DB[18]crown-6 are o-aminoanilinium and dibenzo[18]crown-6, respectively, was introduced into [Ni(dmit)(2)](-) salts (dmit(2-) = 2-thioxo-1,3-dithiole-4,5-dithiolate). Conformational polymorphs were observed as tetragonal (HOPD(+))(DB[18]crown-6)[Ni(dmit)(2)](-) (1) and monoclinic (HOPD(+))(DB[18]crown-6)[Ni(dmit)(2)](-) (2). The ammonium group of HOPD(+) in salts 1 and 2 formed the N-H(+)O hydrogen bonds at the bottom and upper positions of V-shaped DB[18]crown-6, respectively, thereby producing a different supramolecular conformation. The [Ni(dmit)(2)](-) anion arrangements in salts 1 and 2 were 4(1)-helical pi stacking and a two-dimensional layer, respectively, depending on the conformation of the supramolecular cations. The magnetic behavior of salts 1 and 2 obeyed the Curie-Weiss law at room temperature with S = 1/2 spin on the [Ni(dmit)(2)](-) anion. However, the g value and line width in the electron resonance spectra of salt 1 showed a magnetic anomaly at 28 K, which was owing to antiferromagnetic ordering in the 4(1)-helical [Ni(dmit)(2)](-) pi stack. Large temperature- and frequency-dependent dielectric responses were observed for salt 2 at temperatures above 200 K, whereas no particular dielectric responses were observed in salt 1. The molecular motion of HOPD(+) within the cationic layer of salt 2 contributed to the dielectric response, and this was supported by ab initio calculations showing the potential-energy curve for pendulum motion and by the large thermal parameters in the X-ray crystal structure analysis. The fixed (HOPD(+))(DB[18]crown-6) arrangement in the crystal of salt 1 was consistent with the small dielectric response. The steric hindrance of the o-amino group of HOPD(+) in the supramolecular cation structure yielded the conformational polymorph with different dielectric and magnetic properties.

Optical Anisotropy of Supported Lipid Structures Probed by Waveguide Spectroscopy and Its Application to Study of Supported Lipid Bilayer Formation Kinetics

Supramolecular conformation and molecular orientation was monitored during supported lipid bilayer (SLB) formation using dual polarization interferometry (DPI). DPI was shown to enable real time sensitive determination of birefringence of the lipid bilayer together with thickness or refractive index (with the other a fixed value). This approach removes differences in mass loading due to anisotropy, so the mass becomes solely a function of the lipid d n/d c value. DPI measurements show highly reproducible qualitative and quantitative results for adsorption of liposomes of different lipid compositions and in buffers with or without CaCl 2. The packing of solvent-free self-assembled SLBs is shown to differ from other preparation methods. Birefringence analysis accompanied by mass and thickness measurements shows characteristic features of vesicle adsorption and SLB formation kinetics previously not demonstrated by evanescent optical techniques, including indications of percolation-type rupture of clusters of liposomes on the surface and correlated adsorption kinetics induced by liposome charge repulsion. Our study demonstrates that understanding of mechanistic details for an adsorption process for which conformational changes and ordering occur can be elucidated using DPI and greatly enhanced by modeling of optical birefringence. The data is in some respects more detailed than what can be obtained with conventional biosensing techniques like surface plasmon resonance and complementary to methods such as the quartz crystal microbalance.

Synthesis by oxidative polymerization of optically active, regioregular polythiophene from quinquethiophene monomer bearing chiral and n-dodecyl groups as substituents

AbstractThe synthesis and characterization of an optically active quinquethiophene monomer 3,3””-didodecyl-4’,3”’-di[(S)-(+)-2-methylbutyl]- 2,2’:5’,2”:5”,2”’:5”’,2””-quinquethiophene [(S)-(+)-DDDMBQT], bearing at the C-β positions of thiophene rings both linear C12 alkyl chain and chiral, enantiomerically pure, alkyl group is described. The polymerization of [(S)-(+)-DDDMBQT] by oxidative mechanism has been optimized in terms of yield of soluble polymer with high molecular weight.The obtained polymeric derivative displays enhanced conjugation extension with respect to similar poly(3-alkylthiophene)s reported in the literature and optical activity in the spectral region related to the chromophore absorptions when in the microaggregate state, indicative of the presence of supramolecular chiral conformations.