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Precise snake venom identification is the prerequisite for clinical treatment, production of antiserum, basic research, and other applications. Unfortunately, it is still a challenging task which mainly originates from their extraordinary complicated protein composition. Differential sensing strategy was applied benefiting from its advantage in discrimination of complex mixtures. Herein, A dual-mode supramolecular fluorescent sensor array based on the heteromultivalent sensing strategy was developed. The heteromultivalent macrocyclic coassemblies with strong and pan-selective binding to proteins were employed to construct sensor units. Fluorescence intensity and anisotropy signals were integrated, which were expected to show multidimensional information of proteins, such as surface groups, protein structures, and molecular weights. Finally, a supramolecular sensor array with the ability of facile, rapid and general species-specific identification and taxonomic classification for snake venom was constructed. The sensor array also demonstrated its advantage in semiquantitative analysis and multi-level identification, suggesting its great potential for practical use. [ABSTRACT FROM AUTHOR]

This perpective delves into the emerging field of matere bonds, a novel type of noncovalent interaction involving group 7 elements such as manganese, technetium, and rhenium. Matere bonds, a new member of the σ-hole family where metal atoms act as electron acceptors, have been shown experimentally and theoretically to play significant roles in the self-assembly and stabilization of supramolecular structures both in solid-state and solution-phase environments. This perspective article explores the physical nature of these interactions, emphasizing their directionality and structural influence in various supramolecular architectures. Recent studies have expanded the understanding of matere bonds beyond classical metal–ligand coordination, highlighting their potential in crystal engineering and catalysis. This perspective article also examines the occurrence of matere bonds in biological systems, particularly within manganese-containing proteins, where they contribute to the structural integrity and catalytic activity. Theoretical and computational analyses, including molecular electrostatic potential surfaces and density functional theory, further elucidate the properties and applications of matere bonds, offering new insights for the design of advanced materials and biomimetic systems. This comprehensive overview underscores the versatility of matere bonds, paving the way for future innovations in supramolecular chemistry involving metals. [ABSTRACT FROM AUTHOR]

Nanostructured surface-specific supramolecular chemistry refers to the process of functional assembly on nanomaterial surfaces through non-covalent specific interactions, as well as the recognitions or interactions between the modified nanomaterials and target molecules or active sites. This process exemplifies the principles of green chemistry by reducing the use of hazardous chemicals, minimizing waste, and promoting energy-efficient synthesis in the construction of functional nanomaterials for biomedical applications. Over the past five years, nanostructured surface-specific supramolecular chemistry has made significant progress in the field of biomedical engineering, particularly in drug delivery, diagnostics, biosensing, and therapy. Through host–guest assembly, nucleic acid recognition, and interactions between proteins/peptides and target molecules, these systems achieve precise control over the functional performance of nanomaterials. The flexibility of supramolecular techniques allows for a high degree of customization in various biomedical applications, such as cancer treatment, immunotherapy, and real-time diagnostics. This review focuses on recent advancements in the design and applications of these systems, summarizing the green chemistry principles they embody during their construction and application, and identifying future research directions and challenges faced by this field. [ABSTRACT FROM AUTHOR]

Noble gas bonding (NgB) is a noncovalent interaction where noble gases, such as xenon or krypton, function as Lewis acids. These interactions arise from regions of positive electrostatic potential, known as σ-holes or π-holes, which form on the noble gas atom and interact with electron-rich sites, such as lone pairs or anions. Although recently discovered, NgBs have demonstrated considerable potential in supramolecular chemistry, with their strength—especially in the case of heavier noble gases like xenon—comparable to that of hydrogen bonds. Anion⋯anion interactions, which are typically hindered by electrostatic repulsion, can occur through attractive forces like σ-hole and π-hole interactions. While these interactions are increasingly observed in biological and synthetic systems, particularly in solid-state and polar environments, their stabilization via NgBs remains largely unexplored. In this study, we present a computational and experimental analysis of noble gas bonds (NgBs) facilitating anion⋯anion interactions, emphasizing the unique role of xenon as a σ-hole donor. Through a combination of Cambridge Structural Database (CSD) inspection and density functional theory (DFT) calculations, we reveal the novel contribution of NgBs in dispersing electrostatic charge, allowing for the stabilization of anion⋯anion dimers. Our findings suggest that, while the concept of counterion-mediated anion⋯anion attraction is well known, the use of noble gas bonding offers a distinct and previously unexplored mechanism for enabling such interactions. These results open new possibilities for designing supramolecular assemblies with unconventional bonding motifs. [ABSTRACT FROM AUTHOR]

Affinity proteins based on a three-helix bundle (affibodies, alphabodies, and computationally de novo designed ones) have been shown to be a general platform to discover binders with properties reminiscent of antibodies, combining high target specificity with affinities reaching well below the nanomolar. Herein, we report a strategy, coined self-assembled proteomimetic (SAP), to mimic such three-helix bundle architecture with a hybridization-enforced two-helix coiled coil that is obtained by templated native chemical ligation (T-NCL) of PNA-peptide conjugates. This SAP strategy stands out by its synthetic accessibility, reducing the length on the longest synthetic peptide to less than 30 amino acids which is readily attainable by standard SPPS methodologies. We show that the T-NCL dramatically accelerates the ligation, enabling this chemistry to proceed in a combinatorial fashion at low micromolar concentrations. We demonstrate that small combinatorial libraries of SAPs can be prepared in one operation and used directly in affinity selections against a target of interest with an LC-MS analysis of the fittest binders. Moreover, we show that the underlying design paradigm is functional for SAPs based on structurally distinct three-helix peptides aimed at different therapeutic targets, namely HER2 and spike's RBD, reaching picomolar affinities. We further illustrate that the affinity of the SAP can be allosterically regulated using a toehold displacement of the hybridizing PNAs to disrupt the coiled coil stabilization. Finally, we show that an RBD-targeting SAP effectively inhibits viral entry of SARS-CoV-2 with an IC50 of 2.8 nM. [ABSTRACT FROM AUTHOR]

In this study, perfluoroalkylated derivatives of benzoic acid S-6 and O-6 were designed and synthesized as supramolecular gelators using a simple one-step method. Both S-6 and O-6 could form gels in various organic solvents. Notably, these compounds have potential applications in environmental remediation, with S-6 demonstrating significant promise for oil spill treatment. After five recycling cycles, the recovery rate of the gelation capacity for diesel oil remained above 90%. Xerogels derived from O-6 at a concentration of 5 wt% in pump oil effectively adsorbed Rhodamine B (RhB). The adsorption process primarily involved chemical adsorption, electrostatic interactions between the O-6 xerogel and the cationic RhB dye, as well as physical adsorption within the xerogel's pores. In summary, benzoic acid derivatives represent a kind of multifunctional, recyclable, and efficient materials. [ABSTRACT FROM AUTHOR]

The birth and development of supramolecular chemistry have heralded a new era, where macrocycles have become an irreplaceable research tool. Therefore, the construction of novel macrocycles has become a hot spot. Tröger's base (TB), as a fragment with both rigidity and chirality, promises tremendous potential in the realm of supramolecular chemistry, and its unique properties continue to motivate researchers to explore its inclusion in macrocycles. However, the construction of a TB-embedded macrocycle is always difficult due to the frequent occurrence of excessive tension. For successful synthesis, part of the function of TB in macrocycle is often overlooked or sacrificed to facilitate the macrocyclization process, leading to serious deficiencies in the utilization of the functions of TB. Thus, the research on TB-embedded macrocycles is still in its preliminary stage. Hence, in this review, TB-embedded macrocycles are highlighted, focusing not only on the linkers of these macrocycles but also on the correlation between the properties of TB and TB-embedded macrocycles. We hope that this review will further guide the synthesis of more excellent macrocycles. [ABSTRACT FROM AUTHOR]

AbstractTopological polymers and entangled polymer networks have emerged as highly versatile platforms for drug delivery, offering improved encapsulation efficiency, controlled release and biocompatibility. Unlike conventional linear polymers, these advanced macromolecular architectures, including cyclic polymers, polyrotaxanes, catenanes and interpenetrating polymer networks (IPNs), exhibit unique molecular entanglements and supramolecular interactions that enhance drug stability and prolong therapeutic effects. Their ability to undergo stimuli-responsive transformations allows for site-specific drug delivery, minimizing systemic side effects and improving patient outcomes. This review explores the fundamental principles of topological polymers and entangled networks, discussing their design strategies, rheological properties and encapsulation mechanisms. We highlight key biomedical applications, including their use in cancer therapy, gene delivery and regenerative medicine, emphasizing how these materials improve drug bioavailability and controlled diffusion. Future research must focus on enhancing polymer biodegradability, fine-tuning release kinetics and integrating real-time drug monitoring systems. By leveraging interdisciplinary approaches from macromolecular physics, supramolecular chemistry and pharmaceutical sciences, topological polymer-based drug delivery systems hold great promise in revolutionizing precision medicine. [ABSTRACT FROM AUTHOR]

Aromatic belts, ultrashort carbon nanotubes, and related structures, are emerging molecular entities in the fields of organic electronics and supramolecular chemistry owing to their structural rigidity, fully fused π-conjugation, and well-defined cavity. Synthesis of aromatic belts with embedded thiophene structures, which manifest significant optoelectronic and conductive properties, has not yet been achieved. Herein, we report the synthesis of thiophene-fused aromatic belts (thiophene belts) via one-step sulfur cross-linking reaction of partially fluorinated cycloparaphenylenes. Their structural features, including unidirectional columnar stacking with high dipole moment in crystals, two-dimensional layer assembly on metal surfaces, and photophysical properties, such as long-lifetime phosphorescence, are uncovered. These distinctive features of the thiophene belts should inspire a range of applications such as optoelectronic devices and polar materials. Synthesis of aromatic belts with embedded thiophene structures, which manifest significant optoelectronic and conductive properties, has not yet been achieved. Herein, the authors report the synthesis of thiophene-fused aromatic belts via one-step sulfur cross-linking reaction of partially fluorinated cycloparaphenylenes. [ABSTRACT FROM AUTHOR]

Metal–organic cages (MOCs) are discrete supramolecular entities consisting of metal nodes and organic connectors or linkers; MOCs are noted for their high porosity and processability. Chemically, they can be post-synthetically modified (PSM) and new functional groups can be introduced, presenting attractive qualities, and it is expected that their new properties will differ from those of the original compound. This is why they are highly regarded in the fields of biology and chemistry. The present review deals with the current PSM strategies used for MOCs, including covalent, coordination, and noncovalent methods and their structural benefits. The main emphasis of this review is to show to what extent and under what circumstances a MOC can be designed to obtain a tailored geometric architecture. Although sometimes unclear when examining supramolecular systems, particularizing the design of and systematic approaches to the development and characterization of families of MOCs provides new insights into structure–function relationships, which will guide future developments. [ABSTRACT FROM AUTHOR]

Pillar[n]arenes are a relatively new family of macrocyclic molecular hosts, consisting of methylene-linked phenol-based monomers attached in a para-substituted configuration. The macrocyclic nature of these molecules provides a well-defined internal cavity, into which smaller guest molecules can be included to form supramolecular host-guest inclusion complexes. The para-oriented attachment yields relatively rigid cylindrical or pillar-like molecular and cavity shapes, hence the name. In addition to the unique shape of these cavities (compared to the related meta-substituted calixarenes, for example), the aromatic nature of the cavity walls also contributes to distinctive host properties of pillar[n]arenes and guest affinities. Neutral pillar[n]arenes, such as those with alkyl substituents, are generally insoluble in water, and thus their host properties are studied in nonaqueous media. This review article will provide a comprehensive summary of the reported host binding studies of pillar[n]arenes in nonaqueous solution. A wide range of specific pillar[n]arenes have been studied in this way, as have a wide variety of sizes and types of guests. The emphasis will be on studies in which the value of the binding association constant Ka was measured and reported, to consider the effect of guest size, shape, and nature and the host size and substituents on the binding ability of pillar[n]arenes. The main objective of the paper is to provide a summary and overview of the host binding abilities of this fascinating family of molecular hosts in nonaqueous solution. [ABSTRACT FROM AUTHOR]

Macrocyclic structures are popular in supramolecular chemistry and have enjoyed considerable success as platforms for elaboration to container compounds and new materials. Host/guest studies in organic media have relied heavily on structures derived from crown ethers, calixarenes, cucurbiturils, resorcinarenes and pillararenes over the past decades. More recently, their water-soluble versions have been developed for potential applications in biology. Inspired by nature and the need for large-sized containers, Cao and co-workers have designed and synthesized a series of novel macrocyclic hosts based on the tetraphenylethylene (TPE) platform. These compounds have cationic frameworks with well-defined hydrophobic cavities for recognition of biomolecules (e.g. amino acids, nucleosides, peptides, proteins, coenzyme factors) in water. They offer multiple adaptive responses as sensors through fluorescence, circular dichroism and circularly polarized luminescence. These TPE-based hosts also show promising applications as stimuli-responsive fluorescent materials, in drug delivery and as artificial photofunctional systems. Herein, this review highlights this work as it establishes a new class of biomimetic, water-soluble supramolecular macrocyclic hosts. [ABSTRACT FROM AUTHOR]

In the evolving landscape of biomolecular supramolecular chemistry, recent studies on phenylalanine (Phe) have revealed important insights into the versatile nature of this essential aromatic amino acid. Phe can spontaneously self-assemble into fibrils with amyloid-like properties linked to the neurological disorder phenylketonuria (PKU). Apart from its pathological implications, Phe also displays complex phase behavior and can undergo structural changes in response to external stimuli. Its ability to co-assemble with other amino acids opens up new possibilities for studying biomolecular interactions. Furthermore, Phe's coordination with metal ions has led to the development of enzyme-mimicking catalytic systems for applications in organic chemistry, environmental monitoring, and healthcare. Research on L and D enantiomers of Phe, particularly on bio-MOFs, has highlighted their potential in advanced technologies, including bioelectronic devices. This review provides a comprehensive overview of the advancements in Phe-based supramolecular assemblies, emphasizing their interdisciplinary relevance. The Phe assemblies show great potential for future therapeutic and functional biomaterial developments, from disease treatments to innovations in bionanozymes and bioelectronics. This review presents a compelling case for the ongoing exploration of Phe's biomolecular supramolecular chemistry as a fundamental framework for developing sustainable and efficient methodologies across various scientific disciplines. [ABSTRACT FROM AUTHOR]

Noncovalent interactions encompass hydrogen bonding, electrostatic interactions, hydrophobic effects, n-n interactions, and van der Waals forces, among others. Despite being weaker than covalent bonds, these interactions pervade our daily lives, showcasing their significant influence at every moment. This article adopts a conversational format to briefly introduce everyday phenomena and objects driven by noncovalent interactions. Through practical examples, we aim to deepen readers' knowledge and understanding of the field of supramolecular chemistry, allowing the public to appreciate the marvels of molecular art within supramolecular chemistry. [ABSTRACT FROM AUTHOR]

The importance of anions in various processes has led to a search for molecules that can effectively recognize and interact with these anions. This study explores how the tetraglycine [(Gly)4] peptide in its zwitterionic, neutral, and terminally capped forms acts as a receptor for H2PO4− and HSO4− anions within the framework of supramolecular host‐guest chemistry. Using molecular dynamics (MD) simulations, we obtained the conformations of the receptor‐anion complexes. Density functional theory (DFT), quantifies the complexes' interaction energies in both gas and solvent phases. Proton transfer within the zwitterionic complex with H2PO4− anion alters peptide charge distribution, affecting its conformation and binding site arrangement, as analysed by quantum mechanics/molecular mechanics (QM/MM) methods. Symmetry‐adapted perturbation theory (SAPT) and noncovalent interactions analysis highlight the role of electrostatic interactions in these receptor‐anion complexes. It emphasizes the key interactions such as N−H⋅⋅⋅⋅O and O−H⋅⋅⋅O=C between the peptide backbone and anions and elucidates the molecular recognition mechanism driven by crucial noncovalent interactions. The termination of the peptide's end groups modulates anion binding sites from the backbone to the charged N‐terminal, resulting in distinct binding sites. Our findings provide insights for designing peptides tailored to function as anion receptors in diverse supramolecular chemistry applications. [ABSTRACT FROM AUTHOR]

The Mpox virus (MPXV) has emerged as a formidable orthopoxvirus, posing an immense challenge to global public health. An understanding of the regulatory mechanisms of MPXV infection, replication and immune evasion will benefit the development of novel antiviral strategies. Despite the involvement of G-quadruplexes (G4s) in modulating the infection and replication processes of multiple viruses, their roles in the MPXV life cycle remain largely unknown. Here, we found a highly conservative and stable G4 in MPXV that acts as a positive regulatory element for viral immunodominant protein expression. Furthermore, by screening 42 optically pure chiral metal complexes, we identified the Λ enantiomer of a pair of chiral helical compounds that can selectively target mRNA G4 and enhance expression of the 39-kDa core protein encoded by the MPXV A5L gene. Mechanistically, RNA G4-specific helicase DHX36 inhibits A5L protein expression by unwinding G4s. In contrast, MH3 Λ enhanced mRNA stability by specifically targeting G4 structures and subsequently increased protein expression. Furthermore, given the pivotal role of the 39-kDa core protein in activating immune responses and facilitating virion maturation, modulation of MPXV G4 folding by MH3 Λ exhibited inhibitory effects on MPXV replication through enhancing the immune response. Our findings underscore the critical involvement of G4 in the MPXV life cycle and offer potential avenues for developing antiviral drugs that target G4. [ABSTRACT FROM AUTHOR]

The amplification of asymmetry in supramolecular polymers has recently garnered significant attention. While asymmetry amplification has predominantly been explored under thermodynamic conditions, the kinetic aspect of this process unveils intriguing observations, yet is scarcely reported in the literature. Herein, drawing inspiration from macromolecular systems, we propose a novel strategy for enhancing asymmetry in supramolecular polymers through a seed‐induced supramolecular polymerization approach under kinetic conditions, employing a naphthalene diimide‐derived monomer (ANSG) for template‐induced supramolecular polymerization, utilizing adenosine triphosphate (ATP) and pyrophosphate (PPi) as templates. A chiral seed comprising [ANSG‐ATP]S effectively amplifies the overall supramolecular asymmetry when exposed to a mixture of achiral templates (PPi) and monomers (ANSG), owing to its efficient seeding characteristics under kinetic conditions. As a result of efficient co‐operativity, conversely, employing an achiral seed [ANSG‐PPi]S in a mixture of chiral templates (ATP) and monomers (ANSG) results in the attenuation of asymmetry, highlighting the effective modulation achievable through the seeding approach, an unprecedented observation in the field. Exploiting the efficient aggregation‐induced emission enhancement (AIEE) of the resultant supramolecular polymers further extends the amplification and attenuation of circularly polarized luminescence (CPL) as a potential function. [ABSTRACT FROM AUTHOR]

The synthesis of [2]rotaxanes stoppered with one or two dipyrromethane groups has opened a route for the construction of mechanically interlocked molecules incorporating various porphyrinoid stations. The exploitation of those precursors allowed the creation of [3]rotaxanes and [2]catenanes based on the calix[4]phyrin motif, presenting intriguing molecular dynamics. The intrinsic flexibility of the porphyrinoid allowed the introduction of a new type of molecular motion within the rotaxanes, termed fluttering. The latter involved a bending of the axle, interconverting two angular‐shaped stereoisomers of the rotaxane through a planarised transition state. Simple chemical transformations, i.e. methylation and (de)protonation of the [3]rotaxane and [2]catenane allowed controllable transformations within the conformationally flexible calix[4]phyrin‐incorporated mechanically interlocked porphyrinoids. [ABSTRACT FROM AUTHOR]

Receptors for carboxylate anions have many possible biomedical applications, including mimicry of the vancomycin group of antibiotics. However, binding carboxylates in water, the biological solvent, is highly challenging due to the hydrophilicity of these polar anions. Here we report, for the first time, the recognition of simple carboxylates such as acetate and formate in water by synthetic receptors with charge‐neutral binding sites. The receptors are solubilised by polyanionic side‐chains which, remarkably, do not preclude anion binding. The tricyclic structures feature two identical binding sites linked by polyaromatic bridges, capable of folding into closed, twisted conformations. This folding is hypothesised to preorganise the structures for anion recognition, mimicking the process which generates many protein binding sites. The architecture is suitable for elaboration into enclosed structures with potential for selective recognition of biologically relevant carboxylates. [ABSTRACT FROM AUTHOR]

[2]Rotaxanes offer unique opportunities for studying and modulating charge separation and energy transfer, because the mechanical bond allows the robust, yet spatially dynamic tethering of photoactive groups. In this work, we synthesized [2]rotaxane triads comprising a central (aza)[10]CPP⊃C60 bis‐adduct complex and two zinc porphyrin stoppers to address how the movable nanohoop affects light‐induced charge separation and energy transfer between the rotaxane subcomponents. We found that neither the parent nanohoop [10]CPP nor its electron‐deficient analogue aza[10]CPP actively participate in charge separation. In contrast, the nanohoops completely prevented through‐space charge separation. This result is likely due to supramolecular "shielding", because charge separation was observed in the thread that acted as reference dyad. On the other hand, the suppression of electron transfer allowed the observation of energy transfer from the porphyrin triplet to the fullerene triplet state with a lifetime of ca. 25 μs. The presence of the interlocked nanohoops therefore leads to a dramatic switch between charge separation and energy transfer. We suggest that our results explain observations made by others in photovoltaic devices comprising nanohoops and may pave the way toward strategic uses of mechanically interlocked architectures in devices that feature (triplet) energy transfer. [ABSTRACT FROM AUTHOR]

Promoting the generation of triplet states is essential for developing efficient photocatalytic systems. This research presents a novel approach of host‐stabilized through‐space conjugation via the combination of covalent and non‐covalent methods. The designed building block, 4,4′‐(1,4(1,4)‐dibenzene cyclohexaphane‐1,4‐diyl)bis(1‐phenylpyridinium) chloride, features inherently stable through‐space conjugation. When this block forms a 1 : 1 host–guest complex with cucurbit[8]uril, the through‐space conjugation is further stabilized within the confined cavity. Both the generation and lifetime of triplet state are significantly increased, resulting from the host‐stabilized through‐space conjugation. Additionally, the ultrahigh binding constant of 6.58×1014 M−1 ensures the persistence of host‐stabilization effect. As a result, the host–guest complex acts as a highly efficient catalyst in the photocatalytic oxidation of thioether and aromatic alcohol. In the photodegradation of lignin, a complex natural product, the host–guest complex also exhibits high efficiency, demonstrating its robustness. This line of research is anticipated to enrich the toolbox of supramolecular photochemistry and provide a strategy for fabricating efficient supramolecular photocatalysts. [ABSTRACT FROM AUTHOR]

Modulating charge transfer (CT) interactions between donor and acceptor molecules may give rise to unique dynamic changes in physicochemical properties, exhibiting great importance in supramolecular chemistry and materials science. In this work, we demonstrate the first instance of reversible photomodulation of donor‐acceptor (D−A) CT interaction in the solid state. Pyridinium‐based chromophore featuring π‐conjugated D−A structures can not only function as a good electron acceptor to undergo photoinduced electron transfer (ET) or engage in intermolecular CT interaction, but also exhibit unique dual emission depending on the excitation wavelengths. The rotatable C−C single bonds within D−A pairs enhance the tunability of molecular structure. Through the synergy of a photoinduced ET and an excited‐state conformational change, the intermolecular CT interaction can be switched on and off by alternate light irradiation to enable reversibly modulation of the affinity between donor and acceptor molecules, accompanied by visual color switching and fluorescence on‐off as feedback signals. [ABSTRACT FROM AUTHOR]

Polysarcosine emerges as a promising alternative to polyethylene glycol (PEG) in biomedical applications, boasting advantages in biocompatibility and degradability. While the self-assembly behavior of block copolymers containing polysarcosine-containing polymers has been reported, their potential for shape transformation remains largely untapped, limiting their versatility across various applications. In this study, we present a comprehensive methodology for synthesizing, self-assembling, and transforming polysarcosine-poly(benzyl glutamate) block copolymers, resulting in the formation of bowl-shaped vesicles, disks, and stomatocytes. Under ambient conditions, the shape transformation is restricted to bowl-shaped vesicles due to the membrane's flexibility and permeability. However, dehydration of the polysarcosine broadens the possibilities for shape transformation. These novel structures exhibit asymmetry and possess the capability to encapsulate smaller structures, thereby broadening their potential applications in drug delivery and nanotechnology. Our findings shed light on the unique capabilities of polysarcosine-based polymers, paving the way for further exploration and harnessing of their distinctive properties in biomedical research.

Mastering the manipulation of the electron spin plays a crucial role in comprehending the behavior of organic materials in several applications, such as asymmetric catalysis, chiroptical switches, and electronic devices. A promising avenue for achieving such precise control lies in the Chiral Induced Spin Selectivity (CISS) effect, where electrons with a favored spin exhibit preferential transport through chiral assemblies of specific handedness. Chiral supramolecular polymers emerge as excellent candidates for exploring the CISS effect due to their ability to modulate their helical structure through noncovalent interactions. In this context, systems capable of responding to external stimuli are particularly intriguing, sometimes even displaying chirality inversion. This study unveils spin selectivity in chiral supramolecular polymers, derived from single enantiomers, through scanning tunneling microscopy conducted in scanning tunneling spectroscopy mode. Following two distinct sample preparation protocols for each enantiomer, we generate supramolecular polymers with opposite handedness and specific spin transport characteristics. Our primary focus centers on chiral π-conjugated building blocks, with the aim of advancing novel systems that can inspire the organic spintronics community from a supramolecular chemistry level. [ABSTRACT FROM AUTHOR]