Electrochemical Polymerization Induced Chirality Fixation of Crystalline Pillararene-Based Polymer and Its Application in Interfacial Chiral Sensing.

A new strategy has been developed for the direct chirality fixation, which is induced by electrochemical polymerization, of macrocyclic hosts pillar[5]arene. Taking advantage of electrochemical polymerization, thiophene-modified pillar[5]arene monomers (Th-P[5]A) have been regularly arranged under the action of an electric field to form chiral nanofiber-like crystalline pillar[5]arene-based polymers (poly-Th-P[5]A), showing a significant circular dichroism (CD) signal. With the active photochemical properties, poly-Th-P[5]A is first used as a photoelectrochemical (PEC) chiral sensor for the identification and determination of l- and d-ascorbic acid (l-AA, d-AA) without adding any extra photoactive probes. Importantly, the chiral recognition between poly-Th-P[5]A and l-AA also triggers a polarity conversion for the photocurrent of the polymer, and it greatly results in a broad chiral detection range for l-AA, crossing 6 orders of magnitude. This work provides a promotional strategy for building a PEC chiral recognition platform based on pillararenes.

[1]  Hong Jiang,et al.  Highly Stable Zr(IV)-Based Metal-Organic Frameworks for Chiral Separation in Reversed-Phase Liquid Chromatography. , 2020, Journal of the American Chemical Society.

[2]  Feihe Huang,et al.  Acid/Base-Tunable Unimolecular Chirality Switching of a Pillar[5]azacrown Pseudo[1]Catenane. , 2020, Journal of the American Chemical Society.

[3]  Cheng Lu,et al.  N and Sn Co-Doped hematite photoanodes for efficient solar water oxidation. , 2020, Journal of colloid and interface science.

[4]  X. Qu,et al.  Neutrophil-Membrane-Directed Bioorthogonal Synthesis of Inflammation-Targeting Chiral Drugs , 2020, Chem.

[5]  Zhonghai Zhang,et al.  Ionic Current Rectification Triggered Photoelectrochemical Chiral Sensing Platform for Recognition of Amino Acid Enantiomers on Self-Standing Nanochannel Arrays. , 2020, Analytical chemistry.

[6]  Dan Su,et al.  Redox-Triggered Chirality Switching and Guest-Capture/Release with a Pillar[6]arene-Based Molecular Universal Joint. , 2020, Angewandte Chemie.

[7]  T. Darmanin,et al.  Tuning nanotubular structures by templateless electropolymerization with thieno[3,4-b]thiophene-based monomers with different substituents and water content. , 2019, Journal of colloid and interface science.

[8]  Xiyun Yan,et al.  Advances in chiral nanozymes: a review , 2019, Microchimica Acta.

[9]  Wenjing Song,et al.  Novel Electrochemical Pretreatment for Preferential Removal of Nonylphenol in Industrial Wastewater: Biodegradability Improvement and Toxicity Reduction. , 2019, Environmental science & technology.

[10]  Feihe Huang,et al.  Supramolecular‐Macrocycle‐Based Crystalline Organic Materials , 2019, Advanced materials.

[11]  B. Tang,et al.  AEE Conjugated Polymeric Supramolecular Network: an Efficient Light-Harvesting System with Ultrahigh Antenna Effect. , 2019, Angewandte Chemie.

[12]  Demei Tian,et al.  Enantioselective Dynamic Self-Assembly of Histidine Droplets on Pillar[5]arene-Modified Interfaces. , 2019, ACS applied materials & interfaces.

[13]  Liguang Xu,et al.  Chirality‐Based Biosensors , 2018, Advanced Functional Materials.

[14]  Y. Hsu,et al.  Novel p-n heterojunction copper phosphide/cuprous oxide photocathode for solar hydrogen production. , 2018, Journal of colloid and interface science.

[15]  Lei Ge,et al.  Truly Immobilization-Free Diffusivity-Mediated Photoelectrochemical Biosensing Strategy for Facile and Highly Sensitive MicroRNA Assay. , 2018, Analytical chemistry.

[16]  Jie Huang,et al.  Mesoporous tungsten oxide modified by nanolayered manganese-calcium oxide as robust photoanode for solar water splitting. , 2018, Journal of colloid and interface science.

[17]  A. Facchetti,et al.  On the Molecular Origin of Charge Separation at the Donor–Acceptor Interface , 2018 .

[18]  A. Calcaterra,et al.  The market of chiral drugs: Chiral switches versus de novo enantiomerically pure compounds , 2018, Journal of pharmaceutical and biomedical analysis.

[19]  Linxian Xu,et al.  Pillar[5]arene-Diketopyrrolopyrrole Fluorescent Copolymer: A Promising Recognition and Adsorption Material for Adiponitrile by Selective Formation of a Conjugated Polypseudorotaxane. , 2017, Macromolecular rapid communications.

[20]  D. Armstrong,et al.  Ultrafast Chiral Chromatography as the Second Dimension in Two-Dimensional Liquid Chromatography Experiments. , 2017, Analytical chemistry.

[21]  Peter A Willis,et al.  Enhanced Resolution of Chiral Amino Acids with Capillary Electrophoresis for Biosignature Detection in Extraterrestrial Samples. , 2016, Analytical chemistry.

[22]  Lei Jiang,et al.  Dynamic Self-Assembly Adhesion of a Paraquat Droplet on a Pillar[5]arene Surface. , 2016, Angewandte Chemie.

[23]  Wenqiang Lai,et al.  Target-induced nano-enzyme reactor mediated hole-trapping for high-throughput immunoassay based on a split-type photoelectrochemical detection strategy. , 2015, Analytical chemistry.

[24]  David Beljonne,et al.  A dynamic supramolecular polymer with stimuli-responsive handedness for in situ probing of enzymatic ATP hydrolysis , 2014, Nature Communications.

[25]  Wei-Wei Zhao,et al.  Photoelectrochemical DNA biosensors. , 2014, Chemical reviews.

[26]  T. Ogoshi,et al.  Solvent- and achiral-guest-triggered chiral inversion in a planar chiral pseudo[1]catenane. , 2013, Angewandte Chemie.

[27]  H. Goto,et al.  Horizontal and Vertical Orientation of Polythiophenes by Electrochemical Polymerization in Magnetically Aligned Smectic Liquid Crystal. , 2013, ACS macro letters.

[28]  S. Sampath,et al.  In Situ Electrochemical Polymerization at Air−Water Interface: Surface-Pressure-Induced, Graphene-Oxide-Assisted Preferential Orientation of Polyaniline , 2012 .

[29]  S. Kawauchi,et al.  High-yield diastereoselective synthesis of planar chiral [2]- and [3]rotaxanes constructed from per-ethylated pillar[5]arene and pyridinium derivatives. , 2012, Chemistry.

[30]  Yingzi Fu,et al.  A new strategy for chiral recognition of amino acids. , 2012, Chemical communications.

[31]  T. Ward,et al.  Chiral separations: a review of current topics and trends. , 2012, Analytical chemistry.

[32]  T. Ogoshi,et al.  Planar-chiral macrocyclic host pillar[5]arene: no rotation of units and isolation of enantiomers by introducing bulky substituents. , 2011, Organic letters.

[33]  S. Fujinami,et al.  Facile, rapid, and high-yield synthesis of pillar[5]arene from commercially available reagents and its X-ray crystal structure. , 2011, The Journal of organic chemistry.

[34]  Yoshiaki Nakamoto,et al.  para-Bridged symmetrical pillar[5]arenes: their Lewis acid catalyzed synthesis and host-guest property. , 2008, Journal of the American Chemical Society.

[35]  Hiroshi Sakaguchi,et al.  Electrochemical epitaxial polymerization of single-molecular wires , 2004, Nature materials.