Post-synthetic π-extension of perylene conjugated porous polymer via APEX reactions: tunable optical and gas storage properties.

Double post-synthetic modification is used for the π-extension of perylene based conjugated porous polymers (CPPs) using sequential annulative π-extension (APEX) reactions. This approach enabled us to synthesize new CPPs rendered with donor-acceptor rigid π-systems such as benzoperylene anhydride (BPA-CPP) and benzoperylene benzimidazole (BPBI-CPP) with distinct optical properties. Despite its low surface area, BPBI-CPP shows good CO2 uptake and pH responsive behaviour owing to the presence of benzimidazole rings.

[1]  Yogesh Kumar Maurya,et al.  Recent Advances in Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds , 2021, Chemical reviews.

[2]  T. Maji,et al.  Metal-Free Catalysis: A Redox-Active Donor-Acceptor Conjugated Microporous Polymer for Selective Visible-Light-Driven CO2 Reduction to CH4. , 2021, Journal of the American Chemical Society.

[3]  M. Barawi,et al.  Conjugated Porous Polymers: Ground‐Breaking Materials for Solar Energy Conversion , 2021, Advanced Energy Materials.

[4]  Rahul Sahu,et al.  Supramolecular Depolymerization in the Mixture of Two Poor Solvents: Mechanistic Insights and Modulation of Supramolecular Polymerization of Ionic π-Systems. , 2020, Angewandte Chemie.

[5]  M. Krompiec,et al.  Diels–Alder Cycloaddition to the Bay Region of Perylene and Its Derivatives as an Attractive Strategy for PAH Core Expansion: Theoretical and Practical Aspects , 2020, Molecules.

[6]  P. Zaikin,et al.  The Diels-Alder Reaction for the Synthesis of Polycyclic Aromatic Compounds , 2019, European Journal of Organic Chemistry.

[7]  Wei Liu,et al.  A New Conjugated Porous Polymer with Covalently Linked Polysulfide as Cathode Material for High-Rate Capacity and High Coulombic Efficiency Lithium–Sulfur Batteries , 2019, The Journal of Physical Chemistry C.

[8]  Reiner Sebastian Sprick,et al.  Photocatalytic Hydrogen Evolution from Water Using Fluorene and Dibenzothiophene Sulfone-Conjugated Microporous and Linear Polymers , 2018, Chemistry of Materials.

[9]  Tobias A. F. König,et al.  Fluorescent Sulphur- and Nitrogen-Containing Porous Polymers with Tuneable Donor-Acceptor Domains for Light-Driven Hydrogen Evolution. , 2018, Chemistry.

[10]  Chenghui Zhang,et al.  Post-cationic Modification of a Pyrimidine-Based Conjugated Microporous Polymer for Enhancing the Removal Performance of Anionic Dyes in Water. , 2018, Chemistry.

[11]  K. Itami,et al.  Annulative π-Extension (APEX): Rapid Access to Fused Arenes, Heteroarenes, and Nanographenes. , 2017, Angewandte Chemie.

[12]  Yuan Yuan,et al.  N,N′-Bicarbazole: A Versatile Building Block toward the Construction of Conjugated Porous Polymers for CO2 Capture and Dyes Adsorption , 2017 .

[13]  P. Jena,et al.  Enhanced Carbon Dioxide Capture from Landfill Gas Using Bifunctionalized Benzimidazole-Linked Polymers. , 2016, ACS applied materials & interfaces.

[14]  J. P. Olivier,et al.  Physisorption of gases, with special reference to the evaluation of surface area and pore size distribution (IUPAC Technical Report) , 2015 .

[15]  Xiaodong Zhuang,et al.  Conjugated Microporous Polymers with Dimensionality‐Controlled Heterostructures for Green Energy Devices , 2015, Advanced materials.

[16]  Reiner Sebastian Sprick,et al.  Tunable organic photocatalysts for visible-light-driven hydrogen evolution. , 2015, Journal of the American Chemical Society.

[17]  H. Sakaguchi,et al.  Width‐Controlled Sub‐Nanometer Graphene Nanoribbon Films Synthesized by Radical‐Polymerized Chemical Vapor Deposition , 2014, Advanced materials.

[18]  T. Maji,et al.  Porous polyimides from polycyclic aromatic linkers: Selective CO2 capture and hydrogen storage , 2014 .

[19]  A. Cooper,et al.  Post-synthetic modification of conjugated microporous polymers , 2014 .

[20]  J. J. Schneider,et al.  Gas adsorption studies of CO2 and N2 in spatially aligned double-walled carbon nanotube arrays , 2013 .

[21]  M. Antonietti,et al.  Surface area control and photocatalytic activity of conjugated microporous poly(benzothiadiazole) networks. , 2013, Angewandte Chemie.

[22]  Subi J. George,et al.  Guest-responsive reversible swelling and enhanced fluorescence in a super-absorbent, dynamic microporous polymer. , 2012, Chemistry.

[23]  T. Maji,et al.  Perylene Based Porous Polyimides: Tunable, High Surface Area with Tetrahedral and Pyramidal Monomers , 2012 .

[24]  B. Kiskan,et al.  Versatile Postmodification of Conjugated Microporous Polymers Using Thiol-yne Chemistry. , 2012, ACS macro letters.

[25]  Tapas Kumar Maji,et al.  Extended phenylene based microporous organic polymers with selective carbon dioxide adsorption , 2011 .

[26]  D. Jiang,et al.  Light-harvesting conjugated microporous polymers: rapid and highly efficient flow of light energy with a porous polyphenylene framework as antenna. , 2010, Journal of the American Chemical Society.

[27]  Wenchuan Wang,et al.  Targeted synthesis of a porous aromatic framework with high stability and exceptionally high surface area. , 2009, Angewandte Chemie.