Macromolecular engineering in functional polymers via 'click chemistry' using triazolinedione derivatives. (February 2021)

• Record Type: Journal Article
• Authors: Mondal, Prantik; Behera, Prasanta K.; Singha, Nikhil K.
• Is Part Of: Progress in polymer science. Volume 113(2021)
• Publication Date: 2021-02
• Subjects: Triazolinediones -- 'Click chemistry' -- Functional polymers -- Ultrafast reaction -- Alder-ene (AE) -- Diels-Alder (DA) -- Electrophilic substitution (ES); 9-AM 9-anthracenemethanol -- AAP Photoresponsive Azopyrazoles -- ABC Isopropyl-Ethyl-Cyclohexyl -- ABS Acrylonitrile–Butadiene–Styrene -- ACN Acetonitrile -- ADMET Acyclic Diene Metathesis -- AE Alder-ene -- AlF 1H, 1H, 2H, 2H-perfluorodecyl iodide (Alkyl) -- AlFTAD Perfluoroalkyl-1, 2, 4-triazoline-3, 5-dione -- AlFSC 4-perfluorophenyl semicarbazide -- AlFUr 4-perfluorophenyl urazole -- APC Aliphatic polycarbonates -- ArF 4-perfluorophenyl amine (Aromatic) -- ArFTAD Perfluoroaryl -1, 2, 4-triazoline-3, 5-dione -- Arg Arginine -- ATRP Atom Transfer Radical Polymerization -- BCP Block Copolymer -- BLYP Becke, Lee-Yang-Parr -- B3LYP Becke, 3-parameter, Lee-Yang-Parr -- bis-TAD 4, 4′-(1, 4-Phenylene)-bis(1, 2, 4-triazoline-3, 5-dione) -- BSA Bovine serum albumin -- BuTAD n-Butyl-1, 2, 4-triazoline-3, 5-dione -- CC Cyclic Carbonate -- CI Configuration Interaction -- CLD Crosslink Density -- cm centimeter -- CNCs Cellulose Nanocrystals -- COOH-Hex-TAD 1-carboxyhexyl-1, 2, 4-triazoline-3, 5-dione -- COOH-PhTAD 4-(4-carboxyphenyl)- 1, 2, 4-triazoline-3, 5-dione -- COOEt-PhTAD 4-(4-ethylbenzoate)-1, 2, 4-triazoline-3, 5-dione -- Cp Cyclopentadiene -- CTA Chain Transfer Agent -- CuAAC Copper (I) Catalyzed Alkyne-Azide -- DA Diels-Alder -- DABCO-Br Brominated 1, 4-diazabicyclo [2.2.2]octane -- DCM Dichloromethane -- DEAD Diethyl Azodicarboxylate -- DFT Density Functional Theory -- dh Hydrodynamic radius -- DMF Dimethyl-formamide -- DMSO Dimethyl sulfoxide -- DSC Differential Scanning Calorimetry -- DX Doubly Crosslinked Hydrogels -- EC Ethyl Carbazate -- EGDMA Ethylene Glycol Dimethacrylate -- ES Electrophilic Substitution -- EUG Eucommia Ulmoides Gum -- FCI Full Configuration Interaction -- FE-SEM Field Emission-Scanning Electron Microscopy -- Fmoc Fluorenylmethyloxycarbonyl -- FTAD 4-(m-(Trifluoromethyl)phenyl)-l, 2, 4-triazoline-3, 5-dione -- G' Storage modulus -- G" Loss modulus -- GC Glassy Carbon -- GC-TAD Glassy carbon -1, 2, 4-triazoline-3, 5-dione -- Glu Glutamic acid -- GMA Glycidyl Methacrylate -- g mol-1 gram per mole -- h hour -- H-bond Hydrogen bonding -- HDA Hetero-Diels-Alder -- HDI- TAD Hexamethylene diisocyanate 1, 2, 4-triazoline-3, 5-dione -- HDEO trans-2, 4-hexadiene-1-ol -- HE Healing efficiency -- HEA Hydroxyethyl acrylate -- Hex-TAD Hexyl-1, 2, 4-triazoline-3, 5-dione -- HF Hartree-Fock -- His Histidine -- H-PhTAD 4-phenyl-1, 2, 4-triazoline-3, 5-dione -- IPDI- TAD Isophorone diisocyanate 1, 2, 4-triazoline-3, 5-dione -- iPP Isotactic polypropylene -- IZ zwitterionic intermediate -- K2CO3 Potassium carbonate -- kcal kilocalorie -- kDa kilodalton -- LC Liquid chromatography -- LEDs Light Emitting Diodes -- LSDMs Light Stabilized Dynamic Materials -- lys Lysine -- MDI- TAD Methylene diphenyl diisocyanate 1, 2, 4-triazoline-3, 5-dione -- Mn Number average molecular weight -- MO Molecular Orbital -- MP Møller-Plesset -- MPa Megapascal -- mW milliwatt -- N2O4 Dinitrogen tetroxide -- nBA n-butyl acrylate -- NC Nanocomposite -- NCA n-carboxyanhydride -- nm nanometer -- NO2-PhTAD 4-(4-nitrophenyl)-1, 2, 4-triazoline-3, 5-dione -- NPs Nanoparticles -- Octenyl-SAM Octenyltrichlorosilane self-assembled monolayers -- P3CR Passerini three-component reaction -- PA Polyacetylene -- PAAPA Poly (photoresponsive azopyrazole acrylate) -- PB Polybutadiene -- PBS Phosphate-buffered saline -- PCDA Poly (β-cyclodextrin acrylate) -- PCL Polycaprolactone -- PDI Polydispersity index -- pDMA protein-Poly(N, N-dimethylacrylamide) -- PEG Polyethylene glycol -- PEGMA Poly(ethylene glycol)methyl ether methacrylate -- PEO Poly(ethylene glycol) monomethylether -- PHEA Poly (hydroxyethyl acrylate) -- PiBA Poly (isobornyl acrylate) -- PMAs Polymethacylates -- PMA-TAD Polymethacrylate-1, 2, 4-triazoline-3, 5-dione -- PMMA Poly (methyl methacrylate) -- PNB Polynorbornene -- PnBA Poly (n-butyl acrylate) -- PnBA-TAD Poly (n-butyl acrylate)-1, 2, 4-triazoline-3, 5-dione -- PNIPAM-Ur Poly(N-isopropylacrylamide) urazole -- poly(LSL)s Poly (lactonic sophorolipid) -- PONPs Plant oil nanoparticles -- POSS-TAD Isobutyl polyhedral oligomeric silsesquioxane- 1, 2, 4-triazoline-3, 5-dione -- POSS-NH2 Aminopropylisobutyl polyhedral oligomeric silsesquioxane -- POSS-SC Semicarbazide propylisobutyl polyhedral oligomeric silsesquioxane -- POSS-Ur Urazole propylisobutyl polyhedral oligomeric silsesquioxane -- PPEs Poly(phospoester)s -- Prop-TAD Propyl-1, 2, 4-triazoline-3, 5-dione -- PS Polystyrene -- PSBAM Poly (soyabean amide methacrylate) -- PS-b-P4VP Polystyrene-block-poly (4-vinylpyridine) -- PSHD Polyheptadiyne -- PtBA Poly (tert-butyl acrylate) -- PU Polyurethane -- RAFT Reversible addition-fragmentation chain transfer -- ROMP Ring-opening metathesis polymerization -- ROP Ring-opening polymerization -- r.t. Room temperature -- SAM Self-assembled monolayers -- SBAM Soyabean amide methacrylate -- SC Semicarbazides -- SBR Styrene–butadiene Rubber -- SEC Size exclusion chromatography -- Ser Serine -- SHPs Self-healing Polymers -- SI-ATRP Surface initiated-ATRP -- SIS Polystyrene–b-polyisoprene–b-polystyrene -- SM Shape memory -- SMPs Shape Memory Polymers -- SMASH Shape memory assisted self-healing -- SMNC Shape Memory nanocomposite -- SPAAC Strain Promoted Alkyne-Azide Cycloaddition -- SSBR Solution polymerized styrene butadiene rubber -- TAD 1, 2, 4-triazoline-3, 5-dione -- TBD 1, 5, 7-triazabicyclo [4, 4, 0] dec-5-ene -- Tg Glass transition temperature -- THF Tetrahydrofuran -- TPE Thermoplastic elastomer -- Trp Tryptophan -- Tyr Tyrosine -- TS Transition state -- Ur-CTA Urazole-chain transfer agent -- Ur-PnBA Poly (butyl acrylate) with urazole terminal -- Ur-TTC Urazole-functionalized trithiocarbonate -- WCA Water contact angle -- 4-VP 4-Vinyl pyridine -- VB Valence Bond -- β-CD β -cyclodextrin -- Ð Dispersity -- ΔG Change in free energy -- ΔG‡ Free energy barrier; Polymers -- Periodicals; Polymerization -- Periodicals; Polymers -- Industrial applications -- Periodicals; Polymères -- Périodiques; Polymérisation -- Périodiques; 547.7
• DOI: 10.1016/j.progpolymsci.2020.101343
• Languages: English
• ISSNs: 0079-6700

Abstract

Abstract: It has been almost two decades since the concept of 'click' chemistry was anchored in the monumental field of chemistry. Later, numerous chemical approaches have been implemented that exhibit features kindred to 'click' chemistry toolbox. Unlike the synthesis of organic compounds involving typical purification procedures, the modular and orthogonal 'click' concept substantially embraces the material research community with delineating innumerable macromolecular architectures. In polymer chemistry, there are various types of 'click' reactions like copper (I) catalyzed alkyne-azide (CuAAC), strain promoted alkyne-azide cycloaddition (SPAAC), Diels-Alder, Alder-ene, thiol-ene, thio-bromo, etc., are used to prepare different functional polymers. Among the various 'click' reactions, recently, the ultrafast 'click' modification based on different 1, 2, 4-triazoline-3, 5-dione (TAD) derivatives has gained tremendous attention in the broad platform of polymer research. Similar to singlet oxygen, the heterocyclic TAD reagents undergo 'click' conjugation within a concise timescale. Following the uncovering of the conventional routes for synthesizing TADs, few spellbinding categories of research have been carried out to develop different functional polymers for diverse applications. The perspective of this review is to cover the recent fascinating outcomes from TAD based ultrafast 'click' modification of macromolecules. This review highlights the present state-of-the-art of synthesis of new TAD molecules and their use in designing different macromolecular systems with remarkable features based on ultrafast TAD 'click' chemistry. Graphical Abstract: Macromolecular engineering using TAD chemistry, shown via a sketch of a fictional character Mr. Bean, a distinguished comedian, and engineer, with his TAD toolbag. Image, graphical abstract