Polymer-Fullerene Network Formation via Light-Induced Crosslinking.

A facile and efficient methodology for the formation of polymer-fullerene networks via a light-induced reaction is reported. The photochemical crosslinking is based on a nitrile imine-mediated tetrazole-ene cycloaddition reaction, which proceeds catalyst-free under UV-light irradiation (λmax = 320 nm) at ambient temperature. A tetrazole-functionalized polymer (Mn = 6500 g mol(-1) , Ð = 1.3) and fullerene C60 are employed for the formation of the hybrid networks. The tetrazole-functionalized polymer as well as the fullerene-containing networks are carefully characterized by NMR spectrometry, size exclusion chromatography, infrared spectroscopy, and elemental analysis. Furthermore, thermal analysis of the fullerene networks and their precursors is carried out. The current contribution thus induces an efficient platform technology for fullerene-based network formation.

[1]  S. Yao,et al.  Tetrazole Photoclick Chemistry: Reinvestigating Its Suitability as a Bioorthogonal Reaction and Potential Applications. , 2016, Angewandte Chemie.

[2]  M. Wegener,et al.  Wavelength selective polymer network formation of end-functional star polymers. , 2016, Chemical communications.

[3]  Yusuf Yagci,et al.  Fullerene-Attached Polymeric Homogeneous/Heterogeneous Photoactivators for Visible-Light-Induced CuAAC Click Reactions , 2016 .

[4]  C. Barner‐Kowollik,et al.  Fluorescent Covalently Cross-Linked Cellulose Networks via Light-Induced Ligation. , 2016, ACS macro letters.

[5]  M. Wegener,et al.  Designing π-conjugated polymeric nano- and microstructures via light induced chemistry , 2015 .

[6]  T. N. Ahipa,et al.  Polymer design for solar cell – Current trend and future scenario , 2015 .

[7]  I. McCulloch,et al.  Organic photovoltaics: Crosslinking for optimal morphology and stability , 2015 .

[8]  C. Barner‐Kowollik,et al.  Light-driven nitrile imine-mediated tetrazole-ene cycloaddition as a versatile platform for fullerene conjugation. , 2015, Chemical communications.

[9]  M. Wegener,et al.  Rapid Thiol‐Yne‐Mediated Fabrication and Dual Postfunctionalization of Micro‐Resolved 3D Mesostructures , 2015 .

[10]  X. Jing,et al.  Light-induced synthesis of cross-linked polymers and their application in explosive detection , 2015 .

[11]  A. Facchetti,et al.  Thermal Stabilisation of Polymer–Fullerene Bulk Heterojunction Morphology for Efficient Photovoltaic Solar Cells , 2014, Advanced materials.

[12]  Jens Ludwig,et al.  π-conjugated polymer-fullerene covalent hybrids via ambient conditions Diels-Alder ligation. , 2014, Small.

[13]  C. Barner‐Kowollik,et al.  Photochemical Design of Functional Fluorescent Single-Chain Nanoparticles. , 2014, ACS macro letters.

[14]  J. Fischer,et al.  Fabrication and Spatially Resolved Functionalization of 3D Microstructures via Multiphoton‐Induced Diels–Alder Chemistry , 2014 .

[15]  Chain‐Shu Hsu,et al.  Applications of functional fullerene materials in polymer solar cells , 2014 .

[16]  Guillermo C Bazan,et al.  Design and synthesis of molecular donors for solution-processed high-efficiency organic solar cells. , 2014, Accounts of chemical research.

[17]  Qing Lin,et al.  Design of oligothiophene-based tetrazoles for laser-triggered photoclick chemistry in living cells. , 2013, Chemical communications.

[18]  C. Barner‐Kowollik,et al.  Photo-induced ligation of acrylonitrile-butadiene rubber: Selective tetrazole-ene coupling of chain-end-functionalized copolymers of 1,3-butadiene , 2013 .

[19]  Ru Cheng,et al.  In situ forming hydrogels via catalyst-free and bioorthogonal "tetrazole-alkene" photo-click chemistry. , 2013, Biomacromolecules.

[20]  Benjamin Richter,et al.  Preparation of reactive three-dimensional microstructures via direct laser writing and thiol-ene chemistry. , 2013, Macromolecular rapid communications.

[21]  Y. Yagcı,et al.  Visible Light-Induced Cationic Polymerization Using Fullerenes. , 2012, ACS macro letters.

[22]  Andrew I. Cooper,et al.  Nanoporous organic polymer networks , 2012 .

[23]  A. Jen,et al.  Functional fullerenes for organic photovoltaics , 2012 .

[24]  Xia Ding,et al.  A Multiresponsive, Shape‐Persistent, and Elastic Supramolecular Polymer Network Gel Constructed by Orthogonal Self‐Assembly , 2012, Advanced materials.

[25]  Hee-Young Park,et al.  Mechanophotopatterning on a Photoresponsive Elastomer , 2011, Advanced materials.

[26]  Jianjun Li,et al.  Synthesis of oligofluorene modified C60 derivatives for organic solar cell applications , 2011 .

[27]  Yongfang Li,et al.  Fullerene derivative acceptors for high performance polymer solar cells. , 2011, Physical chemistry chemical physics : PCCP.

[28]  Francesco Giacalone,et al.  New Concepts and Applications in the Macromolecular Chemistry of Fullerenes , 2010, Advanced materials.

[29]  Shangfeng Yang,et al.  Donor-π-acceptor double-cable polythiophenes bearing fullerene pendant with tunable donor/acceptor ratio: A facile postpolymerization , 2010 .

[30]  C. Frisbie,et al.  Synthesis, Optical Properties, and Microstructure of a Fullerene-Terminated Poly(3-hexylthiophene) , 2009 .

[31]  T. Emrick,et al.  Synthesis and photophysical property of well-defined donor–acceptor diblock copolymer based on regioregular poly(3-hexylthiophene) and fullerene , 2009 .

[32]  Yuehua Wu,et al.  Fabrication of dendrimer-like fullerene (C60)-decorated oligomeric intumescent flame retardant for reducing the thermal oxidation and flammability of polypropylene nanocomposites , 2009 .

[33]  T. Yamauchi,et al.  A Simple Preparation of C60-Poly(ethylene glycol) Gel and its Properties , 2009 .

[34]  N. Clark,et al.  Formation and Surface Modification of Nanopatterned Thiol‐ene Substrates using Step and Flash Imprint Lithography , 2008 .

[35]  Wenjiao Song,et al.  Selective functionalization of a genetically encoded alkene-containing protein via "photoclick chemistry" in bacterial cells. , 2008, Journal of the American Chemical Society.

[36]  Michael M. Madden,et al.  A photoinducible 1,3-dipolar cycloaddition reaction for rapid, selective modification of tetrazole-containing proteins. , 2008, Angewandte Chemie.

[37]  Y. Inoue,et al.  Synthesis and characterization of fullerene grafted poly(ε-caprolactone) , 2008 .

[38]  Sheng Dai,et al.  Fullerene containing polymers: a review on their synthesis and supramolecular behavior in solution. , 2007, Journal of nanoscience and nanotechnology.

[39]  Neil L. Campbell,et al.  Hydrogen Storage in Microporous Hypercrosslinked Organic Polymer Networks , 2007 .

[40]  F. Giacalone,et al.  Fullerene polymers: synthesis and properties. , 2006, Chemical reviews.

[41]  A. Mouithys-Mickalad,et al.  New nanostructured materials based on fullerene and biodegradable polyesters , 2006 .

[42]  Donal D. C. Bradley,et al.  A strong regioregularity effect in self-organizing conjugated polymer films and high-efficiency polythiophene:fullerene solar cells , 2006 .

[43]  L. Wang,et al.  Novel C60‐Anchored Two‐Armed Poly(tert‐butyl acrylate): Synthesis and Characterization , 2005 .

[44]  B. Tang,et al.  Linear or branched structure? Probing molecular architectures of fullerene–styrene copolymers by size exclusion chromatographs with online right-angle laser-light scattering and differential viscometric detectors , 2004 .

[45]  N. Peppas,et al.  Structure and Interactions in Covalently and Ionically Crosslinked Chitosan Hydrogels for Biomedical Applications , 2003 .

[46]  Qiying Chen,et al.  [60]Fullerene-containing polyurethane films with large ultrafast nonresonant third-order nonlinearity at telecommunication wavelengths. , 2003, Journal of the American Chemical Society.

[47]  G. Tomaschewski,et al.  Synthesis, photomodification and characterization of homo- and copolymers with 2,5-bisaryltetrazolyl pendant groups , 1997 .

[48]  C. Kuo,et al.  Polyhydroxylated C60 Cross-Linked Polyurethanes , 1995 .

[49]  O. Ivashkevich,et al.  The thermal decomposition of tetrazoles , 1992 .

[50]  Paul Brumer,et al.  Control of unimolecular reactions using coherent light , 1986 .

[51]  R. Huisgen,et al.  1.3‐Dipolare Cycloadditionen, XXV. Der Nachweis des freien Diphenylnitrilimins als Zwischenstufe bei Cycloadditionen , 1967 .

[52]  R. Huisgen,et al.  Communications: The Formation of Nitrile Imines in the Thermal Breakdown of 2,5-Disubstituted Tetrazoles , 1959 .