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Anthracene-Based Thiol–Ene Networks With Thermo-Degradable And Photo-Reversible Properties

J. V. Damme, O. Berg, Joost Brancart, L. Vlaminck, Carolien Huyck, G. Assche, B. V. Mele, F. D. Prez
Published 2017 · Chemistry

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Reversible networks based on an alkene-functionalized dimer of 9-anthracenemethanol were synthesized by photoinitiated radical thiol–ene polyaddition, using either a poly(dimethylsiloxane-co-propylmercaptomethylsiloxane) or a novel aliphatic trithiol synthesized from 1,2,4-trivinylcyclohexane in a simple two-step procedure. The obtained networks were analyzed using differential scanning calorimetry, dynamic mechanical analysis, polarization microscopy, X-ray diffraction, and (photo)rheology. The two types of networks showed weak endothermic transitions between 50 and 60 °C, which proved to originate either from melting of a crystalline anthracene-dimer phase (trithiol network) or from a liquid crystalline phase (PDMS network) based on X-ray diffraction and polarization microscopy. Using rheology, both types of networks were shown to cleanly decompose into multifunctional anthracene monomers at temperatures above 180 °C. Irradiation of these anthracene monomers resulted in the formation of networks having ...
This paper references
10.1039/JM9950502063
Polymer-dispersed liquid crystals
D. Coates (1995)
10.1039/c5sc02223a
Vitrimers: permanent organic networks with glass-like fluidity
Wim Denissen (2016)
Process for the production of 1 , 2 , 4 - trivinylcyclohexane . US 2967895 A ,
D. Fritz (1961)
10.1021/MA011940M
Synthesis and Thin Film Characterization of Poly(styrene-block-methyl methacrylate) Containing an Anthracene Dimer Photocleavable Junction Point
J. Goldbach (2002)
Thiol - vinyl and thiol - yne shape memory polymers for medical use
C. Bowman (2009)
10.1039/B9PY00216B
Thiol-ene “click” reactions and recent applications in polymer and materials synthesis
A. B. Lowe (2010)
Polymerized alkoxysilyl derivatives of norbornene and mercaptans as dental materials
V. Rheinberger (1997)
10.1002/POLA.20774
Photocycloaddition‐induced preparation of nanostructured, cyclic polymers using biscinnamated or biscoumarinated oligo(ethylene glycol)s
Y. Nakayama (2005)
10.1002/ADFM.201404553
Vinylogous Urethane Vitrimers
Wim Denissen (2015)
10.1002/CHIN.200232293
Photodimerization of Anthracenes in Fluid Solutions. Part 2. Mechanistic Aspects of the Photocycloaddition and of the Photochemical and Thermal Cleavage
H. Bouas-Laurent (2002)
Radiation curing in polymer science and technology
Jean-Pierre Fouassier (1993)
10.1126/science.1212648
Silica-Like Malleable Materials from Permanent Organic Networks
Damien Montarnal (2011)
10.1038/PJ.2012.18
Photoinduced mendable network polymer from poly(butylene adipate) end-functionalized with cinnamoyl groups
N. Oya (2012)
10.1039/C1JM13709C
Fluorescence sensing of microcracks based on cycloreversion of a dimeric anthracene moiety
Youngkyu Song (2012)
Photocurable thiol - ene copolymer low gas permeability membranes
C. E. Hoyle (2009)
10.1021/CM902506A
Applications of Photocurable PMMS Thiol−Ene Stamps in Soft Lithography
L. Campos (2009)
10.1021/MA402564A
Low Modulus Dry Silicone-Gel Materials by Photoinduced Thiol–Ene Chemistry
O. Berg (2014)
Polymer electrolyte composition to thiol-enebasis
Kejian Chen (1996)
10.1021/la403425d
Facile functionalization of PDMS elastomer surfaces using thiol-ene click chemistry.
J. Zhang (2013)
10.1039/C3PY00184A
A facile approach for the synthesis of cyclic poly(N-isopropylacrylamide) based on an anthracene–thiol click reaction
B. Liu (2013)
Novel photopolymers and use in dental restorative materials
C. Bowman (2007)
10.1002/adma.201304705
Synthesis of a covalent monolayer sheet by photochemical anthracene dimerization at the air/water interface and its mechanical characterization by AFM indentation.
Payam Payamyar (2014)
10.1002/POLA.20366
Thiol–enes: Chemistry of the past with promise for the future
C. Hoyle (2004)
Thiol - ene - based poly ( alkylsiloxane ) materials for lithography
C. J. Hawker (2009)
10.1016/J.TET.2016.05.077
Synthesis and evaluation of 9-substituted anthracenes with potential in reversible polymer systems
Jonas Van Damme (2016)
10.1039/c3cs60046g
Covalent adaptable networks: smart, reconfigurable and responsive network systems.
Christopher J Kloxin (2013)
10.1002/(SICI)1097-0126(199708)43:4<310::AID-PI739>3.0.CO;2-G
Photoresponsive functionalized vinyl cinnamate polymers: Synthesis and characterization
A. H. Ali (1997)
anthracene−thiol click reaction
D. Fritz (1961)
10.1039/c1lc20388f
Beyond PDMS: off-stoichiometry thiol-ene (OSTE) based soft lithography for rapid prototyping of microfluidic devices.
Carl Fredrik Carlborg (2011)
Sealants oil resistant cured polyacrylate thiol-ene applications gaskets in situ
John G. Woods (2009)
10.1021/ol403015s
Dynamic covalent bond based on reversible photo [4 + 4] cycloaddition of anthracene for construction of double-dynamic polymers.
J. Xu (2013)
Photopolymerizable resin systems for dental restorative materials
C. N. Bowman (2009)
10.1002/CHIN.201023209
Thiol—Ene Click Chemistry
C. Hoyle (2010)
10.1016/J.POLYMER.2016.08.106
Design and application of photo-reversible elastomer networks by using the [4πs+4πs] cycloaddition reaction of pendant anthracene groups
Jakob Manhart (2016)



This paper is referenced by
10.1038/s41598-020-77246-0
Combined light- and heat-induced shape memory behavior of anthracene-based epoxy elastomers
Yuzhan Li (2020)
10.1002/marc.202000369
N-Acyl Dibenzazepine Chemistry as Versatile Approach for Photoreversible Thiol-Ene Networks.
Semira Bener (2020)
10.1016/J.PROGPOLYMSCI.2019.05.001
Photo-cross-linking: A powerful and versatile strategy to develop shape-memory polymers
Hui Xie (2019)
10.1002/adma.201901269
Tailoring the Mechanical Properties of 3D Microstructures Using Visible Light Post-Manufacturing.
Marvin Gernhardt (2019)
10.1016/J.TET.2019.01.007
A novel donor-π-acceptor anthracene monomer : towards faster and milder reversible dimerization
J. V. Damme (2019)
10.1016/J.EURPOLYMJ.2018.06.018
Anthracene-based polyurethane networks: Tunable thermal degradation, photochemical cure and stress-relaxation
J. V. Damme (2018)
10.1021/ACSMACROLETT.7B00494
Poly(thioether) vitrimers via transalkylation of trialkylsulfonium salts
B. Hendriks (2017)
10.1002/POLA.29245
Single-Chain Folding Nanoparticles as Carbon Nanotube Catchers
Mesut Bilgi (2018)
10.1021/acs.macromol.7b01117
Wavelength-Selective Sequential Polymer Network Formation Controlled with a Two-Color Responsive Initiation System.
X. Zhang (2017)
10.1016/j.polymer.2020.122762
Self-healing UV-curable polymer network with reversible Diels-Alder bonds for applications in ambient conditions
D. Ehrhardt (2020)
10.1002/adma.201803463
Reversible Surface Patterning by Dynamic Crosslink Gradients: Controlling Buckling in 2D.
Honghao Hou (2018)
10.1080/15685551.2017.1382028
UV induced reversible chain extension of 1-(2-anthryl)-1-phenylethylene functionalized polyisobutylene
Cimen Ozguc Onal (2017)
10.1039/d0cp03165h
Thermal dissociation of anthracene photodimers in the condensed state: kinetic evaluation and complex phase behaviour.
Joost Brancart (2020)
10.1039/d0py01119c
Visible-light reversible photopolymerisation: insights via online photoflow – electrospray ionisation – mass spectrometry
M. Walle (2020)
10.1039/c9sc06235a
Room temperature crystallization of amorphous polysiloxane using photodimerization
Taylor Wright (2020)
10.1039/c9tc05410c
Noncovalent functionalization of hole-transport materials with multi-walled carbon nanotubes for stable inverted perovskite solar cells
L. Yu (2019)
10.1016/J.PROGPOLYMSCI.2018.02.002
Anthracene-containing polymers toward high-end applications
J. V. Damme (2018)
10.1002/anie.201912902
Covalent adaptable networks with tunable exchange rates based on reversible thiol-yne cross-linking.
Niels Van Herck (2019)
10.1016/J.POLYMER.2018.08.026
Room-temperature versus heating-mediated healing of a Diels-Alder crosslinked polymer network
M. Díaz (2018)
10.1002/PPSC.201800030
Anthracene‐Based Colloidal Polymer Nanoparticles: Their Photochemical Ligation and Waterborne Coating Applications
S. Chattopadhyay (2018)
10.1016/J.PORGCOAT.2019.105215
Urethane polythioether self-crosslinking resins
B. Hendriks (2019)
10.1039/d0py00075b
Polymer actuators based on covalent adaptable networks
Yahe Wu (2020)
10.1039/C7RA12201B
Light- and heat-triggered reversible luminescent materials based on polysiloxanes with anthracene groups
Dongdong Han (2017)
10.1007/s10118-018-2107-x
Synthesis and Characterization of Butyl Acrylate-based Graft Polymers with Thermo-responsive Branching Sites via the Diels-Alder Reaction of Furan/Maleimide
L. Ye (2018)
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