Supporting Information
General descriptions of materials and methods, the syntheses of the obtained compounds (5, 7a,b, 9a,b, 10a,b, 11a–c, 12a–c, 13a–c, 14a–c, 15, 16, 17) as well as analytical data (1H and 13C NMR, FTIR and EIMS analyses) of these compounds and copies of 1H and 13C NMR spectra of compounds (10a,b, 14a–c, 17) plus the 1H NMR spectra of compounds (5, 7a, 7b, 9a, 9b, 12c, 13a–c, 16) are given.
| Supporting Information File 1: Experimental part. | ||
| Format: PDF | Size: 1.3 MB | Download |
Cite the Following Article
Investigations of thiol-modified phenol derivatives for the use in thiol–ene photopolymerizations
Sebastian Reinelt, Monir Tabatabai, Urs Karl Fischer, Norbert Moszner, Andreas Utterodt and Helmut Ritter
Beilstein J. Org. Chem. 2014, 10, 1733–1740.
https://doi.org/10.3762/bjoc.10.180
How to Cite
Reinelt, S.; Tabatabai, M.; Fischer, U. K.; Moszner, N.; Utterodt, A.; Ritter, H. Beilstein J. Org. Chem. 2014, 10, 1733–1740. doi:10.3762/bjoc.10.180
Download Citation
Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window
below.
Citation data in RIS format can be imported by all major citation management software, including EndNote,
ProCite, RefWorks, and Zotero.
Citations to This Article
Up to 20 of the most recent references are displayed here.
Scholarly Works
- He, C.; Zhou, J.; Pan, X.; Tan, Q.; Ren, J.; Li, J. Biphenylation, ester-free and stepwise reaction strategy of thiol-epoxy crosslinking network for durable thermally and hygrothermally resistant electronic packaging. Chemical Engineering Journal 2025, 162891. doi:10.1016/j.cej.2025.162891
- He, C.; Li, L.; Sun, Y.; Wang, X.; Ren, J.; Li, J. Enhanced durability of a novel thiol-epoxy network thermosets with excellent hygrothermal and chemical resistance. Chinese Chemical Letters 2025, 36, 110905. doi:10.1016/j.cclet.2025.110905
- Sinawehl, L.; Wolff, R.; Koch, T.; Stampfl, J.; Liska, R.; Baudis, S. Photopolymers Based on Boronic Esters for the Enhanced Degradation of 3D-Printed Scaffolds. ACS Applied Polymer Materials 2023, 5, 5758–5771. doi:10.1021/acsapm.3c01000
- Sommer, K.; Rieger, P.; Müller, S. M.; Schwarz, R.; Trimmel, G.; Feuchter, M.; Griesser, T. 3D Printing of Dual‐Cure Networks Based on (Meth)acrylate/Bispropargyl Ether Building Blocks. Advanced Engineering Materials 2022, 25. doi:10.1002/adem.202200901
- Dellago, B.; Altun, A. A.; Liska, R.; Baudis, S. Exploring the limits of toughness enhancers for 3D printed photopolymers as bone replacement materials. Journal of Polymer Science 2022, 61, 143–154. doi:10.1002/pol.20220378
- Thiounn, T.; Karunarathna, M. S.; Slann, L. M.; Lauer, M. K.; Smith, R. C. Sequential crosslinking for mechanical property development in high sulfur content composites. Journal of Polymer Science 2020, 58, 2943–2950. doi:10.1002/pol.20200521
- Arslan, M.; Pulido, B. A.; Nunes, S. P.; Yagci, Y. Functionalization of Poly(oxindole biphenylylene) membranes by photoinduced thiol-yne click chemistry. Journal of Membrane Science 2020, 598, 117673. doi:10.1016/j.memsci.2019.117673
- Arseneault, M.; Granskog, V.; Khosravi, S.; Heckler, I.; Mesa-Antunez, P.; Hult, D.; Zhang, Y.; Malkoch, M. The Dawn of Thiol-Yne Triazine Triones Thermosets as a New Material Platform Suited for Hard Tissue Repair. Advanced materials (Deerfield Beach, Fla.) 2018, 30, 1804966. doi:10.1002/adma.201804966
- Granskog, V.; García-Gallego, S.; von Kieseritzky, J.; Rosendahl, J.; Stenlund, P.; Zhang, Y.; Petronis, S.; Lyvén, B.; Arner, M.; Håkansson, J.; Malkoch, M. High-Performance Thiol–Ene Composites Unveil a New Era of Adhesives Suited for Bone Repair. Advanced Functional Materials 2018, 28, 1800372. doi:10.1002/adfm.201800372
- Fei, Z.; Wang, T.; Fan, P.; Chen, F.; Zhong, M. Facile Preparation of Crosslinked PAN Membranes Based on Thiol-Ene Photopolymerization. Polymers 2017, 9, 390. doi:10.3390/polym9090390
- Oesterreicher, A.; Moser, A.; Edler, M.; Griesser, H.; Schlögl, S.; Pichelmayer, M.; Griesser, T. Investigating Photocurable Thiol‐Yne Resins for Biomedical Materials. Macromolecular Materials and Engineering 2017, 302, 1600450. doi:10.1002/mame.201600450
- Blasco, E.; Wegener, M.; Barner-Kowollik, C. Photochemically Driven Polymeric Network Formation: Synthesis and Applications. Advanced materials (Deerfield Beach, Fla.) 2017, 29, 1604005. doi:10.1002/adma.201604005
- Oesterreicher, A.; Ayalur-Karunakaran, S.; Moser, A.; Mostegel, F.; Edler, M.; Kaschnitz, P.; Pinter, G.; Trimmel, G.; Schlögl, S.; Griesser, T. Exploring thiol‐yne based monomers as low cytotoxic building blocks for radical photopolymerization. Journal of Polymer Science Part A: Polymer Chemistry 2016, 54, 3484–3494. doi:10.1002/pola.28239
- Kowalewska, A. B.; Nowacka, M.; Maniukiewicz, W. Octa(3-mercaptopropyl)octasilsesquioxane – A reactive nanocube of unique self-assembled packing morphology. Journal of Organometallic Chemistry 2016, 810, 15–24. doi:10.1016/j.jorganchem.2016.02.040
- Oesterreicher, A.; Wiener, J.; Roth, M.; Moser, A.; Gmeiner, R.; Edler, M.; Pinter, G.; Griesser, T. Tough and degradable photopolymers derived from alkyne monomers for 3D printing of biomedical materials. Polymer Chemistry 2016, 7, 5169–5180. doi:10.1039/c6py01132b
- Podgórski, M.; Becka, E.; Claudino, M.; Flores, A.; Shah, P. K.; Stansbury, J. W.; Bowman, C. N. Ester-free thiol–ene dental restoratives—Part B: Composite development. Dental materials : official publication of the Academy of Dental Materials 2015, 31, 1263–1270. doi:10.1016/j.dental.2015.08.147
- Roth, M.; Oesterreicher, A.; Mostegel, F.; Moser, A.; Pinter, G.; Edler, M.; Piock, R.; Griesser, T. Silicon‐based mercaptans: High‐performance monomers for thiol‐ene photopolymerization. Journal of Polymer Science Part A: Polymer Chemistry 2015, 54, 418–424. doi:10.1002/pola.27792
- Podgórski, M.; Becka, E.; Chatani, S.; Claudino, M.; Bowman, C. N. Ester-free thiol-X resins: new materials with enhanced mechanical behavior and solvent resistance. Polymer chemistry 2015, 6, 2234–2240. doi:10.1039/c4py01552e
Patents
- NAIR KAMLESH; THOMAS DAVID B. Functionalized poly(aryl ether sulfones) copolymers. US 12157797 B2, Dec 3, 2024.
- CHEN CHANGJING; LIU TAO; LIN HONGTENG; LI SHUAI. Polymercaptan compound and preparation method thereof, curing agent, resin composition and use thereof. US 11919842 B2, March 5, 2024.
- LI JIANBO; PAN XUEYI. Dual-curing resin composition resistant to damp-heat hydrolysis as well as preparation method and application of dual-curing resin composition. CN 115232259 A, Oct 25, 2022.
- LI JIANBO; WANG XINYU. Moisture-heat hydrolysis resistant single-component epoxy resin composition as well as preparation method and application thereof. CN 115232585 A, Oct 25, 2022.
- LI JIANBO; CHEN MENGJIA. Ultraviolet curing resin composition based on thiol-ene reaction as well as preparation method and application of ultraviolet curing resin composition. CN 115093567 A, Sept 23, 2022.
- NAIR KAMLESH. SIDE-CHAIN FUNCTIONALIZED POLY(ARYL ETHER SULFONES) COPOLYMER COMPRISING REACTIVE END-GROUPS. WO 2021123405 A1, June 24, 2021.
- NAIR KAMLESH; THOMAS DAVID B. FUNCTIONALIZED POLY(ARYL ETHER SULFONES) COPOLYMERS. WO 2020187684 A1, Sept 24, 2020.
- MOSZNER NORBERT; BURTSCHER PETER; FISCHER URS-KARL; RITTER HELMUT; TABATABAI MONIR; UTTERODT ANDREAS. Dental materials based on low-odour thiols. US 9877898 B2, Jan 30, 2018.
- MOSZNER NORBERT; BURTSCHER PETER; FISCHER URS-KARL; RITTER HELMUT; TABATABAI MONIR; UTTERODT ANDREAS. DENTAL MATERIALS BASED ON LOW-ODOUR THIOLS. US 20170007505 A1, Jan 12, 2017.
