
1.Beijing Key Laboratory of Construction Tailorable Advanced Functional Materials and Green Applications, School of Materials Science and Engineering, Beijing Institute of Technology, Beijing 100081, China
bing@bit.edu.cn (J.B.S.)
chdongyp@bit.edu.cn (Y.P.D.)
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Wei-Qiang Fu, Gui-Nan Zhu, Jian-Bing Shi, et al. Synthesis and Properties of Photodegradable Poly(furan-amine)s by a Catalyst-free Multicomponent Cyclopolymerization. [J]. Chinese Journal of Polymer Science 37(10):981-989(2019)
Wei-Qiang Fu, Gui-Nan Zhu, Jian-Bing Shi, et al. Synthesis and Properties of Photodegradable Poly(furan-amine)s by a Catalyst-free Multicomponent Cyclopolymerization. [J]. Chinese Journal of Polymer Science 37(10):981-989(2019) DOI: 10.1007/s10118-019-2281-5.
A series of new photodegradable poly(furan-amine)s (PFAs) were synthesized by a one-pot, catalyst-free, multicomponent cyclopolymerization between diisocyanides, dialkylacetylene dicarboxylates, and aromatic dialdehydes. All polymerizations were conducted in toluene at 100 °C for 6 h without inert gas protection and furnished polymers with a satisfactory molecular weight (,M,w, up to 32200) and yield. The PFA structure was confirmed by spectroscopic techniques, such as GPC, FTIR, and NMR, as well as by comparison with a model compound. The polymers exhibited good solubility in common organic solvents and thermal stability. All the PFAs had high refractive indices in the visible light region (400 nm to 800 nm). Moreover, the PFAs were substantially degraded by UV irradiation due to the presence of furan rings. The film thickness reduction rate could be over 90%.
PhotodegradationMulticomponent reactionCatalyst-free polymerization
Nayanathara, U.; Kottegoda, N.; Perera, I. C.; Mudiyanselage, T. K . Synthesis, photodegradable and antibacterial properties of polystyrene-cinnamaldehyde copolymer film . Polym. Degrad. Stab. , 2018 . 155 195 -207 . DOI:10.1016/j.polymdegradstab.2018.07.021http://doi.org/10.1016/j.polymdegradstab.2018.07.021 .
Pan, G. Y.; Jia, H. R.; Zhu, Y. X.; Wu, F. G . Turning double hydrophilic into amphiphilic: IR825-conjugated polymeric nanomicelles for near-infrared fluorescence imaging-guided photothermal cancer therapy . Nanoscale , 2018 . 10 2115 -2127 . DOI:10.1039/C7NR07495Fhttp://doi.org/10.1039/C7NR07495F .
Fairbanks, B. D.; Singh, S. P.; Bowman, C. N.; Anseth, K. S . Photodegradable, photoadaptable hydrogels via radical-mediated disulfide fragmentation reaction . Macromolecules , 2011 . 44 2444 -2450 . DOI:10.1021/ma200202whttp://doi.org/10.1021/ma200202w .
Cao, Z.; Li, Q.; Wang, G . Photodegradable polymer nanocapsules fabricated from dimethyldiethoxysilane emulsion templates for controlled release . Polym. Chem. , 2017 . 8 6817 -6823 . DOI:10.1039/C7PY01153Ahttp://doi.org/10.1039/C7PY01153A .
Käpyla, E.; Delgado, S. M.; Kasko, A. M . Shape-changing photodegradable hydrogels for dynamic 3D cell culture . ACS Appl. Mater. Interfaces , 2016 . 8 17885 -17893 . DOI:10.1021/acsami.6b05527http://doi.org/10.1021/acsami.6b05527 .
McKinnon, D. D.; Brown, T. E.; Kyburz, K. A.; Kiyotake, E.; Anseth, K. S . Design and characterization of a synthetically accessible, photodegradable hydrogel for user-directed formation of neural networks . Biomacromolecules , 2014 . 15 2808 -2816 . DOI:10.1021/bm500731bhttp://doi.org/10.1021/bm500731b .
Manouras, T.; Vamvakaki, M . Field responsive materials: Photo-, electro-, magnetic- and ultrasound-sensitive polymers . Polym. Chem. , 2017 . 8 74 -96 . DOI:10.1039/C6PY01455Khttp://doi.org/10.1039/C6PY01455K .
Yang, F. C.; Wang, J.; Chen, L.; Wang, X.; Chen, X. Y.; Zhang, X . Soluble and degradable polyimides with phenyl-2-pyridyl ether structure: Synthesis and characterization . Chinese J. Polym. Sci. , 2015 . 33 481 -489 . DOI:10.1007/s10118-015-1602-6http://doi.org/10.1007/s10118-015-1602-6 .
Liu, Y.; Yuan, J.; Zou, Y.; Li, Y . Research progress of the furan-containing fused ring conjugated organic molecules and polymers . Acta Chim. Sin. , 2017 . 75 257 -270 . DOI:10.6023/A16090495http://doi.org/10.6023/A16090495 .
Hu, Y.; Han, T.; Yan, N.; Liu, J.; Liu, X.; Wang, W. X.; Lam, J. W. Y.; Tang B. Z . Visualization of biogenic amines and in vivo ratiometric mapping of intestinal pH by AIE-active polyheterocycles synthesized by metal-free multicomponent polymerizations . Adv. Funct. Mater. , 2019 . 1902240 DOI:10.1002/adfm.201902240http://doi.org/10.1002/adfm.201902240 .
Wang, F.; Gu, H.; Swager, T. M . Carbon nanotube/polythiophene chemiresistive sensors for chemical warfare agents . J. Am. Chem. Soc. , 2008 . 130 5392 -5393 . DOI:10.1021/ja710795khttp://doi.org/10.1021/ja710795k .
Afzal, A.; Abuilaiwi, F. A.; Habib, A.; Awais, M.; Waje, S. B.; Atieh, M. A . Polypyrrole/carbon nanotube supercapacitors: Technological advances and challenges . J. Power Sources , 2017 . 352 174 -186 . DOI:10.1016/j.jpowsour.2017.03.128http://doi.org/10.1016/j.jpowsour.2017.03.128 .
Tibaoui, T.; Zaidi, B.; Bouachrine, M.; Paris, M.; Alimi, K . A study of polymers obtained by oxidative coupling of furan monomers . Synth. Met. , 2011 . 161 2220 -2225 . DOI:10.1016/j.synthmet.2011.07.007http://doi.org/10.1016/j.synthmet.2011.07.007 .
Yeh, I. C.; Rinderspacher, B. C.; Andzelm, J. W.; Cureton, L. T.; La Scala, J . Computational study of thermal and mechanical properties of nylons and bio-based furan polyamides . Polymer , 2014 . 55 166 -174 . DOI:10.1016/j.polymer.2013.11.009http://doi.org/10.1016/j.polymer.2013.11.009 .
Streifel, B. C.; Martínez Hardigree, J. F.; Katz, H. E.; Tovar, J. D . Heteroaromatic variation in amorphous 1,6-methano[10]annulene-based charge-transporting organic semiconductors . J. Mater. Chem. C , 2014 . 2 7851 -7858 . DOI:10.1039/C4TC01326Chttp://doi.org/10.1039/C4TC01326C .
Sousa, A. F.; Vilela, C.; Fonseca, A. C.; Matos, M.; Freire, C. S. R.; Gruter, G. J. M.; Coelho, J. F. J.; Silvestre, A. J. D . Biobased polyesters and other polymers from 2,5-furandicarboxylic acid: A tribute to furan excellency . Polym. Chem. , 2015 . 6 5961 -5983 . DOI:10.1039/C5PY00686Dhttp://doi.org/10.1039/C5PY00686D .
Kaur, S.; Findlay, N. J.; Coomer, F. C.; Berridge, R.; Skabara, P. J . Poly([1,4]dithiino[2,3-c]furan): The synthesis, electrochemistry, and optoelectronic properties of a furan-containing polymer . Macromol. Rapid Commun. , 2013 . 34 1330 -1334 . DOI:10.1002/marc.v34.16http://doi.org/10.1002/marc.v34.16 .
Song, B.; Hu, K.; Qin, A.; Tang, B. Z . Oxygen as a crucial comonomer in alkyne-based polymerization toward functional poly(tetrasubstituted furan)s . Macromolecules , 2018 . 51 7013 -7018 . DOI:10.1021/acs.macromol.8b01293http://doi.org/10.1021/acs.macromol.8b01293 .
Deng, H.; Hu, R. Zhao, E.; Chan, C. Y. K.; Lam, J. W. Y.; Tang, B. Z . One-pot three-component tandem polymerization toward functional poly(arylene thiophenylene) with aggregation-enhanced emission characteristics . Macromolecules , 2014 . 47 4920 -4929 . DOI:10.1021/ma501190ghttp://doi.org/10.1021/ma501190g .
Huang, Y.; Chen, P.; Wei, B.; Hu, R.; Tang, B. Z . Aggregation-induced emission-active hyperbranched poly(tetrahydropyrimidine)s synthesized from multicomponent tandem polymerization . Chinese J. Polym. Sci. , 2019 . 37 428 -436 . DOI:10.1007/s10118-019-2230-3http://doi.org/10.1007/s10118-019-2230-3 .
Hu, R.; Li, W.; Tang, B. Z . Recent advances in alkyne-based multicomponent polymerizations . Macromol. Chem. Phys. , 2016 . 217 213 -224 . DOI:10.1002/macp.201500291http://doi.org/10.1002/macp.201500291 .
Kayser, L, V.; Vollmer, M.; Welnhofer, M.; Krikcziokat, H.; Meerholz, K.; Arndtsen, B, A . Metal-free, multicomponent synthesis of pyrrole-based π-conjugated polymers from imines, acid chlorides, and alkynes . J. Am. Chem. Soc. , 2016 . 138 10516 -10521 . DOI:10.1021/jacs.6b05035http://doi.org/10.1021/jacs.6b05035 .
Fu, W.; Dong, L.; Shi, J.; Tong, B.; Cai, Z.; Zhi, J.; Dong, Y . Synthesis of polyquinolines via one-pot polymerization of alkyne, aldehyde, and aniline under metal-free catalysis and their properties . Macromolecules , 2018 . 51 3254 -3263 . DOI:10.1021/acs.macromol.7b02494http://doi.org/10.1021/acs.macromol.7b02494 .
Liu, Y.; Qin, A.; Tang, B. Z . Polymerizations based on triple-bond building blocks . Prog. Polym. Sci. , 2018 . 78 92 -138 . DOI:10.1016/j.progpolymsci.2017.09.004http://doi.org/10.1016/j.progpolymsci.2017.09.004 .
Fu, W.; Dong, L.; Shi, J.; Tong, B.; Cai, Z.; Zhi J.; Dong, Y . Multicomponent spiropolymerization of diisocyanides, alkynes and carbon dioxide for constructing 1,6-dioxospiro[4,4]nonane-3,8-diene as structural units under one-pot catalyst-free conditions . Polym. Chem. , 2018 . 9 5543 -5550 . DOI:10.1039/C8PY01336Ehttp://doi.org/10.1039/C8PY01336E .
Deng, X. X.; Li, L.; Li, Z. L.; Lv, A.; Du, F. S.; Li, Z. C . Sequence regulated poly(ester-amide)s based on passerini reaction . ACS Macro Lett. , 2012 . 1 1300 -1303 . DOI:10.1021/mz300456phttp://doi.org/10.1021/mz300456p .
Fu, W.; Kong, L.; Shi, J.; Tong, B.; Cai, Z.; Zhi J.; Dong, Y . Synthesis of poly(amine-furan-arylene)s through a one-pot catalyst-free in situ cyclopolymerization of diisocyanide, dialkylacetylene dicarboxylates and dialdehyde . Macromolecules , 2019 . 52 729 -737 . DOI:10.1021/acs.macromol.8b02251http://doi.org/10.1021/acs.macromol.8b02251 .
Mao, L.; Sakurai, H.; Hirao, T . Facile synthesis of 2,3-disubstituted quinoxalines by Suzuki-Miyaura coupling . Synthesis , 2004 . 15 2535 -2539. .
Sandmann, B.; Happ, B.; Vitz, J.; Paulus, R. M.; Hager, M. D.; Burtscher, P.; Moszner, N.; Schubert, U. S . Metal-free cycloaddition of internal alkynes and multifunctional azides under solvent-free conditions . Macromol. Chem. Phys. , 2014 . 215 1603 -1608 . DOI:10.1002/macp.v215.17http://doi.org/10.1002/macp.v215.17 .
Song, B.; He, B.; Qin, A.; Tang, B. Z . Direct polymerization of carbon dioxide, diynes, and alkyl dihalides under mild reaction conditions . Macromolecules , 2018 . 51 42 -48 . DOI:10.1021/acs.macromol.7b02109http://doi.org/10.1021/acs.macromol.7b02109 .
Wei, B.; Li, W.; Zhao, Z.; Qin, A.; Hu, R.; Tang, B. Z . Metal-free multicomponent tandem polymerizations of alkynes, amines, and formaldehyde toward structure- and sequence- controlled luminescent polyheterocycles . J. Am. Chem. Soc. , 2017 . 139 5075 -5084 . DOI:10.1021/jacs.6b12767http://doi.org/10.1021/jacs.6b12767 .
Alizadeh, A.; Rostamnia, S.; Zhu, L. G . Competition of the R3P/DAAD and RNC/DAAD zwitterions in their production and reaction with aromatic carboxylic acids: A novel binucleophilic system for three-component synthesis of 2-aminofurans . Synthesis , 2008 . 2008 (11 ):1788 -1792 . DOI:10.1055/s-2008-1067028http://doi.org/10.1055/s-2008-1067028 .
Urdl, K.; Weiss, S.; Karpa, A.; Perić, M.; Zikulnig-Rusch, E.; Brecht, M.; Kandelbauer, A.; Müller, U.; Kern, W . Furan-functionalised melamine-formaldehyde particles performing Diels-Alder reactions . Eur. Polym. J. , 2018 . 108 225 -234 . DOI:10.1016/j.eurpolymj.2018.08.023http://doi.org/10.1016/j.eurpolymj.2018.08.023 .
Suzuki, Y . Synthesis and characterization of high refractive index and high Abbe’s number poly(thioether sulfone)s based on tricyclo[5.2.1.02,6]decane moiety . Macromolecules , 2012 . 45 3402 -3408 . DOI:10.1021/ma300379whttp://doi.org/10.1021/ma300379w .
Cai, Z.; Zhang, Y.; Song, Y.; Cheng, Q.; Zheng, Y.; Cui, Z.; Shi, Z.; Chen, C.; Zhang, D . Optically transparent fluorine-containing polycarbonates with high refractive indices for thermo-optic switches . Mater. Chem. Front. , 2017 . 1 2031 -2038 . DOI:10.1039/C7QM00209Bhttp://doi.org/10.1039/C7QM00209B .
Faurie, A.; Mallet, C.; Allain, M.; Skene, W. G.; Frère, P . Topological and packing mode modification for solid-state emission enhancement of bis(perfluorostyryl)furan derivatives . New J. Chem. , 2016 . 40 6728 -6734 . DOI:10.1039/C5NJ03561Ahttp://doi.org/10.1039/C5NJ03561A .
Qiu, Z.; Liu, X.; Lam, J. W. Y.; Tang, B. Z . The marriage of aggregation-induced emission with polymer science . Macromol. Rapid Commun. , 2019 . 40 1800568 DOI:10.1002/marc.201800568http://doi.org/10.1002/marc.201800568 .
Hu, R.; Xin, D. H.; Qin, A. J.; Tang, B. Z . Polymers with aggregation-induced emission characteristics . Acta Polymerica Sinica (in Chinese) , 2018 . 132 -144. .
Dong, H.; Zhu, H.; Meng, Q.; Gong, X.; Hu, W . Organic photoresponse materials and devices . Chem. Soc. Rev. , 2012 . 41 1754 -1808 . DOI:10.1039/C1CS15205Jhttp://doi.org/10.1039/C1CS15205J .
Yildirim, Y . Influence of γ-ray irradiation on the thermal stability and conductivity of polyfuran . Asian J. Chem. , 2013 . 25 7582 -7586 . DOI:10.14233/ajchemhttp://doi.org/10.14233/ajchem .
Christensen, E.; Fioroni, G. M.; Kim, S.; Fouts, L.; Gjersing, E.; Paton, R. S.; McCormick, R. L . Experimental and theoretical study of oxidative stability of alkylated furans used as gasoline blend components . Fuel , 2018 . 212 576 -585 . DOI:10.1016/j.fuel.2017.10.066http://doi.org/10.1016/j.fuel.2017.10.066 .
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