Comparative Studies on Properties of Polymers with Bulky Side Groups Synthesized by Cyclopolymerization of <italic style="font-style: italic">α</italic>,<italic style="font-style: italic">ω</italic>-Dienes and <italic style="font-style: italic">α</italic>,<italic style="font-style: italic">ω</italic>-Diynes

Shao-Fei Song; Xiao-Yu Liu; Hao Zhang; Zhi-Sheng Fu; Jun-Ting Xu; Zhi-Qiang Fan

doi:10.1007/s10118-019-2183-6

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Comparative Studies on Properties of Polymers with Bulky Side Groups Synthesized by Cyclopolymerization of α,ω-Dienes and α,ω-Diynes

ARTICLE | Updated：2021-02-18

- Comparative Studies on Properties of Polymers with Bulky Side Groups Synthesized by Cyclopolymerization of α,ω-Dienes and α,ω-Diynes
- Chinese Journal of Polymer Science Vol. 37, Issue 2, Pages: 149-156(2019)
- Affiliations：
  
  Ministry of Education Key Laboratory of Macromolecular Synthesis and Functionalization, Department of Polymer Science and Engineering, Zhejiang University, Hangzhou 310027, China
- Author bio：
  
  fanzq@zju.edu.cn
- Funds：
- DOI：10.1007/s10118-019-2183-6
  CLC：
- Received：18 July 2018，
  
  Revised：2018-8-11，
  
  Accepted：19 August 2018，
  
  Online First：10 September 2018，
  
  Published：2019-02
- Accepted：
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Citation: Song, S. F.; Liu, X. Y.; Zhang, H.; Fu, Z. S.; Xu, J. T.; Fan, Z. Q. Comparative studies on properties of polymers with bulky side groups synthesized by cyclopolymerization of α, ω-dienes and α, ω-diynes. Chinese J. Polym. Sci. 2019, 37, 149–156

Shao-Fei Song, Xiao-Yu Liu, Hao Zhang, et al. Comparative Studies on Properties of Polymers with Bulky Side Groups Synthesized by Cyclopolymerization of α,ω-Dienes and α,ω-Diynes[J]. Chinese Journal of Polymer Science, 2019, 37(2): 149-156. DOI: 10.1007/s10118-019-2183-6.
Citation: Song, S. F.; Liu, X. Y.; Zhang, H.; Fu, Z. S.; Xu, J. T.; Fan, Z. Q. Comparative studies on properties of polymers with bulky side groups synthesized by cyclopolymerization of α, ω-dienes and α, ω-diynes. Chinese J. Polym. Sci. 2019, 37, 149–156 DOI： 10.1007/s10118-019-2183-6.

Shao-Fei Song, Xiao-Yu Liu, Hao Zhang, et al. Comparative Studies on Properties of Polymers with Bulky Side Groups Synthesized by Cyclopolymerization of α,ω-Dienes and α,ω-Diynes[J]. Chinese Journal of Polymer Science, 2019, 37(2): 149-156. DOI: 10.1007/s10118-019-2183-6. DOI：

摘要

Abstract

Four polymers containing five-membered rings in the main chain

with or without conjugation structure along the backbone and with or without conjugated pendent groups

were designed and synthesized by metathesis cyclopolymerization of functionalized

-diynes

and cyclopolymerization of functionalized

-dienes catalyzed by the

-diimine palladium-based catalyst

respectively. High to moderate monomer conversions were achieved. Chain structure

molecular weight

and molecular weight distribution (MWD) of the cyclopolymerization products were characterized by

H-

C-NMR

FTIR

and GPC. The polymers showed regular main chain structures

moderately high molecular weight

and narrow MWD. Thermal properties and chain stacking behaviors of the polymers were investigated by differential scanning calorimetry (DSC) and X-ray diffraction (XRD) as well as atomic force microscopy (AFM). The polymer with conjugation system in both the backbone and the pendent groups exhibited UV-Vis absorption at a much longer wavelength than those with the conjugation only in the backbone or only in the side groups. The polymers with conjugated backbone need more space for chain stacking

and the conjugated backbone causes enhanced size of polymer particles assembled from solution. The results showed that primary microstructures of the polymer exerted significant influences on the physical properties.

关键词

Keywords

references

Boaen, N. K.; Hillmyer, M. A . Post-polymerization functionalization of polyolefins . Chem. Soc. Rev. , 2005 . 34 267 - 275 . DOI: 10.1039/b311405h http://doi.org/10.1039/b311405h .

Franssen, N. M. G.; Reek, J. N. H.; de Bruin, B . Synthesis of functional 'polyolefins': State of the art and remaining challenges . Chem. Soc. Rev. , 2013 . 42 5809 - 5832 . DOI: 10.1039/c3cs60032g http://doi.org/10.1039/c3cs60032g .

de Silva, L. C.; Rojas, G.; Schulz, M. D.; Wagener, K. B . Acyclic diene metathesis polymerization: History, methods and applications . Prog. Polym. Sci. , 2017 . 69 79 - 107 . DOI: 10.1016/j.progpolymsci.2016.12.001 http://doi.org/10.1016/j.progpolymsci.2016.12.001 .

Grubbs, R. H . Olefin metathesis . Tetrahedron , 2004 . 60 7117 - 7140 . DOI: 10.1016/j.tet.2004.05.124 http://doi.org/10.1016/j.tet.2004.05.124 .

Hillmyer, M. A.; Grubbs, R. H . Chain transfer in the ring-opening metathesis polymerization of cyclooctadiene using discrete metal alkylidenes . Macromolecules , 1995 . 28 8662 - 8667 . DOI: 10.1021/ma00129a027 http://doi.org/10.1021/ma00129a027 .

Hillmyer, M. A.; Nguyen, S. T.; Grubbs, R. H . Utility of a ruthenium metathesis catalyst for the preparation of end-functionalized polybutadiene . Macromolecules , 1997 . 30 718 - 721 . DOI: 10.1021/ma961316n http://doi.org/10.1021/ma961316n .

Sworen, J. C.; Smith, J. A.; Wagener, K. B.; Baugh, L. S.; Rucker, S. P . Modeling random methyl branching in ethylene/propylene copolymers using metathesis chemistry: Synthesis and thermal behavior . J. Am. Chem. Soc. , 2003 . 125 2228 - 2240 . DOI: 10.1021/ja020862v http://doi.org/10.1021/ja020862v .

Xie, M.; Han, H.; Jin, O.; Du, C . Synthesis of ionic hybrid polymers with polyhedral oligomeric silsesquioxane pendant by acyclic diene metathesis polymerization and characterization . Acta Chim. Sin. , 2013 . 71 1441 - 1445 . DOI: 10.6023/A13040377 http://doi.org/10.6023/A13040377 .

Song, W.; Wu, J.; Yang, G.; Han, H.; Xie, M.; Liao, X . Precisely designed perylene bisimide-substituted polyethylene with a high glass transition temperature and an ordered architecture . RSC Adv. , 2015 . 5 68765 - 68772 . DOI: 10.1039/C5RA10049F http://doi.org/10.1039/C5RA10049F .

Ding, L.; Yang, G.; Xie, M.; Gao, D.; Yu, J.; Zhang, Y . More insight into tandem ROMP and ADMET polymerization for yielding reactive long-chain highly branched polymers and their transformation to functional polymer nanoparticles . Polymer , 2012 . 53 333 - 341 . DOI: 10.1016/j.polymer.2011.12.022 http://doi.org/10.1016/j.polymer.2011.12.022 .

Li, Z. L.; Lv, A.; Li, L.; Deng, X. X.; Zhang, L. J.; Du, F. S.; Li, Z. C . Periodic ethylene-vinyl alcohol copolymers via ADMET polymerization: Synthesis, characterization, and thermal property . Polymer , 2013 . 54 3841 - 3849 . DOI: 10.1016/j.polymer.2013.05.037 http://doi.org/10.1016/j.polymer.2013.05.037 .

Song, S. F.; Guo, W. Q.; Zou, S. F.; Fu, Z. S.; Xu, J. T.; Fan, Z. Q . Polyethylene containing aliphatic ring and aromatic ring defects in the main chain: Synthesis via ADMET and comparisons of thermal properties and crystalline structure . Polymer , 2016 . 107 113 - 121 . DOI: 10.1016/j.polymer.2016.11.017 http://doi.org/10.1016/j.polymer.2016.11.017 .

Song, S. F.; He, F.; Fu, Z. S.; Xu, J. T.; Fan, Z. Q . Precision ADMET polyolefins containing dithiane: Synthesis, thermal properties and macromolecular transformation . J. Polym. Sci., Part A: Polym. Chem. , 2016 . 54 2468 - 2475 . DOI: 10.1002/pola.v54.16 http://doi.org/10.1002/pola.v54.16 .

Teo, Y. C.; Xia, Y . Importance of macromonomer quality in the ring-opening metathesis polymerization of macromonomers . Macromolecules , 2015 . 48 5656 - 5662 . DOI: 10.1021/acs.macromol.5b01176 http://doi.org/10.1021/acs.macromol.5b01176 .

Zou, L.; Long, M.; Zhou, H.; Zhu, W.; Zhang, K.; Chen, Y.; Xi, F . C(sp 3 )-C(sp 3 ) coupling polymerization of alkyl dibromides for preparation of polymers with precisely located phenyl pendants . Polymer , 2015 . 64 196 - 201 . DOI: 10.1016/j.polymer.2015.02.037 http://doi.org/10.1016/j.polymer.2015.02.037 .

Mayershofer, M. G.; Nuyken, O.; Buchmeiser, M. R . Bi- and trinuclear ruthenium alkylidene triggered cyclopolymerization of 1,6-heptadiynes: Access to A n -X-A n block and (A n ) 3 X tristar copolymers . Macromolecules , 2006 . 39 3484 - 3493 . DOI: 10.1021/ma052510p http://doi.org/10.1021/ma052510p .

Vygodskii, Y. S.; Shaplov, A. S.; Lozinskaya, E. I.; Vlasov, P. S.; Malyshkina, I. A.; Gavrilova, N. D.; Kumar, P. S.; Buchmeiser, M. R . Cyclopolymerization of N , N -dipropargylamines and N , N -dipropargyl ammonium salts . Macromolecules , 2008 . 41 1919 - 1928 . DOI: 10.1021/ma7022777 http://doi.org/10.1021/ma7022777 .

Santhosh, P.; Wurst, K.; Buchmeiser, M. R . Factors relevant for the regioselective cyclopolymerization of 1,6-heptadiynes, N , N -dipropargylamines, N , N -dipropargylammonium salts, and dipropargyl ethers by Ru IV -alkylidene-based metathesis initiators . J. Am. Chem. Soc. , 2009 . 131 387 - 395 . DOI: 10.1021/ja804563t http://doi.org/10.1021/ja804563t .

Kang, E. H.; Lee, I. S.; Choi, T. L . Ultrafast cyclopolymerization for polyene synthesis: Living polymerization to dendronized polymers . J. Am. Chem. Soc. , 2011 . 133 11904 - 11907 . DOI: 10.1021/ja204309d http://doi.org/10.1021/ja204309d .

Naumann, S.; Unold, J.; Frey, W.; Buchmeiser, M. R . Regioselective cyclopolymerization of 1,7-octadiynes . Macromolecules , 2011 . 44 8380 - 8387 . DOI: 10.1021/ma201749n http://doi.org/10.1021/ma201749n .

Kang, E. H.; Yu, S. Y.; Lee, I. S.; Park, S. E.; Choi, T. L . Strategies to enhance cyclopolymerization using third-generation Grubbs catalyst . J. Am. Chem. Soc. , 2014 . 136 10508 - 10514 . DOI: 10.1021/ja505471u http://doi.org/10.1021/ja505471u .

Song, W.; Han, H.; Liao, X.; Sun, R.; Wu, J.; Xie, M . Metathesis cyclopolymerization of imidazolium-functionalized 1,6-heptadiyne toward polyacetylene ionomer . Macromolecules , 2014 . 47 6181 - 6188 . DOI: 10.1021/ma501217b http://doi.org/10.1021/ma501217b .

Song, W.; Han, H.; Wu, J.; Xie, M . Ladder-like polyacetylene with excellent optoelectronic properties and regular architecture . Chem. Commun. , 2014 . 50 12899 - 12902 . DOI: 10.1039/C4CC05524A http://doi.org/10.1039/C4CC05524A .

Song, W.; Han, H.; Wu, J.; Xie, M . A bridge-like polymer synthesized by tandem metathesis cyclopolymerization and acyclic diene metathesis polymerization . Polym. Chem. , 2015 . 6 1118 - 1126 . DOI: 10.1039/C4PY01229A http://doi.org/10.1039/C4PY01229A .

Guo, M.; Sun, R.; Han, H.; Wu, J.; Xie, M.; Liao, X . Metathesis cyclopolymerization of 1,6-heptadiyne derivative toward triphenylamine-functionalized polyacetylene with excellent optoelectronic properties and nanocylinder morphology . Macromolecules , 2015 . 48 2378 - 2387 . DOI: 10.1021/acs.macromol.5b00379 http://doi.org/10.1021/acs.macromol.5b00379 .

Kang, E. H.; Kang, C.; Yang, S.; Oks, E.; Choi, T. L . Mechanistic investigations on the competition between the cyclopolymerization and [2 + 2 + 2] cycloaddition of 1,6-heptadiyne derivatives using second-generation Grubbs catalysts . Macromolecules , 2016 . 49 6240 - 6250 . DOI: 10.1021/acs.macromol.6b01110 http://doi.org/10.1021/acs.macromol.6b01110 .

Jung, K.; Kang, E. H.; Sohn, J. H.; Choi, T. L . Highly β -selective cyclopolymerization of 1,6-heptadiynes and ring-closing enyne metathesis reaction using Grubbs Z-selective catalyst: Unprecedented regioselectivity for Ru-based catalysts . J. Am. Chem. Soc. , 2016 . 138 11227 - 11233 . DOI: 10.1021/jacs.6b05572 http://doi.org/10.1021/jacs.6b05572 .

Song, J. A.; Choi, T. L . Seven-membered ring-forming cyclopolymerization of 1,8-nonadiyne derivatives using Grubbs catalysts: Rational design of monomers and insights into the mechanism for olefin metathesis polymerizations . Macromolecules , 2017 . 50 2724 - 2735 . DOI: 10.1021/acs.macromol.7b00606 http://doi.org/10.1021/acs.macromol.7b00606 .

Kang, C.; Kang, E. H.; Choi, T. L . Successful cyclopolymerization of 1,6-heptadiynes using first-generation Grubbs catalyst twenty years after its invention: Revealing a comprehensive picture of cyclopolymerization using Grubbs catalysts . Macromolecules , 2017 . 50 3153 - 3163 . DOI: 10.1021/acs.macromol.7b00488 http://doi.org/10.1021/acs.macromol.7b00488 .

Yang, S.; Shin, S.; Choi, I.; Lee, J.; Choi, T. L . Direct formation of large-area 2D nanosheets from fluorescent semiconducting homopolymer with orthorhombic crystalline orientation . J. Am. Chem. Soc. , 2017 . 139 3082 - 3088 . DOI: 10.1021/jacs.6b12378 http://doi.org/10.1021/jacs.6b12378 .

Kang, C.; Park, H.; Lee, J.; Choi, T. L . Cascade polymerization via controlled tandem olefin metathesis/metallotropic 1,3-shift reactions for the synthesis of fully conjugated polyenynes . J. Am. Chem. Soc. , 2017 . 139 11309 - 11312 . DOI: 10.1021/jacs.7b04913 http://doi.org/10.1021/jacs.7b04913 .

Ivin, K. J.; Mol, J. C. in Olefin metathesis and metathesis polymerization . Academic Press: San Diego, CA, 1997 , 397–410

Yamazaki, M . Industrialization and application development of cyclo-olefin polymer . J. Mol. Catal. A: Chem. , 2004 . 213 81 - 87 . DOI: 10.1016/j.molcata.2003.10.058 http://doi.org/10.1016/j.molcata.2003.10.058 .

Janiak, C.; Lassahn, P. G . The vinyl homopolymerization of norbornene . Macromol. Rapid Commun. , 2001 . 22 479 - 492 . DOI: 10.1002/(ISSN)1521-3927 http://doi.org/10.1002/(ISSN)1521-3927 .

Kesti, M. R.; Coates, G. W.; Waymouth, R. M . Homogeneous Ziegler-Natta polymerization of functionalized monomers catalyzed by cationic Group IV metallocenes . J. Am. Chem. Soc. , 1992 . 114 9679 - 9680 . DOI: 10.1021/ja00050a069 http://doi.org/10.1021/ja00050a069 .

Yamamoto, Y.; Nakagai, Y.; Ohkoshi, N.; Itoh, K . Ruthenium(II)-catalyzed isomer-selective cyclization of 1,6-dienes leading to exo-methylenecyclo-pentanes: Unprecedented cycloisomerization mechanism involving ruthenacyclopentane(hydrido) intermediate . J. Am. Chem. Soc. , 2001 . 123 6372 - 6380 . DOI: 10.1021/ja010134s http://doi.org/10.1021/ja010134s .

Park, S.; Takeuchi, D.; Osakada, K . Pd complex-promoted cyclopolymerization of functionalized α , ω -dienes and copolymerization with ethylene to afford polymers with cyclic repeating units . J. Am. Chem. Soc. , 2006 . 128 3510 - 3511 . DOI: 10.1021/ja058408p http://doi.org/10.1021/ja058408p .

Takeuchi, D.; Matsuura, R.; Park, S.; Osakada, K . Cyclopolymerization of 1,6-heptadienes catalyzed by iron and cobalt complexes: Synthesis of polymers with trans - or cis -fused 1,2-cyclopentanediyl groups depending on the catalyst . J. Am. Chem. Soc. , 2007 . 129 7002 - 7003 . DOI: 10.1021/ja0718568 http://doi.org/10.1021/ja0718568 .

Takeuchi, D.; Fukuda, Y.; Park, S.; Osakada, K . Cyclopolymerization of 9, 9-diallylfluorene promoted by Ni complexes. Stereoselective formation of six- and five-membered rings during the polymer growth . Macromolecules , 2009 . 42 5909 - 5912 . .

Takeuchi, S.; Matsuura, R.; Fukuda, Y.; Osakada, K . Selective cyclopolymerization of α , ω -dienes and copolymerization with ethylene catalyzed by Fe and Co complexes . Dalton Trans. , 2009 . 8955 - 8962 . .

Okada, T . Cyclopolymerization of monoterminal 1,6-dienes catalyzed by Pd complexes . Macromolecules , 2010 . 43 7998 - 8006 . DOI: 10.1021/ma101146j http://doi.org/10.1021/ma101146j .

Takeuchi, D . Novel controlled polymerization of cyclo-olefins, dienes, and trienes by utilizing reaction properties of late transition metals . Macromol. Chem. Phys. , 2011 . 212 1545 - 1551 . DOI: 10.1002/macp.v212.15 http://doi.org/10.1002/macp.v212.15 .

Motokuni, K.; Takeuchi, D.; Osakada, K . Double cyclopolymerization of monoterminal trienes using Pd catalysis. Polymers containing functionallized cyclic groups with a regulated sequence . Macromolecules , 2014 . 47 6522 - 6526 . .

Takeuchi, D.; Watanabe, K.; Sogo, K.; Osakada, K . Polymerization of methylenecyclohexanes catalyzed by diimine-Pd complex. Polymers having trans - or cis -1,4- and trans -1,3-cyclohexylene groups . Organometallics , 2015 . 34 3007 - 3011 . DOI: 10.1021/acs.organomet.5b00313 http://doi.org/10.1021/acs.organomet.5b00313 .

Takeuchi, D.; Watanabe, K.; Osakada, K . Synthesis of polyketones containing substituted six-membered rings via Pd-catalyzed copolymerization of methylenecyclohexanes with carbon monoxide . Macromolecules , 2015 . 48 6745 - 6749 . DOI: 10.1021/acs.macromol.5b01458 http://doi.org/10.1021/acs.macromol.5b01458 .

Motokuni, K.; Haupler, B.; Burges, R.; Hager, M. D.; Schubert, U. S . Synthesis and electrochemical properties of novel redox-active polymers with anthraquinone moieties by Pd-catalyzed cyclopolymerization of dienes . J. Polym. Sci., Part A: Polym. Chem. , 2016 . 54 2184 - 2190 . DOI: 10.1002/pola.v54.14 http://doi.org/10.1002/pola.v54.14 .

Kang, S. K.; Baik, T. G.; Kulak, A. N.; Ha, Y. H.; Lim, Y.; Park, J . Palladium-catalyzed carbocyclization/silastannylation and distannylation of bis(allenes) . J. Am. Chem. Soc. , 2000 . 122 11529 - 11530 . DOI: 10.1021/ja001597l http://doi.org/10.1021/ja001597l .

Aitken, B. S.; Wieruszewski, P. M.; Graham, K. R.; Reynolds, J. R.; Wagener, K. B . Perfectly regioregular electroactive polyolefins: Impact of inter-chromophore distance on PLED EQE . Macromolecules , 2012 . 45 705 - 712 . DOI: 10.1021/ma202409k http://doi.org/10.1021/ma202409k .

Halbach, T. S.; Krause, J. O.; Nuyken, O.; Buchmeiser, M. R . Stereoselective cyclopolymerization of polar 1,6-heptadiynes by novel, tailor-made ruthenium-based metathesis catalysts . Macromol. Rapid Commun. , 2005 . 26 784 - 790 . DOI: 10.1002/(ISSN)1521-3927 http://doi.org/10.1002/(ISSN)1521-3927 .

Kim, S. H.; Kim, Y. H.; Cho, H. N.; Kwon, S. K.; Kim, H. K.; Choi, S. K . Unusual optical absorption behavior, polymer structure, and air stability of poly(1,6-heptadiyne)s with substituents at the 4-position . Macromolecules , 1996 . 29 5422 - 5426 . DOI: 10.1021/ma9507103 http://doi.org/10.1021/ma9507103 .

Rojas, G.; Inci, B.; Wei, Y.; Wagener, K. B . Precision polyethylene: Changes in morphology as a function of alkyl branch size . J. Am. Chem. Soc. , 2009 . 131 17376 - 17386 . DOI: 10.1021/ja907521p http://doi.org/10.1021/ja907521p .

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Comparative Studies on Properties of Polymers with Bulky Side Groups Synthesized by Cyclopolymerization of α,ω-Dienes and α,ω-Diynes

DOI：10.1007/s10118-019-2183-6

摘要

Abstract

关键词

Keywords

references