Synthesis and Application of Sequence-controlled Polymers

Liu-qiao Zhang; Zhi-hao Huang; Zheng-biao Zhang; Xiu-lin Zhu

doi:10.11777/j.issn1000-3304.2018.18101

您当前的位置：

首页 >

文章列表页 >

Synthesis and Application of Sequence-controlled Polymers

Feature Articles | 更新时间：2021-01-26

- Synthesis and Application of Sequence-controlled Polymers
- Acta Polymerica Sinica Vol. 0, Issue 9, Pages: 1144-1154(2018)
- 作者机构：
  
  苏州大学材料与化学化工学部　苏州 215123
- 作者简介：
- 基金信息：
- DOI：10.11777/j.issn1000-3304.2018.18101
  CLC：
- Published：2018-9，
  
  Received：9 April 2018，
  
  Revised：2 May 2018，
扫描看全文
Liu-qiao Zhang, Zhi-hao Huang, Zheng-biao Zhang, Xiu-lin Zhu. Synthesis and Application of Sequence-controlled Polymers. [J]. Acta Polymerica Sinica 0(9):1144-1154(2018)
DOI：

Liu-qiao Zhang, Zhi-hao Huang, Zheng-biao Zhang, Xiu-lin Zhu. Synthesis and Application of Sequence-controlled Polymers. [J]. Acta Polymerica Sinica 0(9):1144-1154(2018) DOI： 10.11777/j.issn1000-3304.2018.18101.

摘要

序列可控高分子是指高分子链中不同单体单元按特定顺序排列的高分子. 自然界中的生物大分子，如核酸分子和多肽，其精确的序列结构决定了其复杂功能的表达. 受此启发，序列可控高分子的合成及序列结构与性能关系研究近年来受到了越来越多的关注. 本文介绍了近年来在序列可控高分子合成方面的重要研究成果，突出介绍了本课题组在序列可控高分子方向的研究进展. 最后，对序列可控高分子的应用进行了总结和展望.

Abstract

Sequence-controlled polymers are those with ordered units along their chains. The precision sequence of biological polymers

such as nucleic acid and peptides

plays a crucial role on physiological and sophisticated functions. Inspired by this

the synthesis of sequence-controlled polymers

that is

the placement of specific functional groups at desired positions on the polymer chain

has become one of the ultimate goals of polymer chemists

and received increasing attention in recent years. Up to date

there are a variety of methods to synthesize sequence-controlled polymers based on the step-growth and chain-growth polymerization mechanisms. Compared to the step-growth polymerization

the chain-growth polymerization is much more challenging to achieve sequence-controlled polymers because of the high activity and low propagating selectivity of the growing active center. Therefore

sequence-controlled polymerization is also considered as the " Holy Grail” in the field of polymer synthesis. Although a variety of methods have been developed to regulate polymer sequences

the pursuit of simple and efficient methods toward sequence-controlled polymerization has never stopped. This feature article summarizes the recent progresses on the synthesis of sequence-controlled polymers

and highlights our group’s research in this area. Firstly

we built " supramolecular monomer” by exploiting the weak intermolecular hydrogen-bond interactions to create sequences with alternating feature. We also developed a " latent monomer” strategy based on the temperature-dependent furan/maleimide Diels-Alder reaction

and diverse sequence-controlled polymers were thus readily created. Moreover

a novel chemical route

based on orthogonal chain end deprotection and thiol-maleimide Michael addition

was developed in our group toward the monodisperse and sequence-defined polymers. Finally

the potential applications of the sequence-controlled polymers are also summarized and prospected.

关键词

序列可控高分子可控自由基聚合迭代增长马来酰亚胺Diels-Alder反应

Keywords

Sequence-controlled polymerControlled radical polymerizationIterative growthMaleimideDiels-Alder reaction

references

Lutz J F . Polym Chem , 2010 . 1 ( 1 ): 55 - 62.

Badi N, Lutz J F . Chem Soc Rev , 2009 . 38 ( 12 ): 3383 - 3390.

Nakatani K, Ogura Y, Koda Y, Terashima T, Sawamoto M . J Am Chem Soc , 2012 . 134 ( 9 ): 4373 - 4383.

Matyjaszewski K, Ziegler M J, Arehart S V, Greszta D, Pakula T . J Phys Org Chem , 2000 . 13 ( 12 ): 775 - 786.

Kim J, Mok M M, Sandoval R W, Woo D J, Torkelson J M . Macromolecules , 2006 . 39 ( 18 ): 6152 - 6160.

Luo Y W, Guo Y L, Gao X, Li B G, Xie T . Adv Mater , 2013 . 25 ( 5 ): 743 - 748.

Mok M M, Kim J, Torkelson J M . J Polym Sci, Part B: Polym Phys , 2008 . 46 ( 1 ): 48 - 58.

Aitken B S, Buitrago C F, Heffley J D, Lee M, Gibson H W, Winey K I, Wagener K B . Macromolecules , 2012 . 45 ( 2 ): 681 - 687.

Tan L C, Zhou W H, Huang Y L, Chen Y W . J Macromol Sci B , 2014 . 53 ( 7 ): 1231 - 1243.

Weiss J, Li A, Wischerhoff E, Laschewsky A . Polym Chem , 2012 . 3 ( 2 ): 352 - 361.

Rosales A M, McCulloch B L, Zuckermann R N, Segalman R A . Macromolecules , 2012 . 45 ( 15 ): 6027 - 6035.

Bazzi H S, Bouffard J, Sleiman H F . Macromolecules , 2003 . 36 ( 21 ): 7899 - 7902.

Murnen H K, Khokhlov A R, Khalatur P G, Segalman R A, Zuckermann R N . Macromolecules , 2012 . 45 ( 12 ): 5229 - 5236.

Lutz J F . Macromol Rapid Commun , 2017 . 38 ( 24 ): 1700582 - 1700593.

Matyjaszewski K, Xia J . Chem Rev , 2001 . 101 ( 9 ): 2921 - 2990.

Kamigaito M, Ando T, Sawamoto M . Chem Rev , 2001 . 101 ( 12 ): 3689 - 3746.

Hawker C J, Bosman A W, Harth E . Chem Rev , 2001 . 101 ( 12 ): 3661 - 3688.

Ouchi M, Terashima T, Sawamoto M . Chem Rev , 2009 . 109 ( 11 ): 4963 - 5050.

Moad G, Rizzardo E, Thang S H . Polymer , 2008 . 49 ( 5 ): 1079 - 1131.

Gody G, Maschmeyer T, Zetterlund P B, Perrier S . Nat Commun , 2013 . 4 ( 9 ): 2505 .

Engelis N G, Anastasaki A, Nurumbetov G, Truong N P, Nikolaou V, Shegiwal A, Whittaker M R, Davis T P, Haddleton D M . Nat Chem , 2017 . 9 ( 2 ): 171 - 178.

Anastasaki A, Oschmann B, Willenbacher J, Melker A, van Son M H C, Truong N P, Schulze M W, Discekici E H, McGrath A J, Davis T P, Bates C M, Hawker C J . Angew Chem Int Ed , 2017 . 56 ( 46 ): 14483 - 14487.

Lutz J F, Kirci B, Matyjaszewski K . Macromolecules , 2003 . 36 ( 9 ): 3136 - 3145.

Lutz J F, Pakula T, Matyjaszewski K . ACS Sym Ser , 2003 . 854 ( 19 ): 268 - 282.

Van Steenberge P H M, D'hooge D R, Wang Y, Zhong M J, Reyniers M F, Konkolewicz D, Matyjaszewski K, Marin G B . Macromolecules , 2012 . 45 ( 21 ): 8519 - 8531.

Pakula T, Matyjaszewski K . Macromol Theor Simul , 1996 . 5 ( 5 ): 987 - 1006.

Gray M K, Zhou H Y, Nguyen S T, Torkelson J M . Macromolecules , 2004 . 37 ( 15 ): 5586 - 5595.

Gray M K, Zhou H Y, Nguyen S T, Torkelson J M . Polymer , 2004 . 45 ( 14 ): 4777 - 4786.

Matyjaszewski K . J Macromol Sci Pure , 1997 . A34 ( 10 ): 1785 - 1801.

Lee H I, Matyjaszewski K, Yu S, Sheiko S S . Macromolecules , 2005 . 38 ( 20 ): 8264 - 8271.

Wang L, Broadbelt L J . Macromolecules , 2010 . 43 ( 5 ): 2228 - 2235.

Ercole F, Malic N, Harrisson S, Davis T P, Evans R A . Macromolecules , 2010 . 43 ( 1 ): 249 - 261.

Pfeifer S, Lutz J F . J Am Chem Soc , 2007 . 129 ( 31 ): 9542 - 9543.

Satoh K, Matsuda M, Nagai K, Kamigaito M . J Am Chem Soc , 2010 . 132 ( 29 ): 10003 - 10005.

Hibi Y, Ouchi M, Sawamoto M . Angew Chem Int Ed , 2011 . 50 ( 32 ): 7434 - 7437.

Ida S, Ouchi M, Sawamoto M . J Am Chem Soc , 2010 . 132 ( 42 ): 14748 - 14750.

Ogura Y, Terashima T, Sawamoto M . Polym Chem , 2017 . 8 ( 15 ): 2299 - 2308.

Ogura Y, Artar M, Palmans A R A, Sawamoto M, Meijer E W, Terashima T . Macromolecules , 2017 . 50 ( 8 ): 3215 - 3223.

Yao F J, Liu Q Q, Zhang Z B, Zhu X L . Polymers , 2017 . 9 ( 3 ): 89 - 100.

Zhou Y Y, Liu Q Q, Zhang Z B, Zhu J, Zhu X L . Polym Chem , 2017 . 8 ( 44 ): 6909 - 6916.

Wu H, Wan Y, Wang W, Wang Y, Zhou N, Zhang W, Li X, Zhang Z, Zhu X . Polym Chem , 2015 . 6 ( 14 ): 2620 - 2625.

Zhou X, Wang W, Yu H, Zhao J, Zhang Z, Zhu X . Polym Chem , 2013 . 4 ( 12 ): 3575 - 3581.

Ji Y X, Zhang L Q, Gu X, Zhang W, Zhou N C, Zhang Z B, Zhu X L . Angew Chem Int Ed , 2017 . 56 ( 9 ): 2328 - 2333.

Gu X, Zhang L Q, Li Y, Zhang W, Zhu J, Zhang Z B, Zhu X L . Polym Chem , 2018 . 9 ( 13 ): 1571 - 1576.

Lin F, Wang M Y, Pan Y P, Tang T, Cui D M, Liu B . Macromolecules , 2017 . 50 ( 3 ): 849 - 856.

Liu B, Cui D M, Tang T . Angew Chem Int Ed , 2016 . 55 ( 39 ): 11975 - 11978.

Liu D, Wang M, Wang Z, Wu C, Pan Y, Cui D . Angew Chem Int Ed , 2017 . 56 ( 10 ): 2714 - 2719.

Li J, He J . Acs Macro Lett , 2015 . 4 ( 4 ): 372 - 376.

Zhang Z, You Y Z, Wu D C, Hong C Y . Macromolecules , 2015 . 48 ( 11 ): 3414 - 3421.

Matsumoto S, Kanazawa A, Kanaoka S, Aoshima S . J Am Chem Soc , 2017 . 139 ( 23 ): 7713 - 7716.

Merrifield R B . J Am Chem Soc , 1963 . 85 ( 14 ): 2149 - 2154.

Zuckermann R N, Kerr J M, Kent S B H, Moos W H . J Am Chem Soc , 1992 . 114 ( 26 ): 10646 - 10647.

Porel M, Thornlow D N, Phan N N, Alabi C A . Nat Chem , 2016 . 8 ( 6 ): 590 - 596.

Pfeifer S, Zarafshani Z, Badi N, Lutz J F . J Am Chem Soc , 2009 . 131 ( 26 ): 9195 - 9197.

Porel M, Alabi C A . J Am Chem Soc , 2014 . 136 ( 38 ): 13162 - 13165.

Solleder S C, Meier M A . Angew Chem Int Ed , 2014 . 53 ( 3 ): 711 - 714.

Roy R K, Meszynska A, Laure C, Charles L, Verchin C, Lutz J F . Nat Commun , 2015 . 6 ( 1 ): 7237 - 7244.

Foarta F, Landis C R . J Org Chem , 2016 . 81 ( 22 ): 11250 - 11255.

Hibi Y, Ouchi M, Sawamoto M . Nat Commun , 2016 . 7 ( 1 ): 11064 - 11072.

Wu Y H, Zhang J, Du F S, Li Z C . ACS Macro Lett , 2017 . 6 ( 12 ): 1398 - 1403.

Solleder S C, Wetzel K S, Meier M A . Polym Chem , 2015 . 6 ( 17 ): 3201 - 3204.

Solleder S C, Zengel D, Wetzel K S, Meier M A . Angew Chem Int Ed , 2016 . 55 ( 3 ): 1204 - 1207.

Amir F, Jia Z, Monteiro M J . J Am Chem Soc , 2016 . 138 ( 51 ): 16600 - 16603.

Wang Q, Qu Y, Tian H, Geng Y, Wang F . Macromolecules , 2011 . 44 ( 6 ): 1256 - 1260.

Takizawa K, Nulwala H, Hu J, Yoshinaga K, Hawker C J . J Polym Sci, Part A: Polym Chem , 2008 . 46 ( 18 ): 5977 - 5990.

Barnes J C, Ehrlich D J, Gao A X, Leibfarth F A, Jiang Y, Zhou E, Jamison T F, Johnson J A . Nat Chem , 2015 . 7 ( 10 ): 810 - 815.

Leibfarth F A, Johnson J A, Jamison T F . Proc Natl Acad Sci USA , 2015 . 112 ( 34 ): 10617 - 10622.

Jiang Y, Golder M R, Nguyen H V, Wang Y, Zhong M, Barnes J C, Ehrlich D J, Johnson J A . J Am Chem Soc , 2016 . 138 ( 30 ): 9369 - 9372.

Golder M R, Jiang Y, Teichen P E, Nguyen H V, Wang W, Milos N, Freedman S A, Willard A P, Johnson J A . J Am Chem Soc , 2018 . 140 ( 5 ): 1596 - 1599.

Schumm J S, Pearson D L, Tour J M . Angew Chem Int Ed , 1994 . 33 ( 13 ): 1360 - 1363.

Pearson D L, Schumm J S, Tour J M . Macromolecules , 1994 . 27 ( 8 ): 2348 - 2350.

Sakurai S, Goto H, Yashima E . Org Lett , 2001 . 3 ( 15 ): 2379 - 2382.

Sadighi J P, Singer R A, Buchwald S L . J Am Chem Soc , 1998 . 120 ( 20 ): 4960 - 4976.

Igner E, Paynter O I, Simmonds D J, Whiting M C . J Chem Soc, Perkin Trans 1 , 1987 . 1987 ( 11 ): 2447 - 2454.

Binauld S, Hawker C J, Fleury E, Drockenmuller E . Angew Chem Int Ed , 2009 . 48 ( 36 ): 6654 - 6658.

Jiang X, Lu J, Zhou F, Zhang Z, Pan X, Zhang W, Wang Y, Zhou N, Zhu X . Polym Chem , 2016 . 7 ( 15 ): 2645 - 2651.

Reddy S S, Dong X, Murgasova R, Gusev A I, Hercules D M . Macromolecules , 1999 . 32 ( 5 ): 1367 - 1374.

Hawker C J, Malmström E E, Frank C W, Kampf J P . J Am Chem Soc , 1997 . 119 ( 41 ): 9903 - 9904.

Wooley K L, Hawker C J, Fréchet J M . Angew Chem Int Ed , 1994 . 33 ( 1 ): 82 - 85.

Huang Z, Zhao J, Wang Z, Meng F, Ding K, Pan X, Zhou N, Li X, Zhang Z, Zhu X . Angew Chem Int Ed , 2017 . 56 ( 44 ): 13612 - 13617.

Kleiner R E, Brudno Y, Birnbaum M E, Liu D R . J Am Chem Soc , 2008 . 130 ( 14 ): 4646 - 4659.

Niu J, Hili R, Liu D R . Nat Chem , 2013 . 5 ( 4 ): 282 - 292.

Rosenbaum D M, Liu D R . J Am Chem Soc , 2003 . 125 ( 46 ): 13924 - 13925.

Houshyar S, Keddie D J, Moad G, Mulder R J, Saubern S, Tsanaktsidis J . Polym Chem , 2012 . 3 ( 7 ): 1879 - 1889.

Vandenbergh J, Reekmans G, Adriaensens P, Junkers T . Chem Commun , 2013 . 49 ( 88 ): 10358 - 10360.

Xu J, Shanmugam S, Fu C, Aguey-Zinsou K F, Boyer C . J Am Chem Soc , 2016 . 138 ( 9 ): 3094 - 3106.

Xu J, Fu C, Shanmugam S, Hawker C J, Moad G, Boyer C . Angew Chem Int Ed , 2017 . 56 ( 29 ): 8376 - 8383.

Oh D, Ouchi M, Nakanishi T, Ono H, Sawamoto M . ACS Macro Lett , 2016 . 5 ( 6 ): 745 - 749.

Soejima T, Satoh K, Kamigaito M . J Am Chem Soc , 2016 . 138 ( 3 ): 944 - 954.

Judzewitsch P R, Nguyen T K, Shanmugam S, Wong E H H, Boyer C . Angew Chem Int Ed , 2018 . 57 ( 17 ): 4559 - 4564.

Kuroki A, Sangwan P, Qu Y, Peltier R, Sanchez-Cano C, Moat J, Dowson C G, Williams E G L, Locock K E S, Hartlieb M, Perrier S . ACS Appl Mater Interfaces , 2017 . 9 ( 46 ): 40117 - 40126.

Zhang J L, Deubler R, Hartlieb M, Martin L, Tanaka J, Patyukova E, Topham P D, Schacher F H, Perrier S . Macromolecules , 2017 . 50 ( 18 ): 7380 - 7387.

Washington M A, Swiner D J, Bell K R, Fedorchak M V, Little S R, Meyer T Y . Biomaterials , 2017 . 117 ( 1 ): 66 - 76.

Lawrence J, Goto E, Ren J M, McDearmon B, Kim D S, Ochiai Y, Clark P G, Laitar D, Higashihara T, Hawker C J . J Am Chem Soc , 2017 . 139 ( 39 ): 13735 - 13739.

Norris B N, Zhang S, Campbell C M, Auletta J T, Calvo-Marzal P, Hutchison G R, Meyer T Y . Macromolecules , 2013 . 46 ( 4 ): 1384 - 1392.

Cavallo G, Al Ouahabi A, Oswald L, Charles L, Lutz J F . J Am Chem Soc , 2016 . 138 ( 30 ): 9417 - 9420.

Charles L, Laure C, Lutz J F, Roy R K . Macromolecules , 2015 . 48 ( 13 ): 4319 - 4328.

Laure C, Karamessini D, Milenkovic O, Charles L, Lutz J F . Angew Chem Int Ed , 2016 . 55 ( 36 ): 10722 - 10725.

Karamessini D, Poyer S, Charles L, Lutz J F . Macromol Rapid Commun , 2017 . 38 ( 24 ): 1700426 - 1700430.

Colquhoun H, Lutz J F . Nat Chem , 2014 . 6 ( 6 ): 455 - 456.

Burel A, Carapito C, Lutz J F, Charles L . Macromolecules , 2017 . 50 ( 20 ): 8290 - 8296.

Karamessini D, Petit B E, Bouquey M, Charles L, Lutz J F . Adv Funct Mater , 2017 . 27 ( 3 ): 1604595 - 1604601.

更多指标>

Views

下载量

CSCD

Alert me when the article has been cited

提交

Tools

Publicity Resources

Preparation of Thermally Reversible Silicone Rubber/Carbon Nanotubes Composite with High Electrical Conductivity Based on Diels-Alder Reaction

Synthesis of Thioether Compounds and Their Application in Initiating/Controlling the Radical Polymerization of Styrene

Enzyme Catalysis for RAFT Polymerization and Functionalization: a Sustainable Strategy for Synthesis of Precision Polymers

Synthesis and Healing Behavior of Thermo-reversible Self-healing Epoxy Resins

Preparation of Poly(L-glutamic acid)-based Hydrogels via Diels-Alder Reaction and Study on Their Biomolecule-responsive Properties

Related Author

No data

Related Institution

State Key Laboratory of Organic-Inorganic Composites, Key Laboratory of Carbon Fiber and Functional Polymers, Ministry of Education, Beijing University of Chemical Technology

College of Materials Science and Engineering, Beijing University of Chemical Technology

Institute of Nanochemistry and Nanobiology, Shanghai University

School of Mechatronic Engineering, Lanzhou Jiaotong University

Key Laboratory of Polymer Ecomaterials, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences

Postal code：100190
Tel：010-62588927 Email：gfzxb@iccas.ac.cn
Technical support is provided by Beijing Founder electronics co., LTD 京ICP备05002797号-8 京公网安备11010802024621
It is recommended to read the content of this site in Chrome&IE9+. Please switch to extreme mode in browser 360.
Cookies We use cookies to help provide and enhance our service and tailor content. By continuing, you agree to the use of cookies.

⁰