Synlett 2022; 33(09): 863-874
DOI: 10.1055/a-1703-2608
cluster
Mechanochemistry

Heterocyclic Mechanophores in Polymer Mechanochemistry

Sangmin Jung
,
Hyo Jae Yoon
This work was supported by the National Research Foundation of Korea (NRF-2019R1A2C2011003, NRF-2019R1A6A1A11044070, and NRF-2021M3F3A2A03017999).


Abstract

This Account covers the recent progress made on heterocyclic mechanophores in the field of polymer mechanochemistry. In particular, the types of such mechanophores as well as the mechanisms and applications of their force-induced structural transformations are discussed and related perspectives and future challenges proposed.

1 Introduction

2 Types of Mechanophores

3 Methods to Incorporate Heterocycle Mechanophores into Polymer Systems

4 Mechanochemical Reactions of Heterocyclic Mechanophores

4.1 Three-Membered-Ring Mechanophores

4.2 Four-Membered-Ring Mechanophores

4.3 Six-Membered-Ring Mechanophores

4.4 Bicyclic Mechanophores

5 Applications

5.1 Cross-Linking of Polymer

5.2 Degradable Polymer

5.3 Mechanochromic Polymer

6 Concluding Remarks and Outlook



Publication History

Received: 28 October 2021

Accepted after revision: 22 November 2021

Accepted Manuscript online:
22 November 2021

Article published online:
05 January 2022

© 2021. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 
  • References

  • 1 Sandoval-Torrientes R, Carr TR, De Bo G. Macromol. Rapid Commun. 2021; 42: 2000447
  • 2 Chen Y, Spiering AJ. H, Karthikeyan S, Peters GW. M, Meijer EW, Sijbesma RP. Nat. Chem. 2012; 4: 559
  • 3 Davis DA, Hamilton A, Yang J, Cremar LD, Van Gough D, Potisek SL, Ong MT, Braun PV, Martínez TJ, White SR. J. N. Nature 2009; 459: 68
  • 4 Hsu T.-G, Zhou J, Su H.-W, Schrage BR, Ziegler CJ, Wang J. J. Am. Chem. Soc. 2020; 142: 2100
  • 5 Lin Y, Kouznetsova TB, Craig SL. J. Am. Chem. Soc. 2020; 142: 2105
  • 6 Lin Y, Kouznetsova TB, Chang C.-C, Craig SL. Nat. Commun. 2020; 11: 1
  • 7 Hu X, Zeng T, Husic CC, Robb MJ. J. Am. Chem. Soc. 2019; 141: 15018
  • 8 Huo S, Zhao P, Shi Z, Zou M, Yang X, Warszawik E, Loznik M, Göstl R, Herrmann A. Nat. Chem. 2021; 13: 131
  • 9 Shi Z, Wu J, Song Q, Göstl R, Herrmann A. J. Am. Chem. Soc. 2020; 142: 14725
  • 10 Wang J, Piskun I, Craig SL. ACS Macro Lett. 2015; 4: 834
  • 11 Ramirez AL. B, Kean ZS, Orlicki JA, Champhekar M, Elsakr SM, Krause WE, Craig SL. Nat. Chem. 2013; 5: 757
  • 12 Barbee MH, Wang J, Kouznetsova T, Lu M, Craig SL. Macromolecules 2019; 52: 6234
  • 13 Yang J, Horst M, Romaniuk JA, Jin Z, Cegelski L, Xia Y. J. Am. Chem. Soc. 2019; 141: 6479
  • 14 Kida J, Imato K, Goseki R, Aoki D, Morimoto M, Otsuka H. Nat. Commun. 2018; 9: 1
  • 15 Wang Q, Gossweiler GR, Craig SL, Zhao X. Nat. Commun. 2014; 5: 1
  • 16 Piermattei A, Karthikeyan S, Sijbesma RP. Nat. Chem. 2009; 1: 133
  • 17 Wei K, Gao Z, Liu H, Wu X, Wang F, Xu H. ACS Macro Lett. 2017; 6: 1146
  • 18 Wu S, Wang T, Xu H. ACS Macro Lett. 2020; 9: 1192
  • 19 Katchalsky A, Zwick M. J. Polym. Sci. 1955; 16: 221
  • 20 Staudinger H, Bondy H. Ber. Dtsch. Chem. Ges. B 1930; 3: 519
  • 21 Staudinger H, Leupold E. Ber. Dtsch. Chem. Ges. B 1930; 63: 730
  • 22 Staudinger H, Heuer W. Ber. Dtsch. Chem. Ges. B 1934; 67: 1159
  • 23 Berkowski KL, Potisek SL, Hickenboth CR, Moore JS. Macromolecules 2005; 38: 8975
  • 24 Zhang H, Li X, Lin YJ, Gao F, Tang Z, Su PF, Zhang WK, Xu YZ, Weng WG, Boulatov R. Nat. Commun. 2017; 8: 1147
  • 25 Kato S, Furukawa S, Aoki D, Goseki R, Oikawa K, Tsuchiya K, Shimada N, Maruyama A, Numata K, Otsuka H. Nat. Commun. 2021; 12: 126
  • 26 McFadden ME, Robb MJ. J. Am. Chem. Soc. 2021; 143: 7925
  • 27 Lee DC, Kensy VK, Maroon CR, Long BK, Boydston AJ. Angew. Chem. Int. Ed. 2019; 58: 5639
  • 28 Nixon R, De Bo G. J. Am. Chem. Soc. 2021; 143: 3033
  • 29 Kim TA, Robb MJ, Moore JS, White SR, Sottos NR. Macromolecules 2018; 51: 9177
  • 30 Chen ZX, Zhu XL, Yang JH, Mercer JA. M, Burns NZ, Martinez TJ, Xia Y. Nat. Chem. 2020; 12: 302
  • 31 Robb MJ, Kim TA, Halmes AJ, White SR, Sottos NR, Moore JS. J. Am. Chem. Soc. 2016; 138: 12328
  • 32 Potisek SL, Davis DA, Sottos NR, White SR, Moore JS. J. Am. Chem. Soc. 2007; 129: 13808
  • 33 Qian H, Purwanto NS, Ivanoff DG, Halmes AJ, Sottos NR, Moore JS. Chem 2021; 7: 1080
  • 34 Hu H, Ma ZY, Jia XR. Mater. Chem. Front. 2020; 4: 3115
  • 35 Lavalle P, Boulmedais F, Schaaf P, Jierry L. Langmuir 2016; 32: 7265
  • 36 Li J, Nagamani C, Moore JS. Acc. Chem. Res. 2015; 48: 2181
  • 37 Traeger H, Kiebala DJ, Weder C, Schrettl S. Macromol. Rapid Commun. 2021; 42: 2000573
  • 38 Chen YJ, Mellot G, van Luijk D, Creton C, Sijbesma RP. Chem. Soc. Rev. 2021; 50: 6659
  • 39 Ghanem MA, Basu A, Behrou R, Boechler N, Boydston AJ, Craig SL, Lin YJ, Lynde BE, Nelson A, Shen H, Storti DW. Nat. Rev. Mater. 2021; 6: 84
  • 40 Caruso MM, Davis DA, Shen Q, Odom SA, Sottos NR, White SR, Moore JS. Chem. Rev. 2009; 109: 5755
  • 41 Beyer MK, Clausen-Schaumann H. Chem. Rev. 2005; 105: 2921
  • 42 Wiggins KM, Brantley JN, Bielawski CW. Chem. Soc. Rev. 2013; 42: 7130
  • 43 Stratigaki M, Gostl R. ChemPlusChem 2020; 85: 1095
  • 44 Willis-Fox N, Rognin E, Aljohani TA, Daly R. Chem 2018; 4: 2499
  • 45 Stauch T, Dreuw A. Chem. Rev. 2016; 116: 14137
  • 46 Ribas-Arino J, Marx D. Chem. Rev. 2012; 112: 5412
  • 47 De Bo G. Macromolecules 2020; 53: 7615
  • 48 Huang WM, Wu X, Gao X, Yu YF, Lei H, Zhu ZS, Shi Y, Chen YL, Qin M, Wang W, Cao Y. Nat. Chem. 2019; 11: 310
  • 49 Karman M, Verde-Sesto E, Weder C, Simon YC. ACS Macro Lett. 2018; 7: 1099
  • 50 Lee B, Niu ZB, Wang JP, Slebodnick C, Craig SL. J. Am. Chem. Soc. 2015; 137: 10826
  • 51 Mao YC, Kubota Y, Kurose T, Ishigami A, Seshimo K, Aoki D, Otsuka H, Ito H. Macromolecules 2020; 53: 9313
  • 52 Watabe T, Aoki D, Otsuka H. Macromolecules 2021; 54: 1725
  • 53 Yanada K, Kato S, Aoki D, Mikami K, Sugita H, Otsuka H. Chem. Commun. 2021; 57: 2899
  • 54 Kato S, Aoki D, Otsuka H. ACS Appl. Polym. Mater. 2021; 3: 594
  • 55 Seshimo K, Sakai H, Watabe T, Aoki D, Sugita H, Mikami K, Mao YC, Ishigami A, Nishitsuji S, Kurose T, Ito H, Otsuka H. Angew. Chem. Int. Ed. 2021; 60: 8406
  • 56 Nixon R, De Bo G. Nat. Chem. 2020; 12: 826
  • 57 Karman M, Verde-Sesto E, Weder C. ACS Macro Lett. 2018; 7: 1028
  • 58 Diesendruck CE, Peterson GI, Kulik HJ, Kaitz JA, Mar BD, May PA, White SR, Martinez TJ, Boydston AJ, Moore JS. Nat. Chem. 2014; 6: 624
  • 59 Ayarza J, Wang Z, Wang J, Esser-Kahn AP. ACS Macro Lett. 2021; 10: 799
  • 60 Wagner M, Krieger A, Minameyer M, Hamisch B, Huber K, Drewello T, Grohn F. Macromolecules 2021; 54: 2899
  • 61 Kida J, Aoki D, Otsuka H. ACS Macro Lett. 2021; 10: 558
  • 62 Shi ZY, Wu JN, Song QC, Gostl R, Herrmann A. J. Am. Chem. Soc. 2020; 142: 14725
  • 63 Funtan S, Michael P, Binder WH. Biomimetics 2019; 4: 24
  • 64 Zhang YD, Wang Z, Kouznetsova TB, Sha Y, Xu EH, Shannahan L, Fermen- MCoker, Lin YJ, Tang CB, Craig SL. Nat. Chem. 2021; 13: 56
  • 65 Sha Y, Zhang YD, Xu EH, Wang Z, Zhu TY, Craig SL, Tang CB. ACS Macro Lett. 2018; 7: 1174
  • 66 Di Giannantonio M, Ayer MA, Verde-Sesto E, Lattuada M, Weder C, Fromm KM. Angew. Chem. Int. Ed. 2018; 57: 11445
  • 67 Wei K, Gao ZC, Liu HR, Wu XJ, Wang F, Xu HX. ACS Macro Lett. 2017; 6: 1146
  • 68 Wu HC, Lissel F, Wang GJ. N, Koshy DM, Nikzad S, Yan HP, Xu J, Luo SC, Matsuhisa N, Cheng Y, Wang F, Ji BH, Li DC, Chen WC, Xue G, Bao ZN. Adv. Funct. Mater. 2021; 31: 2009201
  • 69 Telychko M, Su J, Gallardo A, Gu YW, Mendieta-Moreno JL, Qi DC, Tadich A, Song ST, Lyu P, Qiu ZZ, Fang HY, Koh MJ, Wu JS, Jelinek P, Lu J. Angew. Chem. Int. Ed. 2019; 58: 18591
  • 70 Paulusse JM. J, Sijbesma RP. Angew. Chem. Int. Ed. 2004; 43: 4460
  • 71 Razgoniaev AO, Glasstetter LM, Kouznetsova TB, Hall KC, Horst M, Craig SL, Franz KJ. J. Am. Chem. Soc. 2021; 143: 1784
  • 72 Lenhardt JM, Ong MT, Choe R, Evenhuis CR, Martinez TJ, Craig SL. Science 2010; 329: 1057
  • 73 Klukovich HM, Kouznetsova TB, Kean ZS, Lenhardt JM, Craig SL. Nat. Chem. 2013; 5: 110
  • 74 Wang JP, Kouznetsova TB, Niu ZB, Ong MT, Klukovich H, Rheingold AL, Martinez TJ, Craig SL. Nat. Chem. 2015; 7: 323
  • 75 Wang JP, Kouznetsova TB, Boulatov R, Craig SL. Nat. Commun. 2016; 7: 13433
  • 76 Lin YJ, Kouznetsova TB, Craig SL. J. Am. Chem. Soc. 2020; 142: 99
  • 77 Lin YJ, Zhang YD, Wang Z, Craig SL. J. Am. Chem. Soc. 2019; 141: 10943
  • 78 Lenhardt JM, Black AL, Craig SL. J. Am. Chem. Soc. 2009; 131: 10818
  • 79 Wu D, Lenhardt JM, Black AL, Akhremitchev BB. Craig S. L. J. Am. Chem. Soc. 2010; 132: 15936
  • 80 Lenhardt JM, Ogle JW, Ong MT, Choe R, Martinez TJ, Craig SL. J. Am. Chem. Soc. 2011; 133: 3222
  • 81 Wang JP, Kouznetsova TB, Craig SL. J. Am. Chem. Soc. 2015; 137: 11554
  • 82 Kean ZS, Ramirez AL. B, Craig SL. J. Polym. Sci., Part A: Polym. Chem. 2012; 50: 3481
  • 83 Kean ZS, Gossweiler GR, Kouznetsova TB, Hewage GB, Craig SL. Chem. Commun. 2015; 51: 9157
  • 84 Lin YJ, Kouznetsova TB, Chang CC, Craig SL. Nat. Commun. 2020; 11: 4987
  • 85 Bowser BH, Ho CH, Craig SL. Macromolecules 2019; 52: 9032
  • 86 Kryger MJ, Ong MT, Odom SA, Sottos NR, White SR, Martinez TJ, Moore JS. J. Am. Chem. Soc. 2010; 132: 4558
  • 87 Klukovich HM, Kean ZS, Iacono ST, Craig SL. J. Am. Chem. Soc. 2011; 133: 17882
  • 88 Bowser BH, Wang S, Kouznetsova TB, Beech HK, Olsen BD, Rubinstein M, Craig SL. J. Am. Chem. Soc. 2021; 143: 5269
  • 89 Kryger MJ, Munaretto AM, Moore JS. J. Am. Chem. Soc. 2011; 133: 18992
  • 90 Nofen EM, Dasgupta A, Zimmer N, Gunckel R, Koo B, Chattopadhyay A, Dai LL. Polym. Eng. Sci. 2017; 57: 901
  • 91 Yang JH, Horst M, Romaniuk JA. H, Jin ZX, Cegelski L, Xia Y. J. Am. Chem. Soc. 2019; 141: 6479
  • 92 Yang JH, Horst M, Werby SH, Cegelski L, Burns NZ, Xia Y. J. Am. Chem. Soc. 2020; 142: 14619
  • 93 Su JK, Feist JD, Yang JH, Mercer JA. M, Romaniuk JA. H, Chen ZX, Cegelski L, Burns NZ, Xia Y. J. Am. Chem. Soc. 2018; 140: 12388
  • 94 Boswell BR, Mansson CM. F, Cox JM, Jin ZX, Romaniuk JA. H, Lindquist KP, Cegelski L, Xia Y, Lopez SA, Burns NZ. Nat. Chem. 2021; 13: 41
  • 95 Chen ZX, Mercer JA. M, Zhu XL, Romaniuk JA. H, Pfattner R, Cegelski L, Martinez TJ, Burns NZ, Xia Y. Science 2017; 357: 475
  • 96 Wang JP, Kouznetsova TB, Niu ZB, Rheingold AL, Craig SL. J. Org. Chem. 2015; 80: 11895
  • 97 Hickenboth CR, Moore JS, White SR, Sottos NR, Baudry J, Wilson SR. Nature 2007; 446: 423
  • 98 Ribas-Arino J, Shiga M, Marx D. J. Am. Chem. Soc. 2010; 132: 10609
  • 99 Brown CL, Bowser BH, Meisner J, Kouznetsova TB, Seritan S, Martinez TJ, Craig SL. J. Am. Chem. Soc. 2021; 143: 3846
  • 100 Dopieralski P, Anjukandi P, Ruckert M, Shiga M, Ribas-Arino J, Marx D. J. Mater. Chem. 2011; 21: 8309
  • 101 Hu XR, McFadden ME, Barber RW, Robb MJ. J. Am. Chem. Soc. 2018; 140: 14073
  • 102 Jung SM, Yoon HJ. Angew. Chem. Int. Ed. 2021; 60: 23564
  • 103 Klukovich HM, Kean ZS, Ramirez AL. B, Lenhardt JM, Lin JX, Hu XQ, Craig SL. J. Am. Chem. Soc. 2012; 134: 9577
  • 104 Jung S, Kang S, Kuwabara J, Yoon HJ. Polym. Chem. 2019; 10: 4506
  • 105 Kang S, Moon HK, Yoon HJ. Macromolecules 2018; 51: 4068
  • 106 Jung SM, Yoon HJ. Angew. Chem. Int. Ed. 2020; 59: 4883
  • 107 Jung S, Kim SY, Yoon HJ. Synlett 2020; 31: 1343
  • 108 Robb MJ, Moore JS. J. Am. Chem. Soc. 2015; 137: 10946
  • 109 Lin YJ, Chang CC, Craig SL. Org. Chem. Front. 2019; 6: 1052
  • 110 Chen YL, Spiering AJ. H, Karthikeyan S, Peters GW. M, Meijer EW, Sijbesma RP. Nat. Chem. 2012; 4: 559
  • 111 Zhang H, Gao F, Cao XD, Li YQ, Xu YZ, Weng WG, Boulatov R. Angew. Chem. Int. Ed. 2016; 55: 3040
  • 112 Larsen MB, Boydston AJ. J. Am. Chem. Soc. 2013; 135: 8189
  • 113 Larsen MB, Boydston AJ. J. Am. Chem. Soc. 2014; 136: 1276
  • 114 Jakobs RT. M, Ma S, Sijbesma RP. ACS Macro Lett. 2013; 2: 613
  • 115 Stevenson R, De Bo G. J. Am. Chem. Soc. 2017; 139: 16768
  • 116 Gossweiler GR, Hewage GB, Soriano G, Wang QM, Welshofer GW, Zhao XH, Craig SL. ACS Macro Lett. 2014; 3: 216
  • 117 Turksoy A, Yildiz D, Aydonat S, Beduk T, Canyurt M, Baytekin B, Akkaya EU. RSC Adv. 2020; 10: 9182
  • 118 Hsu TG, Zhou JF, Su HW, Schrage BR, Ziegler CJ, Wang JP. J. Am. Chem. Soc. 2020; 142: 2100
  • 119 Yang JH, Xia Y. Chem. Sci. 2021; 12: 4389
  • 120 Tipikin DS. Russ. J. Phys. Chem. 2001; 75: 1720
  • 121 Gossweiler GR, Brown CL, Hewage GB, Sapiro-Gheiler E, Trautman WJ, Welshofer GW, Craig SL. ACS Appl. Mater. Interfaces 2015; 7: 22431
  • 122 Gossweiler GR, Kouznetsova TB, Craig SL. J. Am. Chem. Soc. 2015; 137: 6148
  • 123 Lin YJ, Barbee MH, Chang CC, Craig SL. J. Am. Chem. Soc. 2018; 140: 15969
  • 124 Barbee MH, Kouznetsova T, Barrett SL, Gossweiler GR, Lin YJ, Rastogi SK, Brittain WJ, Craig SL. J. Am. Chem. Soc. 2018; 140: 12746
  • 125 McFadden ME, Robb MJ. J. Am. Chem. Soc. 2019; 141: 11388
  • 126 Klein IM, Husic CC, Kovacs DP, Choquette NJ, Robb MJ. J. Am. Chem. Soc. 2020; 142: 16364