A General Approach for Synthesis of Circularly Assembled Supramolecular Polymers by Means of Region-confined Amphiphilic Supramolecular Polymerization

Abstract

Topological supramolecular polymers are responsible for design of innovative materials with unique physical properties but remain a challenging task to prepare by means of supramolecular polymerization. In this contribution, we present a novel method of region-confined amphiphilic supramolecular polymerization (RASP) in a controllable two-step self-organization pathway, which was certified by a new type of pyridine-oxadiazole alternating 48-membered macrocycles with structurally regional distribution of distinct self-assembling groups that can self-organize into circular supramolecular architectures. Meanwhile, water molecule plays a crucial role in RASP, and the water content in nonpolar solvent chloroform is sensitive to trigger controllable amphiphilic self-organization. Moreover, differing from the traditional rodlike micelles formed by self-assembly of linearly amphiphilic molecules, this approach of RASP exclusively gives rise to the formation of circularly assembled supramolecular polymers.

Keywords

Supramolecular polymerization / Circular supramolecular architecture / Controllable self-assembly / Organic macrocycle / Region-confined amphiphilic supramolecular polymerization

References

[1] Yang L, Tan X, Wang Z, Zhang X. Chem. Rev., 2015, 115: 7196.

[2] Clemons T D, Stupp S I. Prog. Polym. Sci., 2020, 111: 101310.

[3] Guo D S, Liu Y. Chem. Soc. Rev., 2012, 41: 5907.

[4] Hashim P K, Bergueiro J, Meijer E W, Aida T. Prog. Polym. Sci., 2020, 105: 101250.

[5] Qin B, Yin Z, Tang X, Zhang S, Wu Y, Xu J-F, Zhang X. Prog. Polym. Sci., 2020, 100: 101167.

[6] Yagai S, Kitamoto Y, Datta S, Adhikari B. Acc. Chem. Res., 2019, 52: 1325.

[7] Fenniri H, Packiarajan M, Vidale K L, Sherman D M, Hallenga K, Wood K V, Stowell J G. J. Am. Chem. Soc., 2001, 123: 3854.

[8] Percec V, Dulcey A E, Balagurusamy V S K, Miura Y, Smidrkal J, Peterca M, Nummelin S, Edlund U, Hudson S D, Heiney P A, Duan H, Magonov S N, Vinogradov S A. Nature, 2004, 430: 764.

[9] Shimizu T, Masuda M, Minamikawa H. Chem. Rev., 2005, 105: 1401.

[10] Huang Z, Kang S K, Banno M, Yamaguchi T, Lee D, Seok C, Yashima E, Lee M. Science, 2012, 337: 1521.

[11] Fukino T, Joo H, Hisada Y, Obana M, Yamagishi H, Hikima T, Takata M, Fujita N, Aida T. Science, 2014, 344: 499.

[12] Beingessner R L, Fan Y, Fenniri H. RSC Adv., 201, 6: 75820.

[13] Yashima E, Ousaka N, Taura D, Shimomura K, Ikai T, Maeda K. Chem. Rev., 201, 116: 13752.

[14] Ghadiri M R, Granja J R, Milligan R A, Mcree D E, Khazanovich N. Nature, 1993, 366: 324.

[15] Kim Y, Kang J, Shen B, Wang Y, He Y, Lee M. Nat. Commun., 2015, 6: 8650.

[16] Hirschberg J H K K, Brunsveld L, Ramzi A, Vekemans J A J M, Sijbesma R P, Meijer E W. Nature, 2000, 407: 167.

[17] Zhang C, Deng X, Wang C, Bao C, Yang B, Zhang H, Qi S, Dong Z. Chem. Sci., 2019, 10: 8648.

[18] Suzuki A, Aratsu K, Datta S, Shimizu N, Takagi H, Haruki R, Adachi S I, Hollamby M, Silly F, Yagai S. J. Am. Chem. Soc., 2019, 141: 13196.

[19] Kim J K, Lee E, Huang Z G, Lee M. J. Am. Chem. Soc., 200, 128: 14022.

[20] Shen B, Zhu Y, Kim Y, Zhou X, Sun H, Lu Z, Lee M. Nat. Commun., 2019, 10: 1080.

[21] Datta S, Kato Y, Higashiharaguchi S, Aratsu K, Isobe A, Saito T, Prabhu D D, Kitamoto Y, Hollamby M J, Smith A J, Dalgliesh R, Mahmoudi N, Pesce L, Perego C, Pavan G M, Yagai S. Nature, 2020, 583: 400.

[22] De Greef T F, Smulders M M, Wolffs M, Schenning A P, Sijbesma R P, Meijer E W. Chem. Rev., 2009, 109: 5687.

[23] Korevaar P A, George S J, Markvoort A J, Smulders M M, Hilbers P A, Schenning A P, De Greef T F, Meijer E W. Nature, 2012, 481: 492.

[24] Ghadiri M R, Granja J R, Buehler L K. Nature, 1994, 369: 301.

[25] Kim Y, Li H, He Y, Chen X, Ma X, Lee M. Nat. Nanotechnol., 2017, 12: 551.

[26] Zhang K, Zha Y, Peng B, Chen Y, Tew G N. J. Am. Chem. Soc., 2013, 135: 15994.

[27] Zhu J, Dong Z, Lei S, Cao L, Yang B, Li W, Zhang Y, Liu J, Shen J. Angew. Chem. Int. Ed., 2015, 54: 3097.

[28] Van Zee N J, Adelizzi B, Mabesoone M F J, Meng X, Aloi A, Zha R H, Lutz M, Filot I A W, Palmans A R A, Meijer E W. Nature, 2018, 558: 100.

[29] Ogasawara M, Lin X, Kurata H, Ouchi H, Yamauchi M, Ohba T, Kajitani T, Fukushima T, Numata M, Nogami R, Adhikari B, Yagai S. Mater. Chem. Front., 2018, 2: 171.