Copillar[5]arene Chemistry: Synthesis and Applications

Wenzhang Chen; Stéphane P. Vincent

doi:10.1055/s-0040-1738369

Synthesis, Table of Contents

Synthesis 2023; 55(02): 246-262
DOI: 10.1055/s-0040-1738369

short review

Special Issue dedicated to Prof. Alain Krief

Copillar[5]arene Chemistry: Synthesis and Applications

Wenzhang Chen

^aGuizhou Provincial Engineering Technology Research Center for Chemical Drug R&D, Guizhou Medical University, Guiyang, 550004, P. R. of China

^bDepartment of Chemistry, UNamur, NARILIS, Rue de Bruxelles 61, B-5000 Namur, Belgium

,

Stéphane P. Vincent∗

^bDepartment of Chemistry, UNamur, NARILIS, Rue de Bruxelles 61, B-5000 Namur, Belgium

› Author Affiliations

Abstract

All articles of this category

Abstract

Research on pillar[n]arenes has witnessed a very quick expansion. This emerging class of functionalized macrocyclic oligoarenes not only offers host–guest properties due to the presence of the central cavity, but also presents a wide variety of covalent functionalization possibilities. This short review focuses on copillararenes, a subfamily of pillar[n]arenes. In copillararenes, at least one of the hydroquinone units bears different functional groups compared to the others. After having defined the particular features of copillararenes, this short review compares the different synthetic strategies allowing their construction. Some key applications and future perspectives are also described.

1 Introduction

2 General Features of Pillar[5]arenes

3 Synthesis of Functionalized Copillar[4+1]arenes

4 Concluding Remarks

Key words

copillararenes - supramolecular chemistry - macrocycles - host–guest compounds - phenols

Full Text

References

References
1 Liu Z, Nalluri SK. M, Stoddart JF. Chem. Soc. Rev. 2017; 46: 2459
2 Forgan RS, Sauvage J.-P, Stoddart JF. Chem. Rev. 2011; 111: 5434
3 Ikeda A, Shinkai S. Chem. Rev. 1997; 97: 1713
4 Odell B, Reddington MV, Slawin AM, Spencer N, Stoddart JF, Williams D. Angew. Chem. Int. Ed. 1988; 27: 1547
5 Murray J, Kim K, Ogoshi T, Yao W, Gibb BC. Chem. Soc. Rev. 2017; 46: 2479
6 Rekharsky MV, Inoue Y. Chem. Rev. 1998; 98: 1875
7 Pedersen C. J. Am. Chem. Soc. 1967; 89: 7017
8 Lee JW, Samal S, Selvapalam N, Kim HJ, Kim K. Acc. Chem. Res. 2003; 36: 621
9 Perret F, Lazar AN, Coleman AW. Chem. Commun. 2006; 2425
10 Ogoshi T. Monographs in Supramolecular Chemistry No. 18: Pillararenes. Royal Society of Chemistry; Cambridge: 2015
11 Yu G, Han C, Zhang Z, Chen J, Yan X, Zheng B, Liu S, Huang F. J. Am. Chem. Soc. 2012; 134: 8711
12 Chi X, Ji X, Xia D, Huang F. J. Am. Chem. Soc. 2015; 137: 1440
13 Yu G, Xue M, Zhang Z, Li J, Han C, Huang F. J. Am. Chem. Soc. 2012; 134: 13248
14 Chi X, Yu G, Shao L, Chen J, Huang F. J. Am. Chem. Soc. 2016; 138: 3168
15 Jie K, Zhou Y, Li E, Zhao R, Liu M, Huang F. J. Am. Chem. Soc. 2018; 140: 3190
16 Jie K, Zhou Y, Li E, Huang F. Acc. Chem. Res. 2018; 51: 2064
17 Jie K, Zhou Y, Li E, Zhao R, Huang F. Angew. Chem. Int. Ed. 2018; 57: 12845
18 Li E, Jie K, Zhou Y, Zhao R, Huang F. J. Am. Chem. Soc. 2018; 140: 15070
19 Li E, Zhou Y, Zhao R, Jie K, Huang F. Angew. Chem. Int. Ed. 2019; 58: 3981
20 Yu G, Ma Y, Han C, Yao Y, Tang G, Mao Z, Gao C, Huang F. J. Am. Chem. Soc. 2013; 135: 10310
21 Demay-Drouhard P, Du K, Samanta K, Wan X, Yang W, Srinivasan R, Sue AC.-H, Zuilhof H. Org. Lett. 2019; 21: 3976
22 Wu L, Han C, Jing X, Yao Y. Chin. Chem. Lett. 2021; 32: 3322
23 Zhang Z, Xia B, Han C, Yu Y, Huang F. Org. Lett. 2010; 12: 3285
24 Vincent SP, Buffet K, Nierengarten I, Imberty A, Nierengarten JF. Chem. Eur. J. 2016; 22: 88
25 Ogoshi T, Yamagishi T.-a, Nakamoto Y. Chem. Rev. 2016; 116: 7937
26 Ogoshi T. J. Incl. Phenom. Macrocycl. Chem. 2012; 72: 247
27 Song N, Kakuta T, Yamagishi TA, Yang Y.-W, Ogoshi T. Chem 2018; 4: 2029
28 Li H, Quan K, Yang X, Li Z, Zhao L, Qiu H. Trends Anal. Chem. 2020; 131: 116026
29 Ogoshi T, Kanai S, Fujinami S, Yamagishi T.-a, Nakamoto Y. J. Am. Chem. Soc. 2008; 130: 5022
30 Ogoshi T, Yamagishi T. Chem Commun. 2014; 50: 4776
31 Morohashi N, Narumi F, Iki N, Hattori T, Miyano S. Chem. Rev. 2006; 106: 5291
32 Cragg PJ, Sharma K. Chem. Soc. Rev. 2012; 41: 597
33 Du K, Demay-Drouhard P, Samanta K, Li S, Thikekar TU, Wang H, Guo M, Van Lagen B, Zuilhof H, Sue AC.-H. J. Org. Chem. 2020; 85: 11368
34 Sathiyajith C, Shaikh RR, Han Q, Zhang Y, Meguellati K, Yang Y.-W. Chem. Commun. 2017; 53: 677
35 Xue M, Yang Y, Chi X, Zhang Z, Huang F. Acc. Chem. Res. 2012; 45: 1294
36 Ogoshi T, Aoki T, Kitajima K, Fujinami S, Yamagishi T.-a, Nakamoto Y. J. Org. Chem. 2011; 76: 328
37 Wang Y, Ping G, Li C. Chem Commun. 2016; 52: 9858
38 Ogoshi T, Kakuta T, Yamagishi T. a. Angew. Chem. Int. Ed. 2019; 58: 2197
39 Ogoshi T, Kitajima K, Yamagishi T.-a, Nakamoto Y. Org. Lett. 2010; 12: 636
40 Chen JF, Yin X, Wang B, Zhang K, Meng G, Zhang S, Shi Y, Wang N, Wang S, Chen P. Angew. Chem. Int. Ed. 2020; 132: 11363
41 Park J, Choi Y, Lee SS, Jung JH. Org. Lett. 2019; 21: 1232
42 Ogoshi T, Kitajima K, Aoki T, Yamagishi T.-a, Nakamoto Y. J. Phys. Chem. Lett. 2010; 1: 817
43 Strutt NL, Fairen-Jimenez D, Iehl J, Lalonde MB, Snurr RQ, Farha OK, Hupp JT, Stoddart JF. J. Am. Chem. Soc. 2012; 134: 17436
44 Peerannawar SR, Gejji SP. Comput. Theor. Chem. 2012; 999: 169
45 Ogoshi T, Yamafuji D, Aoki T, Kitajima K, Yamagishi T. a, Hayashi Y, Kawauchi S. Chem. Eur. J. 2012; 18: 7493
46 Kitajima K, Ogoshi T, Yamagishi T.-a. Chem Commun. 2014; 50: 2925
47 Strutt NL, Forgan RS, Spruell JM, Botros YY, Stoddart JF. J. Am. Chem. Soc. 2011; 133: 5668
48 Ogoshi T, Masaki K, Shiga R, Kitajima K, Yamagishi T.-a. Org. Lett. 2011; 13: 1264
49 Ogoshi T, Yamafuji D, Akutsu T, Naito M, Yamagishi T.-a. Chem Commun. 2013; 49: 8782
50 Li G, Fan C, Cheng G, Wu W, Yang C. J. Org. Chem. 2019; 15: 1601
51 Barboiu M. Angew. Chem. Int. Ed. 2012; 51: 11674
52 Si W, Chen L, Hu XB, Tang G, Chen Z, Hou JL, Li ZT. Angew. Chem. Int. Ed. 2011; 50: 12564
53 Wang R, Sun Y, Zhang F, Song M, Tian D, Li H. Angew. Chem. Int. Ed. 2017; 56: 5294
54 Li Q, Li X, Ning L, Tan CH, Mu Y, Wang R. Small 2019; 15: e1804678
55 Liu D, Du J, Qi S, Li M, Wang J, Liu M, Du X, Wang X, Ren B, Wu D. Mater. Chem. Front. 2021; 5: 1418
56 Feng W, Jin M, Yang K, Pei Y, Pei Z. Chem. Commun. 2018; 54: 13626
57 Xiao T, Qi L, Zhong W, Lin C, Wang R, Wang L. Mater. Chem. Front. 2019; 3: 1973
58 Joseph R, Naugolny A, Feldman M, Herzog IM, Fridman M, Cohen Y. J. Am. Chem. Soc. 2016; 138: 754
59 Yu G, Tang G, Huang F. J. Mater. Chem. C 2014; 2: 6609
60 Yu G, Wu D, Li Y, Zhang Z, Shao L, Zhou J, Hu Q, Tang G, Huang F. Chem. Sci. 2016; 7: 3017
61 Chen J.-Y, Li X.-Y, Wu J, Wu Y, Kuang G.-C. Tetrahedron 2020; 76: 131698
62 Cen M, Ding Y, Wang J, Yuan X, Lu B, Wang Y, Yao Y. ACS Macro Lett. 2020; 9: 1558
63 Zhou J, Hua B, Shao L, Feng H, Yu G. Chem. Commun. 2016; 52: 5749
64 Galanos N, Gillon E, Imberty A, Matthews SE, Vidal S. Org. Biomol. Chem. 2016; 14: 3476
65 Yang Q.-Y, Zhang Y.-M, Ma X.-Q, Dong H.-Q, Zhang Y.-F, Guan W.-L, Yao H, Wei T.-B, Lin Q. Spectrochim. Acta, Part A 2020; 240: 118569
66 Chen J.-F, Lin Q, Yao H, Zhang Y.-M, Wei T.-B. Mater. Chem. Front. 2018; 2: 999
67 Liu J, Fan Y.-Q, Song S.-S, Gong G.-F, Wang J, Guan X.-W, Yao H, Zhang Y.-M, Wei T.-B, Lin Q. ACS Sustainable Chem. Eng. 2019; 7: 11999
68 Tian M.-m, Chen D.-X, Sun Y.-L, Yang Y.-W, Jia Q. RSC Adv. 2013; 3: 22111
69 Bernardi A, Jiménez-Barbero J, Casnati A, De Castro C, Darbre T, Fieschi F, Finne J, Funken H, Jaeger K.-E, Lahmann M. Chem. Soc. Rev. 2013; 42: 4709
70 Ehrlich PH. J. Theor. Biol. 1979; 81: 123
71 García Moreno MI, Ortega Caballero F, Rísquez Cuadro R, García Fernández JM, Ortiz Mellet C. Chem. Eur. J. 2017; 23: 6295
72 Nierengarten I, Buffet K, Holler M, Vincent SP, Nierengarten J.-F. Tetrahedron Lett. 2013; 54: 2398
73 Buffet K, Nierengarten I, Galanos N, Gillon E, Holler M, Imberty A, Matthews SE, Vidal S, Vincent SP, Nierengarten JF. Chem. Eur. J. 2016; 22: 2955
74 Guo M, Wang X, Zhan C, Demay-Drouhard P, Li W, Du K, Olson MA, Zuilhof H, Sue AC.-H. J. Am. Chem. Soc. 2018; 140: 74
75 Zhang Z, Luo Y, Xia B, Han C, Yu Y, Chen X, Huang F. Chem. Commun. 2011; 47: 2417
76 Du K, Sue AC.-H. Synlett 2019; 30: 2209
77 Zhao J, Yang W, Liang C, Gao L, Xu J, Sue AC.-H, Zhao H. Chem Commun. 2021; 57: 11193
78 Wei P, Yan X, Li J, Ma Y, Yao Y, Huang F. Tetrahedron 2012; 68: 9179
79 Ogoshi T, Kitajima K, Fujinami S, Yamagishi TA. Chem. Commun. 2011; 47: 10106
80 Ogoshi T, Demachi K, Kitajima K, Yamagishi TA. Chem. Commun. 2011; 47: 7164
81 Chen Y, He M, Li B, Wang L, Meier H, Cao D. RSC Adv. 2013; 3: 21405
82 Han J, Hou X, Ke C, Zhang H, Strutt NL, Stern CL, Stoddart JF. Org. Lett. 2015; 17: 3260
83 Ogoshi T, Yamafuji D, Kotera D, Aoki T, Fujinami S, Yamagishi TA. J. Org. Chem. 2012; 77: 11146
84 Han C, Zhang Z, Yu G, Huang F. Chem. Commun. 2012; 48: 9876
85 Pan M, Xue M. Eur. J. Org. Chem. 2013; 4787
86 Pan M, Xue M. RSC Adv. 2013; 3: 20287
87 Pan M, Xue M. RSC Adv. 2014; 4: 260
88 Liu L, Cao D, Jin Y, Tao H, Kou Y, Meier H. Org. Biomol. Chem. 2011; 9: 7007
89 Wang K, Tan L.-L, Chen D.-X, Song N, Xi G, Zhang SX.-A, Li C, Yang Y.-W. Org. Biomol. Chem. 2012; 10: 9405
90 Zhang Z, Luo Y, Chen J, Dong S, Yu Y, Ma Z, Huang F. Angew. Chem. Int. Ed. 2011; 50: 1397
91 Roy SG, Mondal S, Ghosh K. New J. Chem. 2020; 44: 5921
92 Li R, Jia Q, Du X, Deng R, Wang M, Wang C, Meguellati K. Asian J. Org. Chem. 2020; 9: 549
93 Al-Azemi TF, Mohamod AA, Vinodh M, Alipour FH. Org. Chem. Front. 2018; 5: 10
94 Mao W, Zhan S, Zhu B, Ma D. J. Org. Chem. 2018; 83: 4147
95 Wang X, Han K, Li J, Jia X, Li C. Polym. Chem. 2013; 4: 3998
96 Wang X, Deng H, Li J, Zheng K, Jia X, Li C. Macromol. Rapid Commun. 2013; 34: 1856
97 Li H, Zhu Y, Shi B, Wu G, Zhang Y, Lin Q, Yao H, Wei T. Chin. J. Chem. 2015; 33: 373
98 Chen J.-F, Cheng X.-B, Li H, Lin Q, Yao H, Zhang Y.-M, Wei T.-B. New J. Chem. 2017; 41: 2148
99 Xie C, Hu W, Hu W, Liu YA, Huo J, Li J, Jiang B, Wen K. Chin. J. Chem. 2015; 33: 379
100 Wei P, Li D, Shi B, Wang Q, Huang F. Chem. Commun. 2015; 51: 15169
101 Ogoshi T, Yoshikoshi K, Aoki T, Yamagishi TA. Chem. Commun. 2013; 49: 8785
102 Kothur RR, Fucassi F, Dichello G, Doudet L, Abdalaziz W, Patel BA, Cave GW, Gass IA, Sarker DK, Mikhalovsky S. Supramol. Chem. 2016; 28: 436
103 Zhang H, Strutt NL, Stoll RS, Li H, Zhu Z, Stoddart JF. Chem. Commun. 2011; 47: 11420
104 Strutt NL, Zhang H, Giesener MA, Lei J, Stoddart JF. Chem. Commun. 2012; 48: 1647
105 Zhang H, Ma X, Guo J, Nguyen KT, Zhang Q, Wang X.-J, Yan H, Zhu L, Zhao Y. RSC Adv. 2013; 3: 368
106 Jia Q, Du X, Wang C, Meguellati K. Chin. Chem. Lett. 2019; 30: 721
107 Yu G, Hua B, Han C. Org. Lett. 2014; 16: 2486
108 Blanco JL. J, Mellet CO, Fernández JM. G. Chem. Soc. Rev. 2013; 42: 4518
109 Ponader D, Maffre P, Aretz J, Pussak D, Ninnemann NM, Schmidt S, Seeberger PH, Rademacher C, Nienhaus GU, Hartmann L. J. Am. Chem. Soc. 2014; 136: 2008
110 Muller C, Despras G, Lindhorst TK. Chem. Soc. Rev. 2016; 45: 3275
111 Choi H.-K, Lee D, Singla A, Kwon JS.-I, Wu H.-J. Glycobiology 2019; 29: 397
112 Chen W, Mohy Ei Dine T, Vincent SP. Chem. Commun. 2021; 57: 492
113 Bi J, Zeng X, Tian D, Li H. Org. Lett. 2016; 18: 1092
114 Nierengarten I, Guerra S, Holler M, Nierengarten J.-F, Deschenaux R. Chem. Commun. 2012; 48: 8072
115 Kalograiaki I, Abellán-Flos M, Fernández L. Á, Menendez M, Vincent SP, Solís D. Anal. Chem. 2018; 90: 12314
116 Timmer BJ, Flos MA, Jørgensen LM, Proverbio D, Altun S, Ramström O, Aastrup T, Vincent S. Chem. Commun. 2016; 52: 12326
117 Munoz A, Sigwalt D, Illescas BM, Luczkowiak J, Rodriguez-Perez L, Nierengarten I, Holler M, Remy JS, Buffet K, Vincent SP, Rojo J, Delgado R, Nierengarten JF, Martin N. Nat. Chem. 2016; 8: 50
118 Beaussart A, Abellan-Flos M, El-Kirat-Chatel S, Vincent SP, Dufrene YF. Nano Lett. 2016; 16: 1299
119 Durka M, Buffet K, Iehl J, Holler M, Nierengarten J.-F, Taganna J, Bouckaert J, Vincent SP. Chem. Commun. 2011; 47: 1321
120 Durka M, Buffet K, Iehl J, Holler M, Nierengarten J.-F, Vincent SP. Chem. Eur. J. 2012; 18: 641
121 Poncin K, Roba A, Jimmidi R, Potemberg G, Fioravanti A, Francis N, Willemart K, Zeippen N, Machelart A, Biondi EG, Muraille E, Vincent SP, De Bolle X. Nat. Commun. 2019; 10: 4847
122 Sletten EM, Bertozzi CR. Acc. Chem. Res. 2011; 44: 666
123 Moh El Dine T, Jimmidi R, Diaconu A, Fransolet M, Michiels C, Winter JD, Gillon E, Imberty A, Coenye T, Vincent SP. J. Med. Chem. 2021; 64: 14728
124 Tikad A, Fu H, Sevrain CM, Laurent S, Nierengarten JF, Vincent SP. Chem. Eur. J. 2016; 22: 13147
125 Buffet K, Gillon E, Holler M, Nierengarten J.-F, Imberty A, Vincent SP. Org. Biomol. Chem. 2015; 13: 6482
126 Abellán-Flos M, Tanç M, Supuran CT, Vincent SP. Org. Biomol. Chem. 2015; 13: 7445