Synthesis of Pillar[6]arenes and Their Host–Guest Complexes

Derong Cao; Herbert Meier

doi:10.1055/s-0034-1378688

Synthesis, Inhaltsverzeichnis

Synthesis 2015; 47(08): 1041-1056
DOI: 10.1055/s-0034-1378688

review

Synthesis of Pillar[6]arenes and Their Host–Guest Complexes

Autor*innen

Derong Cao*

^aSchool of Chemistry and Chemical Engineering, State Key Laboratory of Luminescent Materials and Devices, South China University of Technology, Wushan Road, 510641 Guangzhou, P. R. of China eMail: drcao@scut.edu.cn
Herbert Meier*

^aSchool of Chemistry and Chemical Engineering, State Key Laboratory of Luminescent Materials and Devices, South China University of Technology, Wushan Road, 510641 Guangzhou, P. R. of China eMail: drcao@scut.edu.cn

^bInstitute of Organic Chemistry, University of Mainz, Duesbergweg 10-14, 55099 Mainz, Germany eMail: hmeier@uni-mainz.de

Abstract

Alle Artikel dieser Rubrik

Abstract

Pillar[n]arenes are a fast-growing research topic in supramolecular chemistry. Originally the focus was predominantly on pillar[5]arenes; however, now more and more studies on pillar[6]arenes are being performed. The ability and selectivity of host–guest complexations depend strongly on the size of the inner cavities of these macrocycles. New results have stimulated us to compile the synthetic entries and the complexations of pillar[6]arenes with large cylindric cavities that offer space for many different guest molecules.

1 Introduction

2 Preparation of Pillar[6]arenes

2.1 Pillar[6]arenes by Macrocyclization Reactions

2.2 Hydroxypillar[6]arenes through Ether Cleavage

2.3 Hydroxypillar[6]arenes by Redox Reactions

2.4 Alkylation of Hydroxypillar[6]arenes

2.5 Pillar[6]arenes Obtained from Preformed Pillar[6]arenes by Transformation of Alkoxy Chains

3 Structure of Pillar[6]arenes in the Crystalline State and in Solution

3.1 Dodecaalkoxypillar[6]arenes

3.2 Perhydroxypillar[6]arenes

4 Generation of Complexes

4.1 Inclusion of Guest Molecules

4.2 Complexes of Ammonium Compounds

4.3 Complexes of Pyridinium Compounds

4.4 Complexes of Other Cations

4.5 Complexes of Electroneutral Guest Molecules

4.6 Complexes of Anions

4.7 Self-Assembly by Complexation

4.8 Binding on Metal Surfaces

4.9 Capture of Gases and Vapors

5 Conclusion

Key words

condensation - macrocycles - supramolecular chemistry - host–guest systems - arene complexes

Volltext

Referenzen

References
1 Ogoshi T, Kanai S, Fujinami S, Yamagishi T.-A, Nakamoto Y. J. Am. Chem. Soc. 2008; 130: 5022
2 Cao D, Kou Y, Liang J, Chen Z, Wang L, Meier H. Angew. Chem. Int. Ed. 2009; 48: 9721 ; Angew. Chem. 2009, 121, 9901
3 Ma Y, Zhang Z, Ji X, Han C, He J, Abliz Z, Chen W, Huang F. Eur. J. Org. Chem. 2011; 5331
4 Holler M, Allenbach N, Sonet J, Nierengarten J.-F. Chem. Commun. 2012; 48: 2576
5 Tao H, Cao D, Liu L, Kou Y, Wang L, Meier H. Sci. China Chem. 2012; 55: 223
6 Ogoshi T, Ueshima N, Akutso T, Yamafuji D, Furuta T, Sakakibara F, Yamagishi T.-A. Chem. Commun. 2014; 50: 5774
7 Cragg PJ, Sharma K. Chem. Soc. Rev. 2012; 41: 597
8 Ogoshi T. J. Inclusion Phenom. Macrocyclic Chem. 2011; 72: 247
9 Xue M, Yang Y, Chi X, Zhang Z, Huang F. Acc. Chem. Res. 2012; 45: 1294
10 Ogoshi T, Yamagishi T.-A. Bull. Chem. Soc. Jpn. 2013; 86: 312
11 Ogoshi T, Yamagishi T.-A. Eur. J. Org. Chem. 2013; 2961
12 Zhang HC, Liu ZN, Xin FF, Hao AY. Chin. J. Org. Chem. 2012; 32: 219
13 Zhang H, Zhao Y. Chem. Eur. J. 2013; 19: 16862
14 Cao D, Meier H. Asian J. Org. Chem. 2014; 244; and references therein
15 Strutt NL, Zhang H, Schneebeli ST, Stoddart JF. Acc. Chem. Res. 2014; 47: 2631
16 Hu X.-B, Chen Z, Chen L, Zhang L, Hou J.-L, Li Z.-T. Chem. Commun. 2012; 48: 10999
17 Yang Y, Wang K, Zhang X, Chen D, Song N. Faming Zhuanli Shenqing CN 103396298 A2 0131120, 2013
18 Kou Y, Cao D, Tao H, Wang L, Liang J, Chen Z, Meier H. J. Inclusion Phenom. Macrocyclic Chem. 2013; 77: 279
19 Han C, Ma F, Zhang Z, Xia B, Yu Y, Huang F. Org. Lett. 2010; 12: 4360
20 Nierengarten I, Guerra S, Holler M, Karmazin-Brelot L, Barberá J, Deschenaux R, Nierengarten J.-F. Eur. J. Org. Chem. 2013; 3675
21 Yao Y, Li J, Dai J, Chi X, Xue M. RSC Adv. 2014; 4: 9039
22 Chen W, Zhang Y, Li J, Lou X, Yu Y, Jia X, Li C. Chem. Commun. 2013; 49: 7956
23 Ma Y, Jang J, Li J, Chi X, Xue M. RSC Adv. 2013; 3: 23953
24 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
25 Ogoshi T, Demachi K, Masaki K, Yamagishi T.-A. Chem. Commun. 2013; 49: 3952
26 Ogoshi T, Ueshima N, Sakakibara F, Yamagishi T.-A, Haino T. Org. Lett. 2014; 16: 2896
27 Ma Y, Chi X, Yan X, Liu J, Yao Y, Chen W, Huang F, Hou J.-L. Org. Lett. 2012; 14: 1532
28 Ogoshi T, Kayama H, Yamafuji D, Aoki T, Yamagishi T.-A. Chem. Sci. 2012; 3: 3221
29 Xia W, Hu X.-Y, Chen Y, Lin C, Wang L. Chem. Commun. 2013; 49: 5085
30 Ogoshi T, Yamafuji D, Kotera D, Aoki T, Fujinami S, Yamagishi T.-A. J. Org. Chem. 2012; 77: 11146
31 Han C, Gao L, Yu G, Zhang Z, Dong S, Huang F. Eur. J. Org. Chem. 2013; 2529
32 Yu G, Tang G, Huang F. J. Mater. Chem. C 2014; 2: 6609
33 Lao K.-U, Yu C.-H. J. Comput. Chem. 2011; 32: 2716
34 Chi X, Xue M, Ma Y, Yan X, Huang F. Chem. Commun. 2013; 49: 8175
35 Ogoshi T, Kida K, Yamagishi T.-A. J. Am. Chem. Soc. 2012; 134: 20146
36 Yu G, Xue M, Zhang Z, Li J, Han C, Huang F. J. Am. Chem. Soc. 2012; 134: 13248
37 Chen L, Si W, Zhang L, Tang G, Li Z.-T, Hou J.-L. J. Am. Chem. Soc. 2013; 135: 2152
38 Yu G, Han C, Zhang Z, Chen J, Yan X, Zheng B, Liu S, Huang F. J. Am. Chem. Soc. 2012; 134: 8711
39 Barnes JC, Paton JD, Damewood JR. Jr, Mislow K. J. Org. Chem. 1981; 46: 4975
40 Ogoshi T, Masaki K, Shiga R, Kitajima K, Yamagishi T.-A. Org. Lett. 2011; 13: 1264
41 Peerannawar SR, Gejji SP. Phys. Chem. Chem. Phys. 2012; 14: 8711
42 Gejji SP. personal communication
43 Han C, Zhang Z, Chi X, Zhang M, Yu G, Huang F. Acta Chim. Sin. (Engl. Ed.) 2012; 70: 1775
44 Adnikari BB, Fujii A, Schramm MP. Eur. J. Org. Chem. 2014; 2972
45 Xia D, Yu G, Li J, Huang F. Chem. Commun. 2014; 50: 3606
46 Wang P, Yan X, Huang F. Chem. Commun. 2014; 50: 5017
47 Zhou Q, Jiang H, Chen R, Qiu F, Dai G, Han D. Chem. Commun. 2014; 50: 10658
48 Li C, Shu X, Li J, Fan J, Chen Z, Wenig L, Jia X. Org. Lett. 2012; 14: 4126
49 Yang J, Yu G, Xia D, Huang F. Chem. Commun. 2014; 50: 3993
50 Ogoshi T, Yamafuji D, Aoki T, Yamagishi T.-A. Chem. Commun. 2012; 48: 6842

51a Cao Y, Hu X.-Y, Li Y, Zou X, Xiong S, Lin C, Shen Y.-Z, Wang L. J. Am. Chem. Soc. 2014; 136: 10762

See also:

51b Cao Y, Li Y, Hu X.-Y, Zou X, Xiong S, Lin C, Wang L. Chem. Mater. 2015; 27: 1110

52 Hou X, Ke C, Cheng C, Song N, Blackburn AK, Sarjeant AA, Botros YY, Yang Y.-W, Stoddart JF. Chem. Commun. 2014; 50: 6196
53 Yu G, Zhou X, Zhang Z, Han C, Mao Z, Gao C, Huang F. J. Am. Chem. Soc. 2012; 134: 19489
54 See also: Ge Z, Liu S. Chem. Soc. Rev. 2013; 42: 7289
55 Ji X, Chen J, Chi X, Huang F. ACS Macro Lett. 2014; 3: 110
56 Huang X, Du X. ACS Appl. Mater. Interfaces 2014; 6: 20430
57 Fan J, Deng H, Li J, Jia X, Li C. Chem. Commun. 2013; 49: 6343
58 Duan Q, Cao Y, Li Y, Hu X, Xiao T, Lin C, Pan Y, Wang L. J. Am. Chem. Soc. 2013; 135: 10542
59 Zhou J, Chen M, Diao G. Chem. Commun. 2014; 50: 11954
60 Yao Y, Jie K, Zhou Y, Xue M. Tetrahedron Lett. 2014; 55: 3195
61 Yao Y, Jie K, Zhou Y, Xue M. Chem. Commun. 2014; 50: 5072
62 Ogoshi T, Sueto R, Yoshikoshi K, Yamagishi T.-A. Chem. Commun. 2014; 50: 15209
63 Liu L, Cao D, Jin Y, Tao H, Kou Y, Meier H. Org. Biomol. Chem. 2011; 9: 7007
64 Gribble GW, Nutaitis CF. Tetrahedron Lett. 1985; 26: 6023
65 Yang T.-F, Chiu KY, Cheng H.-C, Lee JW, Kuo MY, Su YO. J. Org. Chem. 2012; 77: 8627
66 Ito A, Yokoyama Y, Aihara R, Fukui K, Eguchi S, Shizu K, Sato T, Tanaka K. Angew. Chem. Int. Ed. 2010; 49: 8205 ; Angew. Chem. 2010, 122, 8381
67 See also: Ide T, Takeuchi D, Osaka K, Sato T, Higuchi M. J. Org. Chem. 2011; 76: 9504
68 Takeuchi D, Asano I, Osakada K. J. Org. Chem. 2006; 71: 8614
69 Schneebeli ST, Cheng C, Hartlieb KJ, Strutt NL, Sarjeant AA, Stern CL, Stoddart JF. Chem. Eur. J. 2013; 19: 3860