Recent Developments and Applications of Chiral Tetraphenylenes

Jian-Wei Han; Jing-Xing Chen; Xin Li; Xiao-Shui Peng; Henry N. C. Wong

doi:10.1055/s-0033-1339859

Synlett, Table of Contents

Synlett 2013; 24(17): 2188-2198
DOI: 10.1055/s-0033-1339859

account

Recent Developments and Applications of Chiral Tetraphenylenes

Authors

Jian-Wei Han*

^aShanghai–Hong Kong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry, The Chinese Academy of Sciences, 345 Ling Ling Road, Shanghai 200032, P. R. of China
Jing-Xing Chen

^aShanghai–Hong Kong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry, The Chinese Academy of Sciences, 345 Ling Ling Road, Shanghai 200032, P. R. of China
Xin Li

^aShanghai–Hong Kong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry, The Chinese Academy of Sciences, 345 Ling Ling Road, Shanghai 200032, P. R. of China
Xiao-Shui Peng

^bDepartment of Chemistry, Center of Novel Functional Molecules, Institute of Molecular Functional Materials and State Key Laboratory of Synthetic Chemistry, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong SAR, P. R. of China Fax: +86(21)54925383 Email: hncwong@cuhk.edu.hk
Henry N. C. Wong*

^aShanghai–Hong Kong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry, The Chinese Academy of Sciences, 345 Ling Ling Road, Shanghai 200032, P. R. of China

^bDepartment of Chemistry, Center of Novel Functional Molecules, Institute of Molecular Functional Materials and State Key Laboratory of Synthetic Chemistry, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong SAR, P. R. of China Fax: +86(21)54925383 Email: hncwong@cuhk.edu.hk

Abstract

All articles of this category

Abstract

Developments of tetraphenylene chemistry in our laboratories (Shanghai and Hong Kong) since 2009 are summarized. The properties and new applications of the structurally unique tetraphenylene derivatives are described in the context of helical macrocycles, asymmetric catalysis, host–guest chemistry, and liquid crystalline molecules. Some future challenges in this field are also presented.

1 Introduction

2 Structure and Properties of Tetraphenylenes

3 Tetraphenylenes and Helical Macrocycles

4 Tetraphenylenes and Asymmetric Catalysis

5 Tetraphenylenes and Host–Guest Chemistry

6 Tetraphenylenes and Liquid Crystalline Molecules

7 Conclusion and Perspectives

Key words

tetraphenylene - asymmetric catalysis - helical structures - host–guest systems - liquid crystalline compounds

Full Text

References

References
1 Sondheimer F. Acc. Chem. Res. 1972; 5: 81 ; and references cited therein

2a Willstätter R, Waser E. Ber. Dtsch. Chem. Ges. 1911; 44: 3423
2b Willstätter R, Heidelberger M. Ber. Dtsch. Chem. Ges. 1913; 46: 517

3a Hückel E. Z. Phys. 1931; 70: 204
3b Hückel E. Z. Elektrochem. 1937; 43: 752
3c Hückel E. Grundzüge der Theorie ungesättigter und aromatischer Verbindungen. Verlag Chemie; Berlin: 1938

4a Salem L In The Molecular Orbital Theory of Conjugated Systems. Benjamin; New York: 1966: 486-491
4b Englman R. The Jahn–Teller Effect in Molecules and Crystals . Wiley-Interscience; London: 1966: 243-245

5a Reppe W, Schlichting O, Klager K, Toepel T. Justus Liebigs Ann. Chem. 1948; 560: 1
5b Katz TJ. J. Am. Chem. Soc. 1960; 82: 3784
5c Katz TJ. J. Am. Chem. Soc. 1960; 82: 3785

6 Dürr H, Klauck G, Peters K, von Schnering HG. Angew. Chem. Int. Ed. Engl. 1983; 22: 332

7a Huang NZ, Sondheimer F. Acc. Chem. Res. 1982; 15: 96
7b Wong HN. C. Acc. Chem. Res. 1989; 22: 145

8a Wong HN. C, Sondheimer F. Angew. Chem. Int. Ed. Engl. 1976; 15: 117
8b Wong HN. C, Chan T.-L, Sondheimer F. Tetrahedron Lett. 1978; 19: 667
8c Wong HN. C, Sondheimer F. J. Org. Chem. 1980; 45: 2438
8d Wong HN. C, Sondheimer F. Tetrahedron Lett. 1980; 21: 983
8e Huang NZ, Jia J.-H, Wang L.-L, Chan T.-L, Mak TC. W. Tetrahedron Lett. 1982; 23: 4797
8f Chan T.-L, Huang NZ, Sondheimer F. Tetrahedron 1983; 39: 427
8g Chan T.-L, Mak TC. W, Poon C.-D, Wong HN. C, Jia J.-H, Wang L.-L. Tetrahedron 1986; 42: 655
8h Hou X.-L, Wong HN. C. J. Am. Chem. Soc. 1987; 109: 1868

9 Xing YD, Huang NZ. J. Org. Chem. 1982; 47: 140
10 Karle IL, Brockway LO. J. Am. Chem. Soc. 1944; 66: 1974
11 Irngartinger H, Reibel WR. K. Acta Crystallogr., Sect. B 1981; 37: 1724
12 Huang H, Stewart T, Gutmann M, Ohhara T, Niimura N, Li Y.-X, Wen J.-F, Bau R, Wong HN. C. J. Org. Chem. 2009; 74: 359
13 Bachrach SM. J. Org. Chem. 2009; 74: 3609
14 Huang H, Hau C.-K, Law CC. M, Wong HN. C. Org. Biomol. Chem. 2009; 7: 1249
15 Hou X.-L, Huang H, Wong HN. C. Synlett 2005; 1073
16 For a review, see: Iyoda M, Yamakawa J, Rahman MJ. Angew. Chem. Int. Ed. 2011; 50: 10522
17 Peng H.-Y, Lam C.-K, Mak TC. W, Cai Z, Ma W.-T, Li Y.-X, Wong HN. C. J. Am. Chem. Soc. 2005; 127: 9603
18 Lin F, Peng H.-Y, Chen J.-X, Chik DT. W, Cai Z, Wong KM. C, Yam VW. W, Wong HN. C. J. Am. Chem. Soc. 2010; 132: 16383

19a Rajca A, Safronov A, Rajca S, Shoemaker R. Angew. Chem. Int. Ed. Engl. 1997; 36: 488
19b Rajca A, Safronov A, Rajca S, Wongsriratanakul J. J. Am. Chem. Soc. 2000; 132: 3351

20 Hau C.-K, He H, Lee AW. M, Chik DT. W, Cai Z, Wong HN. C. Tetrahedron 2010; 66: 9860
21 Huang NZ, Mak TC. W. J. Chem. Soc., Chem. Commun. 1982; 543

22a Man Y.-M, Mak TC. W, Wong HN. C. J. Org. Chem. 1990; 55: 3214
22b Yang X.-P, Du D.-M, Li Q, Mak TC. W, Wong HN. C. Chem. Commun. 1999; 1607

23 Sygula A, Fronczek FR, Sygula R, Rabideau PW, Olmstead MM. J. Am. Chem. Soc. 2007; 129: 3842
24 Cui J.-F, Chen C, Gao X, Cai Z.-W, Han J.-W, Wong HN. C. Helv. Chim. Acta 2012; 95: 2604

25a Wittig G, Klar G. Justus Liebigs Ann. Chem. 1967; 704: 91
25b Hellwinkel D, Reiff G, Nykodym V. Justus Liebigs Ann. Chem. 1977; 1013

26a Chatt J, Guy RG, Watson HR. J. Chem. Soc. 1961; 2332
26b Eisch JJ, Piotrowski AM, Han KI, Krüger C, Tsay YH. Organometallics 1985; 4: 224
26c Schwager H, Spyroudis S, Vollhardt KP. C. J. Organomet. Chem. 1990; 382: 191
26d Edelbach BL, Lachicotte RJ, Jones WD. J. Am. Chem. Soc. 1998; 120: 2843

27 Wong HN. C, Sondheimer F. Tetrahedron 1981; 37: 99

28a Shibata T, Chiba T, Hirashima H, Ueno Y, Endo K. Angew. Chem. Int. Ed. 2009; 48: 8066
28b Shibata T, Uchiyama T, Hirashima H, Endo K. Pure Appl. Chem. 2011; 83: 597
28c Shibata T, Fujimoto M, Hirashima H, Chiba T, Endo K. Synthesis 2012; 44: 3269

29a Wuckert E, Dix M, Laschat S, Baro A, Schulte JL, Hägele C, Giesselmann F. Liq. Cryst. 2004; 31: 1305
29b Wuckert E, Laschat S, Baro A, Hägele C, Giesselmann F, Luftmann H. Liq. Cryst. 2006; 33: 103
29c Hägele C, Wuckert E, Laschat S, Giesselmann F. ChemPhysChem 2009; 10: 1291
29d Wuckert E, Hägele C, Giesselmann F, Baro A, Laschat S. Beilstein J. Org. Chem. 2009; 5: 57

30 Hau C.-K, Chui SS.-Y, Lu W, Che C.-M, Cheng P.-S, Mak TC. W, Mao Q, Wong HN. C. Chem. Sci. 2011; 2: 1068
31 Rajca A, Rajca S. Angew. Chem. Int. Ed. 2010; 49: 672