Supramolecular Tilt Chirality Derived from Symmetrical Benzene Molecules: Handedness of the 21 Helical Assembly

Chemistry - An Asian Journal - Tập 2 Số 2 - Trang 230-238 - 2007
Akira Tanaka1, Ichiro Hisaki1, Norimitsu Tohnai1, Mikiji Miyata1
1Department of Material and Life Science, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan

Tóm tắt

AbstractAchiral molecules can form aggregates with chirality. This depends on the relative position of the molecules, in other words, the tilt of the molecules (so‐called supramolecular tilt chirality). In this paper, we describe supramolecular chirality appearing in a 21 column composed of symmetrical benzene molecules, which is formed in the host cavity of inclusion crystals of cholic acid. Moreover, we determined the handedness, that is, right or left, of the 21 helical column of benzene on the basis of the molecular tilt. Determination of the 21 helical handedness was performed on assemblies of other benzene derivatives in cholic acid crystals and benzene assemblies in other host frameworks selected from the Cambridge Structural Database. Finally, we demonstrated complementarity of the handedness between the 21 symmetrical host framework of cholic acid and the benzene column.

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Tài liệu tham khảo

 

Lehn J.‐M., 1995, Supramolecular Chemisty: Concepts and Perspectives, 10.1002/3527607439

Steed J. W., 2000, Supramolecular Chemistry

10.1039/b201099m

10.1039/b305550g

2006, Supramolecular Chirality in Top. Curr. Chem., Vol. 265

 

10.1038/35025027

10.1021/cr0000978

10.1021/ja026164s

10.1038/nature01072

10.1002/ange.200504326

10.1002/anie.200504326

Kitaigorodskii A. I., 1973, Molecular Crystals and Molecules

For examples see:

10.1038/343446a0

10.1021/ja0038528

10.1021/cg0341499

10.1002/chem.200400809

Miyata M., 1996, Comprehensive Supramolecular Chemistry, Vol. 6, 147

Miyata M., 2004, Encyclopedia of Supramolecular Chemistry, Vol. 1, 441, 10.1081/E-ESMC-120012746

 

10.1080/15421400590958179

10.1080/15421400590958188

10.1246/cl.2006.806

T. Watabe K. Kobayashi I. Hisaki N. Tohnai M. Miyata Bull. Chem. Soc. Jpn.2007 in press.

For examples see:

10.1038/35012550

10.1002/1521-3757(20020715)114:14<2612::AID-ANGE2612>3.0.CO;2-3

10.1002/1521-3773(20020715)41:14<2502::AID-ANIE2502>3.0.CO;2-9

10.1021/ja038379n

10.1002/ange.200504424

10.1002/anie.200504424

Gardner M., 1999, The New Ambidextrous Universe, 152

10.1021/ja00344a003

For examples see:

10.1002/ange.19961080720

10.1002/anie.199607601

10.1126/science.1060835

For examples see:

10.1126/science.278.5345.1924

10.1039/a702026k

For examples see:

10.1039/b206566p

10.1002/ange.200461431

10.1002/anie.200461431

10.1002/ange.200461833

10.1002/anie.200461833

10.1021/ja0525049

For examples see:

10.1002/chem.19970030517

10.1039/a905245c

10.1039/a808638i

10.1021/ja992432j

10.1039/a909782a

10.1002/ange.200352788

10.1002/anie.200352788

10.1002/chem.200305410

10.1016/j.jphotochemrev.2005.02.002

10.1039/b417771a

1983, International Tables for Crystallography, Vol. A, Space‐Group Symmetry

 

10.1039/b403631j

10.1021/jo0500784

 

10.1021/ja9819918

10.1002/1521-3757(20010417)113:8<1577::AID-ANGE1577>3.0.CO;2-#

10.1002/1521-3773(20010417)40:8<1529::AID-ANIE1529>3.0.CO;2-B

10.1039/b205866a

10.1021/ja039104a

 

10.1246/cl.2006.1274

T. Watabe I. Hisaki N. Tohnai M. Miyata Chem. Lett.2007 in press.

10.1246/cl.1994.137

 

10.1021/ja9807441

10.1021/jo010557c

 

10.1002/1521-3765(20010105)7:1<209::AID-CHEM209>3.0.CO;2-Y

10.1002/ejoc.200200711

10.1039/b210544f

10.1039/b101906f

10.1021/ja00227a067

Caira M. R., 1993, J. Chem. Soc. Chem. Commun., 612, 614

10.1080/10610279608027517

10.1007/BF01673668

10.1007/BF00707690

10.1039/C39940000429

10.1021/ja00121a008

10.1007/BF00707782

10.1023/A:1011833630056

Wyckoff R. W. G., 1969, Crystal Structures, Vol. 6, The Structure of Benzene Derivatives, Vol. 1

10.1126/science.165.3899.1250

 

10.1016/S0022-328X(00)93523-X

10.1021/ja00826a015

Pilati T., 1982, Cryst. Struct. Commun., 11, 1027

10.1016/0022-328X(89)87102-5

10.1021/om00158a024

10.1016/0277-5387(94)00385-R

10.1021/ja026949y

 

10.1002/hlca.19810640543

10.1002/hlca.19920750125

10.1021/om9607614

Ivanov A. V., 1998, Zh. Neorg. Khim., 43, 1482

10.1021/om990195n

10.1002/1521-3765(20010504)7:9<2015::AID-CHEM2015>3.0.CO;2-H

Borowiak T., 2002, Z. Naturforsch., 57, 586, 10.1515/znb-2002-0517

 

10.1023/B:JIPH.0000016589.50470.3c

Watabe T., 2005, Structure and Dynamics in Macromolecular Systems with Specific Interactions, 157

The cross‐section was prepared by the plugin software MDL‐Chime.

1994, The Lock‐and‐Key Principle: Perspectives in Supramolecular Chemistry, Vol. 1

10.1107/S0108768102006675

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Chemistry - An Asian Journal

Tập 2 Số 2

230-238

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