DOI: 10.1002/anie.199207091. Synthetic Bilayer Membranes: Molecular Design, Self‐Organization, and Application

Synthetic Bilayer Membranes: Molecular Design, Self‐Organization, and Application

10.1002/anie.199207091

Crossref journal-article

Wiley

Angewandte Chemie International Edition in English (311)

Abstract

AbstractLipid bilayers are a most central building block of the biological molecular organization. Their two‐dimensional self‐assembly is essential to the generation of biological shapes and sizes on the molecular level. The observation that a totally synthetic amphiphile in water is spontaneously assembled to a bilayer structure suggested that bilayer formation is a general physicochemical phenomenon that is not restricted to particular structures of biolipid molecules. Bilayer formation is now observed for a large variety of synthetic amphiphiles which contain one, two, three, or four alkyl tails. The flexible alkyl tail may be replaced by perfluoroalkyl chains. The supramolecular structures obtained therefrom can be related to the component's molecular structure in many cases. The structural variety and the ease of molecular design make the synthetic bilayer an attractive vehicle for organizing covalently bound functional units and guest molecules. In addition, stable monolayers on water, planar lipid membranes (BLM), and free‐standing cast films are obtainable because of the self‐assembling property of bilayer‐forming compounds. These molecular organizations display common supramolecular features. The use of the cast film as a molecular template provides exciting potential for the production of novel two‐dimensional materials.

Bibliography

Kunitake, T. (1992). Synthetic Bilayer Membranes: Molecular Design, SelfâOrganization, and Application. Angewandte Chemie International Edition in English, 31(6), 709â726. Portico.

Authors 1

Toyoki Kunitake (first)

References 123 Referenced 622

10.1016/S0022-2836(64)80115-7
10.1038/243232a0
10.1021/bi00611a014
{'key': 'e_1_2_1_4_2', 'first-page': '1', 'volume-title': 'Bio Organic Chemistry', 'author': 'Brockerhoff H.', 'year': '1977'} / Bio Organic Chemistry by Brockerhoff H. (1977)
{'key': 'e_1_2_1_5_2', 'volume-title': 'The Hydrophobic Effect, Formation of Micelles, Polymers and Biological Membranes', 'author': 'Tanford C.', 'year': '1973'} / The Hydrophobic Effect, Formation of Micelles, Polymers and Biological Membranes by Tanford C. (1973)
J. N.Israelachvili D. J.Mitchell B. WNinham J. Chem. Soc. Faraday Trans. 21976 1525.
10.1021/ja00453a066
10.1021/ja01183a024
10.1021/j100504a010
{'key': 'e_1_2_1_10_2', 'first-page': '10', 'volume-title': 'Lyotropic Liquid Crystals', 'author': 'Gray G. W.', 'year': '1976'} / Lyotropic Liquid Crystals by Gray G. W. (1976)
{'key': 'e_1_2_1_11_2', 'volume-title': 'Membrane Mimetic Chemistry', 'author': 'Fendler J. H.', 'year': '1982'} / Membrane Mimetic Chemistry by Fendler J. H. (1982)
10.1002/ange.19840960206
10.1002/anie.198401001
10.1002/ange.19881000111
10.1002/anie.198801131
T.Kunitake Y.Okahata K.Tamaki F.Kumamaru M.Takayanagi Chem. Lett.1977 387. (10.1246/cl.1977.387)
10.1016/0021-9797(78)90267-9
10.1016/0009-2614(79)80511-4
10.1021/ja00509a001
10.1021/ja00509a002
10.1016/0005-2736(83)90103-7
T.Kunitake Y.Okahata Chem. Lett.1977 1337. (10.1246/cl.1977.1337)
T.Kunitake N.Nakashima S.Hayashida K.Yonemori Chem. Lett.1979 1413. (10.1246/cl.1979.1413)
10.1021/ja00527a061
{'key': 'e_1_2_1_23_2', 'first-page': '4235', 'volume': '102', 'author': 'Murakami Y', 'year': '1980', 'journal-title': 'J. Am. Chem. Soc.'} / J. Am. Chem. Soc. by Murakami Y (1980)
10.1002/ange.19810930918
10.1002/anie.198108041
T.Kunitake M.Shimomura Y.Hashiguchi T.Kawanaka J. Chem. Soc. Chem. Commun.1985 833. (10.1039/c39850000833)
10.1246/bcsj.51.1877
10.1016/0006-291X(78)91246-9
10.1016/0021-9797(81)90382-9
10.1007/978-1-4615-6743-1_53
K.Okuyama Y.Soboi K.Hirabayashi A.Harada A.Kumano T.Kajiyama M.Takayanagi T.Kunitake Chem. Lett.1984 2117. (10.1246/cl.1984.2117)
10.1246/bcsj.61.1485
10.1246/bcsj.61.2337
H.Okada Kyushu University unpublished.
10.1021/j100367a062
10.1002/bbpc.19810850811
{'key': 'e_1_2_1_36_2', 'first-page': '221', 'volume': '46', 'author': 'Kunitake T.', 'year': '1986', 'journal-title': 'Mem. Fac. Eng. Kyushu Univ.'} / Mem. Fac. Eng. Kyushu Univ. by Kunitake T. (1986)
{'key': 'e_1_2_1_37_2', 'first-page': '93', 'volume': '49', 'author': 'Kim J.‐M.', 'year': '1989', 'journal-title': 'Mem. Fac. Eng. Kyushu Univ.'} / Mem. Fac. Eng. Kyushu Univ. by Kim J.‐M. (1989)
M.Shimomura T.Kunitake Chem. Lett.1981 1001. (10.1246/cl.1981.1001)
10.1021/ja00370a061
10.1021/ja00357a018
{'key': 'e_1_2_1_41_2', 'first-page': '71', 'volume-title': 'Biological Membranes', 'author': 'Luzzati V.', 'year': '1968'} / Biological Membranes by Luzzati V. (1968)
Y Murakami A.Nakano J.Kikuchi T.Takaki K.Uchimura Chem. Lett.1983 1891. (10.1246/cl.1983.1891)
10.1021/ja00293a055
10.1246/bcsj.59.515
10.1021/ja00295a012
10.1021/ja00274a011
10.1007/BF01869487
10.1016/S0006-3495(86)83501-9
10.1021/j100274a005
10.1016/0022-2836(84)90234-1
N.Nakashima S.Asakuma T.Kunitake H.Hotani Chem. Lett.1984 227. (10.1246/cl.1984.227)
{'key': 'e_1_2_1_52_2', 'volume': '1911', 'author': 'Kimizuka N.', 'year': '1988', 'journal-title': 'Chem. Lett.'} / Chem. Lett. by Kimizuka N. (1988)
10.1021/ja00522a019
10.1002/bbpc.19830871211
10.1002/bbpc.19800840607
Y.Okahata H.Ihara M.Shimomura S.Tawaki T.Kunitake Chem. Lett.1980 1169. (10.1246/cl.1980.1169)
10.1021/ja00408a021
M.Shimomura H.Hashimoto T.Kunitake Chem. Lett.1982 1285. (10.1246/cl.1982.1285)
{'key': 'e_1_2_1_59_2', 'first-page': '245', 'volume': '46', 'author': 'Kunitake T.', 'year': '1986', 'journal-title': 'Mem. Fac. Eng. Kyushu Univ.'} / Mem. Fac. Eng. Kyushu Univ. by Kunitake T. (1986)
I.Cho J. G.Park Chem. Lett.1987 977. (10.1246/cl.1987.977)
T.Kunitake N.Yamada N.Fukunaga Chem. Lett.1984 1089. (10.1246/cl.1984.1089)
10.1007/978-1-4684-2793-6_12
10.1016/0040-6090(84)90060-9
{'key': 'e_1_2_1_64_2', 'first-page': '2407', 'volume': '38', 'author': 'Xu G.', 'year': '1989', 'journal-title': 'Polym. Prepr. Japan'} / Polym. Prepr. Japan by Xu G. (1989)
10.1246/bcsj.59.3351
H.Watanabe K.Okuyama H.Ozawa K.Hirabayashi M.Shimomura T.Kunitake N.Yasuoka Nippon Kagaku Kaishi1988 55.
10.1246/bcsj.62.3211
10.1016/0169-4332(88)90449-7
10.1295/polymj.18.281
Y.Ishikawa T.Nishimi T.Kunitake Chem. Lett.1990 165. (10.1246/cl.1990.165)
10.1021/ja00319a014
N.Kimizuka H.Ohira M.Tanaka T.Kunitake Chem. Lett.1990 29. (10.1246/cl.1990.29)
10.1016/0005-2760(81)90038-2
10.1021/ja00512a020
S.Yasunami Masters Thesis Kyushu University 1980.
10.1002/ange.19800920721
10.1002/anie.198005501
10.1021/ja00268a013
10.1295/polymj.17.633
10.1021/ja00384a073
10.1246/bcsj.56.3235
10.1002/macp.1985.020141985108
10.1021/ja00289a025
10.1021/j100553a028
10.1021/ja00541a081
T.Kunitake N.Nakashima K.Morimitsu Chem. Lett.1980 1347. (10.1246/cl.1980.1347)
N.Nakashima S.Asakuma J.‐M.Kim T.Kunitake Chem. Lett.1984 1709. (10.1246/cl.1984.1709)
10.1021/ja00288a043
Y Ishikawa T.Nishimi T.Kunitake Chem. Lett.1990 25. (10.1246/cl.1990.25)
T.Kunitake N.Yamada J. Chem. Soc. Chem. Commun.1986 655. (10.1039/c39860000655)
K.Yamada H.Ihara T.Ide T.Fukumoto Chem. Lett.1984 1713. (10.1246/cl.1984.1713)
J.‐M.Kim Y.Ishikawa T.Kunitake J. Chem. Soc. Perkin Trans. 2 1991 885.
10.1080/00268948408071454
10.1016/0009-3084(85)90011-8
10.1021/ja00228a037
10.1016/0014-5793(81)81187-8
10.1021/bi00408a009
10.1021/ja00174a063
10.1021/ja00025a031
10.1002/ijch.198800006
Y.Murakami Y.Hisaeda T.Ohno Y.Matsuda Chem. Lett.1986 731. (10.1246/cl.1986.731)
{'key': 'e_1_2_1_101_2', 'first-page': '141', 'volume': '11', 'author': 'Kunitake T.', 'year': '1987', 'journal-title': 'New J. Chem.'} / New J. Chem. by Kunitake T. (1987)
10.1021/la00096a028
10.1021/ja00251a022
N.Nakashima R.Ando H.Fukushima T.Kunitake J. Chem. Soc. Chem. Commun.1982 707. (10.1039/c39820000707)
10.1021/ja00262a040
10.1016/0166-6622(89)80145-3
S.Kato T.Kunitake Chem. Lett.1991 261. (10.1246/cl.1991.261)
N.Nakashima R.Ando T.Kunitake Chem. Lett.1983 1577. (10.1246/cl.1983.1577)
10.1073/pnas.64.1.20
10.1021/ac00194a014
10.1021/ja00262a040
10.1021/ja00002a034
S.Asakuma T.Kunitake Chem. Lett.1989 2059. (10.1246/cl.1989.2059)
10.1021/ja00005a044
K.Sakata T.Kunitake Chem. Lett.1989 2159. (10.1246/cl.1989.2159)
K.Sakata T.Kunitake J. Chem. Soc. Chem. Commun.1990 504. (10.1039/c39900000504)
10.1021/cm00008a001
10.1021/ja00204a042
Y.Ishikawa H.Kuwahara T.Kunitake Chem. Lett.1989 1737. (10.1246/cl.1989.1737)

Dates

Type	When
Created	21 years, 7 months ago (Dec. 30, 2003, 6:12 p.m.)
Deposited	1 year, 10 months ago (Oct. 23, 2023, 5:02 a.m.)
Indexed	4 days ago (Aug. 20, 2025, 9:15 a.m.)
Issued	33 years, 2 months ago (June 1, 1992)
Published	33 years, 2 months ago (June 1, 1992)
Published Online	21 years, 8 months ago (Dec. 22, 2003)
Published Print	33 years, 2 months ago (June 1, 1992)

Funders 0

None

BibTeX

@article{Kunitake_1992, title={Synthetic Bilayer Membranes: Molecular Design, Self‐Organization, and Application}, volume={31}, ISSN={0570-0833}, url={http://dx.doi.org/10.1002/anie.199207091}, DOI={10.1002/anie.199207091}, number={6}, journal={Angewandte Chemie International Edition in English}, publisher={Wiley}, author={Kunitake, Toyoki}, year={1992}, month=jun, pages={709–726} }

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