Tribute to Toyoki Kunitake - Langmuir (ACS Publications)


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Tribute to Toyoki Kunitake Saburo Akiyoshi and Prof. Chuji Aso, professors of synthetic chemistry. Dr. Kunitake then moved to work under Prof. C. C. Price at the University of Pennsylvania, where he obtained his Ph.D. in 1962. A post-doctoral year (bioorganic chemistry and enzyme reactions) followed with Prof. C. G. Nieman in theDepartment of Chemistry, California Institute of Technology. In 1963, he returned to the Department of Synthetic Chemistry, Kyushu University as an associate professor under the guidance of Prof. Chuji Aso. He initiated a study on mechanistic aspects of cationic polymerization, focusing, among other, on the phenomenon of stereoregularity and how to control it. After his promotion to full professor in 1974, his research interests changed to the design of polymer catalysts for use in aqueous media, based on the model of enzymatic hydrolysis. He prepared several vinyl polymers having a hydrophobic site acting as the substrate binding pocket and a functional group, such as an imidazole, acting as a nucleophile. They represent the first examples of synthetic polymer catalysts showing a substrate binding process. He went on to prepare other bifunctional polymer catalysts and contributed to the development of enzymatic models for catalysis in micellar and macromolecular systems. This body of work had a significant impact on bioorganic chemistry, polymer catalysis, and colloid and surface science. In 1977, Dr. Kunitake discovered that synthetic organic molecules could spontaneously form a bilayer membrane, the basic structure common to the biological membranes of living cells. His first report of a “Totally Synthetic Bilayer Membrane” became a landmark article that has been cited more than 320 times. His subsequent research established the formation of bilayer membranes as a universal phenomenon, observed not only in water but also in organic solvents, for synthetic amphiphilic compounds with various precisely designed molecular structures. His group synthesized hundreds of amphiphilic molecules, including cationic, anionic, nonionic, and zwitterionic hydrophilic headgroups in combination with two, three, and four alkyl or perfluoroalkyl chains. He systematized the mechanism of synthetic bilayer membrane formation through his unique organic chemistry-based research methodology combined with various physicochemical characterization techniques. He also developed methods to immobilize bilayer membranes and to produce various self-assembling materials. Through these approaches, he opened up a new and promising academic field of chemistry based on molecular self-assembly. In 1982, Dr. Kunitake reported the fabrication of immobilized bilayer films in which synthetic bilayer membranes were fixed with polymers by casting from organic solutions. This was the first example of self-standing molecular self-assembled films. He extended this idea to lipid−inorganic composite films prepared from alkoxysilane or silica gels. Dr. Kunitake’sapproach to synthetic bilayer membranes was revolutionary, overturning the previously held assumption that

This issue is a tribute to Dr. Toyoki Kunitake, a pioneer in the chemistry of molecular self-assembly, a topic of great interest to the Langmuir readership. Dr. Kunitake was born in Kurume City in Fukuoka Prefecture, Kyushu, Japan on February 26, 1936. Following a high school education, he entered the Department of Applied Chemistry, Faculty of Engineering, Kyushu University in 1958. He graduated with B.Sc. (1962) and MSc. (1964) degrees, with a focus on polymer synthesis. His B.Sc. and MSc. supervisors were Prof. © 2016 American Chemical Society

Special Issue: Tribute to Toyoki Kunitake, Pioneer in Molecular Assembly Published: November 29, 2016 12231

DOI: 10.1021/acs.langmuir.6b03904 Langmuir 2016, 32, 12231−12241

Langmuir



ordered molecular self-organized structures such as biological membranes could be formed only by biolipids in nature. His research made it possible, for the first time, to gain a molecular design-based understanding of how molecularly organizational structures and physical properties, which are created in a hierarchical manner through self-assembly, correlate with the molecular structures of components. While extending the formation of molecular self-assembly from aqueous to organic solvents, he generalized the conventional image of hydrophilic and hydrophobic portions of amphiphilic molecules. Dr. Kunitake also showed that specific interactions among functional groups derived from advanced ordered structures appear in bilayer membranes, thereby establishing the fundamental concept of chemistry based on self-assembly where interactions on the molecular level lead to collective functions that are controlled according to molecular orientation and distribution. He converted this fundamental understanding to innovations in materials science as a director of the ERATO molecular architecture project (JST, 1987−1992), the ICORP supramolecular project (1992−1997), and the Group Director of the RIKEN Frontier Research System (1999−2007). Dr. Kunitake’s major achievements toward innovation include the following: (1) the development of various methods for bilayer membrane immobilization, thereby enabling the creation of precisely organized membranes; bilayer membranes immobilized in this way are used to produce superlaminated solid molecular-oriented film electrodes in fully automated electrolyte analyzers for medical use and in vitro diagnostic testing; (2) the development of a molecular self-assembly-based synthetic methodology for two-dimensional polymers and two-dimensional ultrathin silica films by using organic molecular assemblies as templates; their microstructures follow the morphologies used as templates; (3) the discovery of a technique for manufacturing large, free-standing nanostructured thin films, the giant nanomembrane, which possesses notable strength as well as extreme flexibility. These characteristics had long been sought in the field of functional membranes, and at present, there are high expectations for their wide-ranging applications, including fuel cells and gas and water separation, which can contribute to solutions for environmental problems. Through these achievements, Dr. Kunitake has converted the concept of molecular self-assembly-based chemistry into one of the most useful methodologies in advanced functional materials design and has reached a new frontier in the field of materials science using self-assembly techniques. At the same time, he has trained a large number of highly accomplished researchers in these academic fields as well as industry and has made an invaluable contribution to international academic exchange. Dr. Kunitake also served as the Dean of the Faculty of Engineering, Kyushu University for 1992−1994; Professor and Vice President, University of Kitakyushu for 1999−2008; and President of the Kitakyushu Foundation for the Advancement of Industry, Science and Technology, for 2009−2016. Dr. Kunitake is currently a University Professor of Kyushu University. He has received numerous honors, including the Medal with Purple Ribbon, Order of Culture, Japan in 1999; the Japan Academy Prize in 2001; an H. C. Brown Lectureship, Purdue University in 2000; Alexander Memorial Lecturer, University of Sydney, 2001; and Order of Culture, Japan in 2014. This special issue of Langmuir is dedicated to the Kyoto Prize he received in 2015 and his 80th birthday. We thank all of the authors who contributed to this special issue.

Preface

COLLEAGUES OF PROFESSOR TOYOKI KUNITAKE

Graduate Ph.D. Students (Chronological Order). Yoshio Okahata (1977) Katsuhiro Harada (1979) Tetsuo Sakamoto (1979) Kunihide Takarabe (1980) Naotoshi Nakashima (1981) Hirotaka Ihara (1982) Masatsugu Shimomura (1984) Akihiko Tsuge (1985) Norihiro Yamada (1985) Yuichi Ishikawa (1987) Jong-Mok Kim (1989) Masashi Kunitake (1989) Nobuo Kimizuka (1990) Shiji Kato (1991) Michiya Fujiki (1992) Taisei Nishimi (1992) Hiroaki Kuwahara (1993) Hidetoshi Fujimura (1994) Atsushi Watakabe (1994) Akio Fujita (1995) Izumi Ichinose (1995) Takayoshi Kawasaki (1995) Shigenori Fujikawa (1998) Munetoshi Isayama (1998) Takashi Iwamoto (1998) Seung-Woo Lee (1998) Mitsuhiko Onda (1998) Eiji Watanabe (1999) Faculty Staff at Kyushu University (Chronological Order). Seiji Shinkai (1972−1975 Lecturer, 1975−1976 Associate Professor) Yoshio Okahata (1972−1979 Assistant Professor, 1979−1980 Lecturer) Kunihide Takarabe (1973−1980 Assistant Professor) Naotoshi Nakashima (1980−1982 Assistant Professor, 1982− 1987 Associate Professor) Nobuyuki Higashi (1982−1985 Assistant Professor, 1985− 1987 Associate Professor) Masatsugu Shimomura (1980−1985 Assistant Professor) Norihiro Yamada (1985−1986 Assistant Professor) Yuichi Ishikawa (1987−1989 Assistant Professor, 1989−1994 Associate Professor) Nobuo Kimizuka (1985−1992 Assistant Professor, 1992− 2000 Associate Professor) Itaru Hamachi (1988−1992 Assistant Professor) Izumi Ichinose (1992−2000 Assistant Professor) Tetsu Yonezawa (1998−2001 Assistant Professor) Reiko Ando (1986−2007 Technical Assistant) Postdoctoral Students and Visiting Researchers at Kyushu University (Alphabetical Order). Robert Hall Akio Hayashi Hikaru Horimoto Robert R. Johnston Sang Ho Lee Werner Prass Keiji Yamada Research Staff for the JST ERATO Project (Japan Science and Technology Agency; JST, E Exploratory 12232

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Langmuir Research for Advanced Technology; ERATO) (Alphabetical Order). Sumitoshi Asakuma Yuichi Arito Lee Burm-Jong Peter Berndt Hisao Furusawa Kenji Fukuda Hiromi Fukuda Naoki Hatta Daikichi Horiguchi Kimiyo Hirayama Yoshihiro Honda Jong-Dal Hong Munetoshi Isayama Yasuhiro Ikeura Yasuo Itami Katsuhisa Koyama Tatsuo Kusano Kazue Kurihara Takaharu Kawahara Shinji Kato Paul S. Lugg Miroslav Marek Timothy P. Newcomb Kaori Ohto Hideo Okada Akio Okizaki Akemi Okubo Hiroshi Okusa Masahito Sano Kanji Sakata Ryuichi Shimizu Yukiko Sasaki Darryl Y. Sasaki Yoshiyuki Takeda Miki Tahara Nobuo Tsutsumi Hitomi Tanaka Hideo Tamamura Tetsuo Ueno Naoto Wazima Atsushi Watakabe Kyoko Watanabe Yutaka Wakayama Masayuki Yanagi Research Staff at JST ICORP (Japan Science and Technology Agency; JST, International Cooperative Research Project; ICORP) (Alphabetical Order). Takahisa Anada Katsuhiko Ariga Philippe Bissel Xiao Cha Karen Grieve Ayumi Kamino Erik Kelderman Hiroshi Koyano Miki Kuboyama Yuri Lvov Valerie Marchi-Artzner Takao Maruyama Mitsuhiko Onda Kazuhiro Taguchi

Yoshimi Ushijima Kanami Yoshihara Research Staff for the Topochemical Design Research Team in RIKEN (Alphabetical Order). Yoshitaka Aoki Shigenori Fujikawa Acharya Ghanshyam Mineo Hashizume Junhui He Jianguo Huang Izumi Ichinose Haibin Li Yuanzhi Li Wei Liang Emi Muto Junqi Sun Rie Takaki Hirohmi Watanabe Research Staff at NanoMembrane Technologies, Inc. (Chronological Order). Yoshikuni Kunitake Shigenori Fujikawa Hirohmi Watanabe Kensaku Nagasawa Minako Tajima Chihoko Fukakusa Harumi Hayakawa Ako Shimada Miho Ariyoshi Suzuka Endo Rie Tomimatsu Collaborators as Paper Coauthors (Alphabetical Order). Tetsuyuki Akao Shoji Ando Yasuhiro Aoyama Kazuma Araki Tomoaki Arimura Tsutomu Asai Sumitoshi Asakuma Chuji Aso Atsushi Baba Veronique Birault Thomas C. Bruice Frank Caruso Irving R. Epstein Masanao Era Kotaro Fujimura Kunitaka Fujiyoshi Kiyoshige Fukuda Nobuto Fukunaga Yuichi Fukushige Hiroshi Fukushima Wataru Furagami D. Neil Furlong Takao Furuki Hiroyuki Furuta Wataru Futagami Franz Grieser Hiroki Habazaki Hisatake Hamada Mitsuo Hamada Toyokazu Handa 12233

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Langmuir Suguru Kodaira Michiko Kodama Jun-ichi Koganemaru Serhiy O. Korposh Kazuya Koumoto Toshio Kubota Yoshitaka Kudo Fumiko Kumamaru Atsushi Kumano Miyuki Kuramori Keiji Kurashima Keita Kuroiwa Yumiko Kusano Naoshi Kusumoto Masami Kusunoki Michal Lahav Chang-Soo Lee Jean-Marie Lehn Shuxia Liu Xiangmei Liu Aya Maeda Tadashi Maeda Syoichi Makimoto Osamu Manabe Andrew Marsh Hiroshi Masuhara Tsutomu Matsuda Yoshihiko Matsuguma Takahiro Matsumoto Hideki Matsune Taku Matsuo Sachiko Matsushita Junya Mitoma Masanobu Miura Hiroyuki Miyagi Haruko Miyauchi Hirotoshi Miyazaki Reiko Miyazoe Kentaro Miyoshi Takanori Miyoshi Masami Mizu Suguru Mizuki Tohru Mizushima Naoki Mizutani J. Moellerfeld Kozo Morimitsu Naoaki Morotomi Yoshiaki Motozato Shigeru Murakami Tsuyoshi Muramatsu Hiroko Murata Masaru Nagai Shinji Nagata Hiroo Nakahara Hiroshi Nakamura Kentaro Nakamura Mitsugi Nakamura Shinichiro Nakamura Aiko Nakao Yoichi Nakatani Youichi Nakayama Takayuki Narita Carl Niemann

Akihisa Harada Akira Harada Atsushi Harada Masakazu Hase Yuichi Hashiguchi Hiromasa Hashimoto Yasuhiro Hashimoto Yasuhiro Hatanaka Kenshi Hayashi Seiji Hayashi Shoichi Hayashida George E. Hein Shoichi Higuchi Takeshi Higuchi Kiyoshi Hirabayashi Shinichi Hirakawa Yuji Hirano Shoji Hiraoka Kiyoko Hirata Chuichi Hirayama Sumio Hirotsu Shuichi Honda Tatsuya Honda Seiji Horie Hirokazu Hotani Toyoko Ide Kazutoshi Iida Naomi Iijima Satoru Iiyama Kuniharu Ijiro Yoji Imaizumi Takashi Imamura Hiroo Inokuchi Hironori Inoue Yoshio Inoue Teruya Ishihara Yoshikazu Ishimoto Akira Ishitani Nobuaki Isono Akira Itaya Akio Ito Kenji Ito Hiroaki Iwasaki J. Bryan Jones Myung-Jong Ju Tisato Kajiyama Carina Kamaga Koji Kano Ryouji Karinaga Tsutomu Katayama Takayuki Kato Orit Katz Takeshi Kawai Takeshi Kawakami Takafumi Kawanaka Osamu Kawano Walter E. Keller Andrei B. Kharitonov Rangin K. Khattak Takashi Kikuchi Taro Kimura Ryuji Kita Hideki Kobayashi 12234

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Langmuir Kazuaki Suehiro Norio Sugi Hiroaki Sugimoto Mizuki Sutoh Iwao Tabushi Masami Tachikawa Toyohide Tahara Takayuki Takahagi Atsushi Takahara Naoki Takahara Motowo Takangi Takahiro Takasaki Motowo Takayanagi Hiromi Takemoto Katsuhisa Watanabe Takeshi Watanabe Itamar Willner Guiqint Xu Hiroshi Yabu Tatsuhiko Yagi Shinji Yamada Sunao Yamada Tetsuhiro Yamada Kaoru Yamafuji Katsuhiko Yamaguchi Shu Yamaguchi Tomohiko Yamaguchi Tomoharu Yamami Kouji Yamamoto Akihiro Yanagi Do-Hyeon Yang Masaharu Yasumatsu Shoichiro Yasunami Noritake Yasuoka Kazuyuki Yonemori Takeshi Yoshimi Satoru Yoshimura Susumu Yoshimura Liangren Zhang Shen Zhang

Takako Nishiya Masazo Niwa Osamu Niwa Shunsaku Noda Kazuko Normiyama Munenori Numata Eishi Obana Takeharu Ochiai Noriko Oda Kota Ogawa Teiichiro Ogawa Osamu Ohara Hiroyuki Ohira Shinji Ohno Takuya Ohzono Yushi Oishi Hisashi Okawa Naoto Oki Kenji Okuyama Nobuaki Ono Shin-ya Onoue Tetsurou Osaki Toshio Otsuka Guy Ourisson Kazunari Ozasa Satoshi Ozawa Yutaka Ozawa Fotios Papadimitrakopoulos Gianluca Pozzi Jeremy J. Ramsden Helmut Ringsdorf James F. Rusling Kenzaburo Saiki Shogo Saito Hiroshi Sakaguchi Daisuke Sakemi Kazuo Sakurai Minoru Sakurai Makoto Sasaki Sono Sasaki Tazuko Sasaki Eiko Satoh Tetsuro Sawadaishi David Scoberg Syuzo Seki Kazuhisa Sekimizu Mari Sekita Roman Selyanchyn Hiroyuki Senzu Masayo Shiba Tomoko Shibata Yasuhisa Shibata Fumiko Shimada Masafumi Shimizu Hiroto Shimokawa Yoshikazu Shimoto Jae Sup Shin Masatake Shinsenji Hiroaki Shiraishi Sumihiro Shiraishi Yukihide Shiraishi Yoshie Soboi Fusami Soeda



CURRICULUM VITAE Brief Biography of Prof. Toyoki Kunitake Date of Birth: February 26, 1936, in Fukuoka, Japan 1960 Master of Engineering, Department of Applied Chemistry, Graduate School of Engineering, Kyushu University 1962 Ph.D. Department of Chemistry, University of Pennsylvania (Supervisor, Charles C. Price) 1962 Postdoctoral Fellow, California Institute of Technology (with Prof. Carl G. Niemann) 1963 Associate Professor, Faculty of Engineering, Kyushu University 1974 Professor, Faculty of Engineering, Kyushu University 1989−1992 Research Director, JST ERATO “Kunitake Molecular Architecture Project” 1992−1994

Dean, Faculty of Engineering, Kyushu University

1992−1996

Research Director, JST International Cooperative Research Project (ICORP), Supermolecules Project Project Leader, Grant-in-aid for Scientific Research on Priority Area, Ministry of Education, Culture, Sports, Science and Technology-Japan Professor and Vice President, The University of Kitakyushu

1996−1999

1999 12235

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Langmuir 1999−2005 1999−2007 2007−present 2009−2016 2012−present 2012−present 2016−present Social Activities 1996−1997 1997−1998 Selected Awards 1978 1990 1996 1998 1999 2001 2007 2011 2014 2015

Research Supervisor, JST PREST “Organization and Function” Group Director, Spatio-Temporal Function Materials Research Group, Frontier Research System, RIKEN Director, NanoMembrane Technologies, Inc. President, Kitakyushu Foundation for the Advancement of Industry, Science and Technology WPI Professor, International Institute for CarbonNeutral Energy Research, Kyushu University Research Supervisor, JST ACT-C (Advanced Catalytic Transformation Program for Carbon Utilization) University Professor, Institute for Advanced Study, Kyushu University

8. Kunitake, T.; Okahata, Y. Multifunctional hydrolytic catalyses. 7. Cooperative catalysis of the hydrolysis of phenyl esters by a copolymer of N-methylacrylohydroxamic acid and 4vinylimidazole. J. Am. Chem. Soc. 1976, 98, 7793−7799. 9. Kunitake, T.; Okahata, Y. Multifunctional hydrolytic catalyses. IV. The catalytic hydrolysis of p-nitrophenyl acetate by copolymers containing complementary functional groups (hydroxamate and imidazole). Macromolecules 1976, 9, 15−22. 10. Shinkai, S.; Ide, T.; Hamada, H.; Manabe, O.; Kunitake, T. Influence of magnesium dication on the reduction of Nmethylacridinium ion with 1,4-dihydronicotinamide. J. Chem. Soc., Chem. Commun. 1977, 848−849. 11. Okahata, Y.; Ando, R.; Kunitake, T. Nucleophilic ion pairs. 4. Remarkable activation of anionic nucleophiles toward pnitrophenyl acetate by aqueous trioctylmethylammonium chloride: a new class of the hydrophobic aggregate. J. Am. Chem. Soc. 1977, 99, 3067−3072. 12. Kunitake, T.; Okahata, Y. A totally synthetic bilayer membrane. J. Am. Chem. Soc. 1977, 99, 3860−3861. 13. Kunitake, T.; Okahata, Y.; Tamaki, K.; Kumamaru, F.; Takayanagi, M. Formation of the bilayer membrane from a series of quaternary ammonium salts. Chem. Lett. 1977, 387−390. 14. Kunitake, T.; Sakamoto, T. Catalytic hydrolysis of phenyl esters in aqueous didodecyldimethylammonium vesicles: remarkable rate difference between intra- and intervesicle reactions. J. Am. Chem. Soc. 1978, 100, 4615−4617. 15. Shinkai, S.; Nakashima, N.; Kunitake, T. Nucleophilic ion pairs. 5. Facile cleavage of amide substrates by a hydroxamate anion in aprotic solvents. Efficient inhibition by minute amounts of water. J. Am. Chem. Soc. 1978, 100, 5887−5892. 16. Shinkai, S.; Yamada, S.; Kunitake, T. Coenzyme models. 10. Rapid oxidation of NADH by a flavin immobilized in cationic polyelectrolytes. Macromolecules 1978, 11, 65−68. 17. Kunitake, T.; Takarabe, K. Determination of the rate constants of the elementary steps in the cationic polymerization of styrene by trifluoromethanesulfonic acid. Macromolecules 1979, 12, 1061−1067. 18. Kunitake, T.; Takarabe, K. Determination of rate constants of free-ion and paired-ion propagations in the cationic polymerization of styrene by trifluoromethanesulfonic acid. Macromolecules 1979, 12, 1067−1071. 19. Okahata, Y.; Kunitake, T. Formation of stable monolayer membranes and related structures in dilute aqueous solution from two-headed ammonium amphiphiles. J. Am. Chem. Soc. 1979, 101, 5231−5234. 20. Tsukino, M.; Kunitake, T. Radical cyclopolymerization of divinyl ether. The microstructure of the polymer and the cyclopolymerization mechanism. Macromolecules 1979, 12, 387− 391. 21. Kunitake, T.; Okahata, Y.; Ando, R.; Shinkai, S.; Hirakawa, S. Decarboxylation of 6-nitrobenzisoxazole-3-carboxylate catalyzed by ammonium bilayer membranes. A comparison of the catalytic behavior of micelles, bilayer membranes, and other aqueous aggregates. J. Am. Chem. Soc. 1980, 102, 7877−7881. 22. Kunitake, T.; Okahata, Y. Formation of the stable bilayer assemblies in dilute aqueous solution from ammonium amphiphiles with the diphenylazomethine segment. J. Am. Chem. Soc. 1980, 102, 549−553. 23. Kunitake, T.; Okahata, Y.; Shimomura, M.; Yasunami, S.; Takarabe, K. Formation of stable bilayer assemblies in water from single-chain amphiphiles. Relationship between the amphiphile structure and the aggregate morphology. J. Am. Chem. Soc. 1981, 103, 5401−5413.

Vice President, The Chemical Society of Japan Vice President, The Society of Polymer Science, Japan and Honors The Award of the Society of Polymer Science, Japan The Chemical Society of Japan Award The Mukai Prize, Tokyo Ohka Foundation for The Promotion of Science and Technology SPSJ Award for Outstanding Achievement in Polymer Science and Technology Medal with Purple Ribbon, Government of Japan Japan Academy Prize Person of Cultural Merit, Government of Japan. The Order of the Sacred Treasure, Gold and Silver Star, Government of Japan Order of Culture, Government of Japan Kyoto Prize, The Inamori Foundation "Pioneering Contributions to the Materials Sciences by Discovering Synthetic Bilayer Membranes and Creating the Field of Chemistry Based on Molecular SelfAssembly”



SELECTED PUBLICATIONS OF TOYOKI KUNITAKE 1. Aso, C.; Kunitake, T.; Shinkai, S. Hydrolysis of a phenyl ester catalyzed by a hydrophobic imidazole derivative in an aqueous system: enzyme model. Chem. Commun. 1968, 1483−1485 2. Kunitake, T.; Shimada, F.; Aso, C. Imidazole catalyses in aqueous systems. I. Enzyme-like catalysis in the hydrolysis of a phenyl ester by imidazole-containing copolymers. J. Am. Chem. Soc. 1969, 91, 2716−2723. 3. Kunitake, T.; Shinkai, S. Imidazole catalyses in aqueous systems. VI. Enzyme-like catalysis in the hydrolysis of a phenyl ester by phenylimidazole-containing copolymers. Correlation between binding capacity and catalytic activity. J. Am. Chem. Soc. 1971, 93, 4256−4263. 4. Kunitake, T.; Shinkai, S. Imidazole catalyses in aqueous systems. V. Enzyme-like catalysis in the hydrolysis of a phenyl ester by copolymers containing a benzimidazole group. Rate acceleration by bound phenols and the mode of side chain aggregation in polymer catalysts. J. Am. Chem. Soc. 1971, 93, 4247−4255. 5. Shinkai, S.; Kunitake, T.; Bruice, T. C. Importance of 1,2enediols in the reduction of lumiflavin by alpha-ketols. J. Am. Chem. Soc. 1974, 96, 7140−7142. 6. Kunitake, T.; Tsugawa, S. Preparations of triphenylmethyl salts and their use in the cationic polymerization of alphamethylstyrene. Counteranion and polymer structure. Macromolecules 1975, 8, 709−713. 7. Kunitake, T.; Okahata, Y.; Sakamoto, T. Multifunctional hydrolytic catalyses. 8. Remarkable acceleration of the hydrolysis of p-nitrophenyl acetate by micellar bifunctional catalysts. J. Am. Chem. Soc. 1976, 98, 7799−7806. 12236

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acidic aqueous solution/carbon tetrachloride interface. Langmuir 1988, 4, 1064−1066. 42. Tian, Y.; Isono, N.; Kawai, T.; Umemura, J.; Takenaka, T.; Kunitake, T. pH dependence of UV-vis absorption and resonance Raman spectra of an aqueous solution of an azobenzene-containing ammonium amphiphile. Langmuir 1988, 4, 693−696. 43. Ishikawa, Y.; Kuwahara, H.; Kunitake, T. Self-assembly of bilayer membranes in organic solvents by novel amphiphilic compounds. J. Am. Chem. Soc. 1989, 111, 8530−8531. 44. Kunitake, T.; Nakashima, N.; Kunitake, M. Polymerization and membrane characteristics of aqueous bilayers of glutamatebased double-chain ammonium amphiphiles. Macromolecules 1989, 22, 3544−3550. 45. Kimizuka, N.; Kunitake, T. Specific assemblies of the naphthalene unit in monolayers and the consequent control of energy transfer. J. Am. Chem. Soc. 1989, 111, 3758−3759. 46. Uchida, M.; Kunitake, T.; Kajiyama, T.; Tanizaki, T. Surface stability and functional property of polymerized Langmuir-Blodgett type films. Macromolecules 1989, 22, 2381− 2387. 47. Kunitake, T.; Higashi, N.; Kunitake, M.; Fukushige, Y. Permeation of aqueous potassium bromide through LangmuirBlodgett films of singly and doubly polymeric monolayers. Macromolecules 1989, 22, 485−487. 48. Shimomura, M.; Hashimoto, H.; Kunitake, T. Controlled stilbene photochemistry in ammonium bilayer membranes. Langmuir 1989, 5, 174−180. 49. Hamachi, I.; Noda, S.; Kunitake, T. Layered arrangement of oriented myoglobins in cast films of a phosphate bilayer membrane. J. Am. Chem. Soc. 1990, 112, 6744−6745. 50. Sakata, K.; Kunitake, T. A multilayered film of an ultrathin siloxane network. J. Chem. Soc., Chem. Commun. 1990, 504−505. 51. Okada, H.; Sakata, K.; Kunitake, T. Formation of oriented iron oxide particles in cast multibilayer films. Chem. Mater. 1990, 2, 89−91. 52. Hamachi, I.; Noda, S.; Kunitake, T. Functional conversion of myoglobin bound to synthetic bilayer membranes: from dioxygen storage protein to redox enzyme. J. Am. Chem. Soc. 1991, 113, 9625−9630. 53. Sasaki, D.; Kurihara, K.; Kunitake, T. Specific, multiplepoint binding of ATP and AMP to a guanidinium-functionalized monolayer. J. Am. Chem. Soc. 1991, 113, 9685−9686. 54. Shinkai, S.; Tsukagoshi, K.; Ishikawa, Y.; Kunitake, T. Molecular recognition of mono- and disaccharides by phenylboronic acids in solvent extraction and as a monolayer. J. Chem. Soc., Chem. Commun. 1991, 1039−1041. 55. Ikeura, Y.; Kurihara, K.; Kunitake, T. Molecular recognition at the air-water interface. Specific binding of nitrogen aromatics and amino acids by monolayers of long-chain derivatives of Kemp’s acid. J. Am. Chem. Soc. 1991, 113, 7342− 7350. 56. Kurihara, K.; Ohto, K.; Honda, Y.; Kunitake, T. Efficient, complementary binding of nucleic acid bases to diaminotriazinefunctionalized monolayers on water. J. Am. Chem. Soc. 1991, 113, 5077−5079. 57. Asakuma, S.; Okada, H.; Kunitake, T. Template synthesis of two-dimensional network of crosslinked acrylate polymer in a cast multibilayer film. J. Am. Chem. Soc. 1991, 113, 1749−1755. 58. Yanagi, M.; Tamamura, H.; Kurihara, K.; Kunitake, T. Binding of alkali and alkaline-earth cations to monolayers of a noncyclic ionophore. Langmuir 1991, 7, 167−172.

24. Nakashima, N.; Fukushima, H.; Kunitake, T. Large induced circular dichroism of Methyl Orange bound to chiral bilayer membranes. Its extreme sensitivity to the phase transition and the chemical structure of the membrane. Chem. Lett. 1981, 1207−1210. 25. Nakashima, N.; Ando, R.; Fukushima, H.; Kunitake, T. Controlled organization of cyanine and merocyanine dyes at the surface of synthetic bilayer membranes. J. Chem. Soc., Chem. Commun. 1982, 707−709. 26. Kunitake, T.; Ihara, H.; Okahata, Y. Phase separation and reactivity changes of phenyl ester substrate and imidazole catalyst in the dialkylammonium bilayer membrane. J. Am. Chem. Soc. 1983, 105, 6070−6078. 27. Ihara, H.; Hashiguchi, Y.; Kunitake, T. Functional fluorocarbon micelles. Phase separation and reactivity change of hydroxamate nucleophiles in mixed micelles of hydrocarbon and fluorocarbon surfactants. Chem. Lett. 1983, 733−736. 28. Kunitake, T.; Kimizuka, N.; Higashi, N.; Nakashima, N. Bilayer membranes of triple-chain ammonium amphiphiles. J. Am. Chem. Soc. 1984, 106, 1978−1983. 29. Tabushi, I.; Nishiya, T.; Shimomura, M.; Kunitake, T.; Inokuchi, H.; Yagi, T. Cytochrome c3 modified artificial liposome. Structure, electron transport, and pH gradient generation. J. Am. Chem. Soc. 1984, 106, 219−226. 30. Kunitake, T.; Shimomura, M.; Hashiguchi, Y.; Kawanaka, T. Carbazole-containing bilayer membranes and efficient energy migration. J. Chem. Soc., Chem. Commun. 1985, 833−835. 31. Nakashima, N.; Kunitake, M.; Kunitake, T.; Tone, S.; Kajiyama, T. Ordered cast films of polymerized bilayer membranes. Macromolecules 1985, 18, 1515−1516. 32. Nakashima, N.; Tsuge, A.; Kunitake, T. Selective binding of a cyanine dye at the surface of ammonium bilayer membranes. J. Chem. Soc., Chem. Commun. 1985, 41−42. 33. Kunitake, T.; Higashi, N. Bilayer membranes of triplechain, fluorocarbon amphiphiles. J. Am. Chem. Soc. 1985, 107, 692−696. 34. Ishikawa, Y.; Kunitake, T. Macroscopically oriented copper(II) chelates in cast multibilayer films. J. Am. Chem. Soc. 1986, 108, 8300−8302. 35. Kunitake, T.; Yamada, N. Helical superstructures of a bilayer-forming, single-chain ammonium amphiphile. J. Chem. Soc., Chem. Commun. 1986, 655−656. 36. Higashi, N.; Kunitake, T.; Kajiyama, T. Surface structure and oxygen permeation in mixed multibilayer films of hydrocarbon and fluorocarbon amphiphiles. Macromolecules 1986, 19, 1362−1366. 37. Kunitake, T.; Ishikawa, Y.; Shimomura, M.; Okawa, H. Ordering of metal chelates on the basis of bilayer assembly. J. Am. Chem. Soc. 1986, 108, 327−328. 38. Shimomura, M.; Kunitake, T. Fluorescence and photoisomerization of azobenzene-containing bilayer membranes. J. Am. Chem. Soc. 1987, 109, 5175−5183. 39. Higashi, N.; Kajiyama, T.; Kunitake, T.; Prass, W.; Ringsdorf, H.; Takahara, A. Cast multibilayer films from polymerizable lipids. Macromolecules 1987, 20, 29−33. 40. Takahara, A.; Higashi, N.; Kunitake, T.; Kajiyama, T. State of aggregation and surface chemical composition of composite thin films composed of poly(vinyl alcohol) and fluorocarbon amphiphile. Macromolecules 1988, 21, 2443−2446. 41. Tian, Y.; Umemura, J.; Takenaka, T.; Kunitake, T. Ultraviolet-visible absorption and resonance Raman spectra of azobenzene-containing amphiphile monolayers adsorbed at the 12237

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Preface

AUTHOR INFORMATION

Notes

Views expressed in this editorial are those of the authors and not necessarily the views of the ACS.



ACKNOWLEDGMENTS At the beginning of this Preface, the haiku in both Japanese and English was composed by Ms. Takako Dickinson.

Francoise Winnik

Professor, Editor-in-Chief of Langmuir

Marie-Paule Pileni

Professor, Guest Editor, University Pierre & Marie Curie

Kazue Kurihara

Professor, Guest Editor, Tohoku University

Atsushi Takahara

Professor, Senior Editor of Langmuir 12241

DOI: 10.1021/acs.langmuir.6b03904 Langmuir 2016, 32, 12231−12241