Supramolecular Rod: New Molecular Design Consept of MFMS

• Project/Area Number: 25620050
• Research Category: Grant-in-Aid for Challenging Exploratory Research
• Allocation Type: Multi-year Fund
• Research Field: Functional solid state chemistry
• Research Institution: Hokkaido University
• Principal Investigator: SUZUKI Takanori 北海道大学, 理学(系)研究科(研究院), 教授 (70202132)
• Project Period (FY): 2013-04-01 – 2015-03-31
• Project Status: Completed (Fiscal Year 2014)
• Budget Amount: ¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000); Fiscal Year 2014: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000); Fiscal Year 2013: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
• Keywords: 酸化還元 / アトムエコノミー / 機能性分子 / 多重機能 / 応答性分子

Outline of Final Research Achievements

The acronym "MFMS" represents the molecular design concept of "maximum function on the minimum skeleton", which has been increasing in importance, especially for the design of advanced response systems. When a modular design is applied to multi-output-multi-input response systems, the multiple functional moieties have to be connected, resulting in a larger molecular size.
On the other hand, under the "MFMS" concept, the potential functions of molecules are educed by slight structural modification of a preexisting moiety to add another functionality. The "MFMS" is an atom-economical approach for the future development of highly functional materials. In this study, two kinds of multi-output molecular response systems were developed based on our electrochromic dyrex (dynamic redox) system.

Research Products

• [Journal Article] Reversible Interconversion between 11,11,12,12-Tetraaryl-1,4-diaza/-1,4,5,8-tetraazaanthraquinodimethanes and Their Cationic Species: Electrochromic and Halochromic Responses (2015)
  • Author(s): Takanori Suzuki, Yuu Umezawa, Yuto Sakano, Hitomi Tamaoki, Ryo Katoono, and Kenshu Fujiwara
  • Journal Title: Chemistry Letters Volume: 44 Issue: 7 Pages: 905-907
  • DOI: 10.1246/cl.150251
  • NAID: 130005085140
  • Peer Reviewed
• [Journal Article] New Insights into the Hexaphenylethane Riddle: Formation of an α,o-Dimer (2015)
  • Author(s): Y. Uchimura, T. Takeda, R. Katoono, K. Fujiwara, and T. Suzuki
  • Journal Title: Angewandte Chemie International Edition Volume: 54 Issue: 13 Pages: 4010-4013
  • DOI: 10.1002/anie.201500122
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Bis(10-methylacridinium)s as a Versatile Platform for Redox-Active Functionalized Dyes and Novel Structure (2015)
  • Author(s): T. Suzuki, T. Takeda, E. Ohta, K. Wada, R. Katoono, H. Kawai, K. Fujiwara
  • Journal Title: Chem. Rec. Volume: 15 Pages: 280-294
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Bis(diarylethenyl)thiophene, -bithiophene, and -terthiophene: A New Series of Violene-Cyanine Hybrid-Type Electron Donors (2015)
  • Author(s): Yusuke Ishigaki, Hidetsohi Kawai, Ryo Katoono, Kenshu Fujiwara, Takanori Suzuki
  • Journal Title: Heterocycles Volume: 90 Issue: 1 Pages: 136-143
  • DOI: 10.3987/com-14-s(k)33
  • Peer Reviewed
• [Journal Article] Three-Way Output Molecular Response System based on Tetrakis(3,4-dialkoxyphenyl)-3,4-dihydro[5]helicenes: Perturbation of Properties by Long Alkyl Chains (2015)
  • Author(s): Yusuke Ishigaki, Satoshige Yoshida, Hidetoshi Kawai, Ryo Katoono, Kenshu Fujiwara, Takanori Fukushima, Takanori Suzuki
  • Journal Title: Heterocycles Volume: 90 Issue: 1 Pages: 126-135
  • DOI: 10.3987/com-14-s(k)31
  • Peer Reviewed
• [Journal Article] Wurster's Blue-type Cation Radicals Framed in a 5,10-Dihydrobenzo[a]indolo[2,3-c]carbazole (BIC) Skeleton: Dual Electrochromism with Drastic Changes in UV-Vis-NIR and Fluorescence, (2014)
  • Author(s): T. Suzuki, Y. Sakano, Y. Tokimizu, Y. Miura, R. Katoono, K. Fujiwara, N. Yoshioka, N. Fujii, H. Ohno,
  • Journal Title: Chem. Asian J Volume: 9 Pages: 1841-1846
  • Peer Reviewed
• [Journal Article] Preparation, Redox Properties, and perties, and X-ray Strucures of Electrochromic 11,11,12,12- Tetraarylanthraquinodimethane and Its Bianthraquinodimethane Analogue: Drastic Geometrical Changes upon Interconversion with the Dicationic Dyes (2014)
  • Author(s): Sakano, Y.; Katoono, R.; Fujiwara, K.; Suzuki, T
  • Journal Title: Chem. Lett Volume: (in press) Issue: 7 Pages: 1143-1145
  • DOI: 10.1246/cl.140393
  • NAID: 130004868285
  • Peer Reviewed / Open Access
• [Journal Article] Oxidative Protonolysis of the Expanded Central C-C Bond in a Di(spiroacridan)-type Hexaphenylethane Derivative Accompanied by UV-vis, FL, and CD Spectral Changes (2014)
  • Author(s): Suzuki, T.; Kuroda, Y.; Wada, K.; Sakano, Y.; Katoono, R.; Fujiwara, K.; Kakiuchi, F.; Fukushima, T
  • Journal Title: Chem. Lett Volume: (in press) Issue: 6 Pages: 887-889
  • DOI: 10.1246/cl.140192
  • NAID: 130004868213
  • Peer Reviewed
• [Journal Article] Electrochiroptical Response in Aqueous Media: 9.10-Dihydrophenanthrene-9,10-diyl Dications with Michlar's Hydrol Blue Chromophores Attached with Oligoethylene Glycol Units, (2014)
  • Author(s): T. Suzuki, K. Hanada, R. Katoono, Y. Ishigaki, S. Higasa, H. Higuchi, H. Kikuchi, K. Fujiwara, H. Yamada, T. Fukushima,
  • Journal Title: Chem. Lett. Volume: 印刷中 Issue: 7 Pages: 982-984
  • DOI: 10.1246/cl.140163
  • NAID: 130004868230
  • Peer Reviewed
• [Journal Article] Cyanoazulene-based Multi-stage Redox Systems Prepared from Vinylcyclopropane-carbonitrile and Cyclopentenone via Divinylcyclopropane-rearrangement Approach (2014)
  • Author(s): Keiji Tanino, Takumasa Yamada, Fumihiko Yoshimura, and Takanori Suzuki
  • Journal Title: Chemistry Letters Volume: 43 Issue: 5 Pages: 607-609
  • DOI: 10.1246/cl.131149
  • NAID: 130004868100
  • Peer Reviewed
• [Journal Article] Preparation and structure of acenaphthylene-1,2-diyldi(9-acridine) with a long C=C bond (2014)
  • Author(s): Takashi Takeda, Yasuto Uchimura, Hidetoshi Kawai, Ryo Katoono, Kenshu Fujiwara, Takanori Suzuki
  • Journal Title: Chemical Communications Volume: 50 Issue: 30 Pages: 3924-3927
  • DOI: 10.1039/c3cc49573f
  • Peer Reviewed / Open Access
• [Journal Article] Expandability of ultralong C-C bond : Largely different C_1-C_2 bond length determined by low-temperature X-ray structural analyses on pseudopolymorphs of 1,1-Bis(4-fluorophenyl)-2,2-bis(4-methoxyp henyl)pyracene (2014)
  • Author(s): Takanori Suzuki, Yasuto Uchimura, Takashi Takeda, Hidetoshi Kawai, Ryo Katoono, Kenshu Fujiwara, Kei Murakoshi, Takanori Fukushima, Aiichiro Nagaki, Junichi Yoshida
  • Journal Title: Chemistry Letters Volume: 43 Issue: 1 Pages: 86-88
  • DOI: 10.1246/cl.130872
  • NAID: 130004427101
  • Peer Reviewed / Open Access
• [Journal Article] Electrochromic and unique chiroptical properties of helically deformed tetraarylquinodimethanes generated from less hindered dicationic precursors upon reduction (2014)
  • Author(s): Suzuki, T.; Sakano, Y.; Iwai, T.; Iwashita, S.; Miura, Y.; Katoono, R.; Kawai, H.; Fujiwara, K.; Tsuji, Y.; Fukushima, T
  • Journal Title: Pure Appl. Chem Volume: (in press) Issue: 4 Pages: 507-516
  • DOI: 10.1515/pac-2013-1003
  • Peer Reviewed
• [Journal Article] Chiral Memory Units Based on Dynamic Redox Systems with a Dibenzoxepinone Skeleton: Drastic Change in Racemization Barrier and Electrochemical Bistability (2014)
  • Author(s): K. Wada, Y. Chiba, T. Takeda, H. Kawai, R. Katoono, K. Fujiwara, T. Suzuki
  • Journal Title: Heterocycles Volume: 88 Pages: 945-962
  • Peer Reviewed
• [Journal Article] Chiral Memory Units Based on Dynamic Redox Systems with a Dibenzoxepinone Skeleton (2014)
  • Author(s): K. Wada, Y. Chiba, T. Takeda, H. Kawai, R. Katoono, K. Fujiwara, T. Suzuki
  • Journal Title: Heterocycles Volume: 88(2), Pages: 945-952
  • Peer Reviewed
• [Journal Article] Expandability of Ultralong C-C Bond: Largely Different C1-C2 Bond Length Determined by Low-temperature X-ray Analyses on Pseudopolymorphs of 1,1-Bis(4-fluorophenyl)-2,2-bis(4-methoxyphenyl)pyracene, (2014)
  • Author(s): T. Suzuki, Y. Uchimura, F. Nagasawa, T. Takeda, H. Kawai, R. Katoono, K. Fujiwara, K. Murakoshi, T. Fukushima, A. Nagaki, J. Yoshida
  • Journal Title: Chem. Lett Volume: 43(1) Pages: 85-88
  • Peer Reviewed
• [Journal Article] Cyanoazulene-based Muti-stage Redox Systems Prepared from Vinylcyclopropanecarbonitrile and Cyclopentenone via Divinylcyclopropane-rearrangement Approach (2014)
  • Author(s): K. Tanino, Y. Yamada, F. Yoshimura, T. Suzuki
  • Journal Title: Chem. Lett. Volume: 43（５） Pages: 607-609
  • Peer Reviewed
• [Journal Article] Complexation-induced inversion of helicity by an organic guest in a dynamic molecular propeller based on a tristerephtalamide host with a two-layer structure (2014)
  • Author(s): R. Katoono, K. Fujiwara, T. Suzuki,
  • Journal Title: Chem. Commun. Volume: 50 Pages: 5438-5440
  • Peer Reviewed
• [Journal Article] 7,7,8,8-Tetraaryl-o-quinodimethane Stabilized by Dibenzo-annulation: A Helical pi-Electron System that Exhibits Electrochromic and Unique Chiroptical Properties, (2013)
  • Author(s): T. Suzuki, Y. Sakano, T. Iwai, S. Iwashita, Y. Miura, R. Katoono, H. Kawai, K. Fujiwara, Y. Tsuji, T. Fukushima,
  • Journal Title: Chem. Eur. J. Volume: 19(1) Pages: 117-123
  • Peer Reviewed
• [Journal Article] Hydrindacene-based acetylenic macrocycles with horizontally and vertically ordered functionality arrays, (2013)
  • Author(s): H. Kawai, T. Utamura, E. Motoi, T. Takahashi, H. Sugino, M. Tamura, M. Ohkita, K. Fujiwara, T. Saito, T. Tsuji, T. Suzuki,
  • Journal Title: Chem. Eur. J. Volume: 19(14) Pages: 4513-4524
  • Peer Reviewed
• [Journal Article] Redox switching of conjugation length using 9,9,10,10-tetraaryl-9,10-dihydrophennanthene as an ON/OFF unit: Preparation, X-ray structure, and redox properties of perfluorobiphenyl derivative and its SNAr reactions to pi-extended analogues, (2013)
  • Author(s): T. Suzuki, H. Tamaoki, R. Katoono, K. Fujiwara, J. Ichikawa, T. Fukushima,
  • Journal Title: Chem. Lett. Volume: 42(7) Pages: 703-705
  • Peer Reviewed
• [Journal Article] Oxidative conversion of tetraaryldihydrodibenzothiepins into elemental sulfur and stable cationic dyes accompanied by dual UV-Vis and CD spectral changes (2013)
  • Author(s): T. Suzuki, T. Kuroda, H. Tamaoki, S. Higasa, R. Katoono, K. Fujiwara, T. Fukushima, H. Yamada,
  • Journal Title: Chem. Lett. Volume: 42(7) Pages: 706-708
  • NAID: 10031183266
  • Peer Reviewed
• [Journal Article] 5,10-Dihydrobenzo[a]indolo[2,3-c]carbazole: A highly fluorescent disk-shaped electron donor exhibiting dual UV-Vis-NIR and fluorescence spectral changes upon electrolysis (2013)
  • Author(s): T. Suzuki, Y. Tokimizu, Y. Sakano, R. Katoono, K. Fujiwara, S. Naoe, N. Fujii, H. Ohno,
  • Journal Title: Chem. Lett Volume: 42(9） Pages: 1001-1003
  • NAID: 10031194320
  • Peer Reviewed
• [Journal Article] Preparation, properties, and X-ray structures of bis(10-methyl-9- methyleneacridan)-type electron donors with a thiophene/bithiophene/terthiophene skeleton: Redox switching of thiophene-thienoquinoid structure accompanied by UV-Vis-NIR electrochromic response (2013)
  • Author(s): T. Suzuki, Y. Hoshiyama, K. Wada, Y. Ishigaki, Y. Miura, H. Kawai, R. Katoono, K. Fujiwara, T. Fukushima,
  • Journal Title: Chem. Lett Volume: 42(9） Pages: 1004-1006
  • Peer Reviewed
• [Journal Article] C3-symmetric chrioptical molecular propeller based on hexakis(phenylethynyl)benzene with a threefold terephthalamide: stereospecific propeller generation through the cooperative transmission of point chiralities on the host and guest upon complexation (2013)
  • Author(s): R. Katoono, H. Kawai, M. Ohkita, K. Fujiwara, T. Suzuki,
  • Journal Title: Chem. Commun. Volume: 49(88) Pages: 10352-10354
  • Peer Reviewed
• [Journal Article] Time-integrated one-pot synthesis, X-ray structure, and redox properties of electrochromic 1,3-diarylisobenzofurans (2013)
  • Author(s): T. Hamura, R. Nakayama, K. Hanada, Y. Sakano, R. Katoono, K. Fujiwara, T. Suzuki,
  • Journal Title: Chem. Lett Volume: 42(10) Pages: 1244-1246
  • NAID: 10031201325
  • Peer Reviewed
• [Journal Article] Geometrical Remote Steric Effects in 4,5-Disubsitituted-9,10-dihydrophenanthrenes: Expansion of Prestrained C9-C10 Bond in Di(spiroacridan) Derivatives (2013)
  • Author(s): K. Wada, T. Takeda, H. Kawai, R. Katoono, K. Fujiwara, T. Suzuki
  • Journal Title: Chem. Lett Volume: 42(10) Pages: 1194-1196
  • Peer Reviewed
• [Journal Article] Hexaphenylethanes with an Ultralong C-C Bond: Expandability of the C-C Bond in Highly Strained Tetraarylopyracenes, (2013)
  • Author(s): T. Takada, Y. Uchimura, H. Kawai, R. Katoono, K. Fujiwara, T. Suzuki,
  • Journal Title: Chem. Lett .(highlight reviw) Volume: 42(9) Pages: 954-962
  • Peer Reviewed
• [Presentation] ビス（１０-メチルアクリジニウム）型色素の化学： 多重出力型エレクトロクロミズムから世界記録を持つ特異な構造まで (2014)
  • Author(s): 鈴木孝紀
  • Organizer: 2014年電気化学秋季大会
  • Place of Presentation: 北海道大学(札幌市）
  • Year and Date: 2014-09-27 – 2014-09-28
  • Invited
• [Presentation] Can Packing Change the Bond Lengh of Ultralong C-C Bonds? (2014)
  • Author(s): Takanori Suzuki, Yasuto Uchimura, Takashi Takeda, Ryo Katoono, Hidetoshi Kawai, Kenshu Fujiwara
  • Organizer: CGOM11 (Crystal Growth of Organic Materials)
  • Place of Presentation: 奈良県新公会堂(奈良）
  • Year and Date: 2014-06-17 – 2014-06-20
  • Invited
• [Presentation] Electrochromic and Unique Chiroptical Properties of Helically Deformed Tetraarylquinodimethanes (2013)
  • Author(s): T. Suzuki
  • Organizer: 15th International Symposium on Novel Aromatic Compounds
  • Place of Presentation: Howard Civil Service International House (Taiwan)
  • Invited