logo

OR SEARCH CITATIONS

My Activity
Publications
CONTENT TYPES

Figure 1Loading Img
Download Hi-Res ImageDownload to MS-PowerPointCite This:Chem. Mater. 2008, 20, 11, 3675-3687
RETURN TO ISSUEPREVArticleNEXT

Cubic Phase Formation and Interplay between Alkyl Chains and Hydrogen Bonds in 1,2-Bis(4′-n-alkoxybenzoyl)hydrazines (BABH-n)

View Author Information
Department of Chemistry, Faculty of Engineering, Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan, and Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba, Tsukuba, Ibaraki 305-8571, Japan
* To whom correspondence should be addressed. E-mail: [email protected]
†Gifu University.
‡University of Tsukuba.
Cite this: Chem. Mater. 2008, 20, 11, 3675–3687
Publication Date (Web):April 26, 2008
https://doi.org/10.1021/cm703684v
Copyright © 2008 American Chemical Society
RIGHTS & PERMISSIONS
Article Views
628
Altmetric
-
Citations
44
LEARN ABOUT THESE METRICS

Article Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.

Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.

The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated.

Read OnlinePDF (1 MB)
Get e-Alerts
Supporting Info (1)»
SUBJECTS:

Abstract

Abstract Image

The phase transitions of a homologous series of 1,2-bis(4′-n-alkoxybenzoyl)hydrazines (BABH-n, where n is the number of carbon atoms in the alkyl chain and in this investigation varies from 4 to 22) were investigated by differential scanning calorimetric (DSC), polarizing optical microscopic (POM), X-ray diffraction (XRD), and infrared (FT-IR) measurements. The formation of bicontinuous type cubic (Cub) mesophases was observed enantiotropically for n ≥ 6 and only on cooling for n = 5. The structures were examined by XRD, which revealed the presence of two types with symmetries Ia3d and Im3m, depending on n, and for n = 13, 15, and 16, phase transitions between the two Cub phases were observed. The FT-IR studies elucidated the formation of intermolecular hydrogen bonding between the C═O bond of one molecule and the NH group of another molecule, whose binding strength was temperature-dependent. The temperature dependence of the Cub lattice parameter (da/dT) varied from a large positive to a large negative value with increasing alkyl chain length n, which can be well-explained in terms of the temperature-responsive shape change of the constituent molecules. The packing structures of two Ia3d-Cub phases formed by shorter and longer alkyl chain members are compared and discussed. It is revealed that two competitive mechanisms are mainly operated on the self-organization, i.e., the preferential orientation of the long axes of the aromatic core parts parallel to each other and microsegregation between the aromatic core and alkyl chain parts of the molecules; the former mechanism is effective in the shorter chain members, whereas the latter is predominant in the longer chain members.

Supporting Information

ARTICLE SECTIONS
Jump To

Techniques and instruments, and synthetic procedures and analytical data of all compounds, including Figures S0−S16 and Tables S1 and S2 (PDF). This material is available free of charge via the Internet at http://pubs.acs.org.

Terms & Conditions

Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/page/copyright/permissions.html.

Cited By

This article is cited by 46 publications.

  1. Ryoji Ogawa, Yohei Miwa, and Shoichi Kutsumizu . FT-IR Study on Liquid Crystal Phase Transitions of Thermotropic Hydrogen-Bonded Cubic Mesogenes, 1,2-Bis(4′-n-alkoxybenzoyl)hydrazines (BABH-n) and 4′-n-Alkoxy-3′-nitrobiphenyl-4-carboxlic acid (ANBC-n): Spectroscopic Evidence for Quasibinary Picture Model. The Journal of Physical Chemistry B 2015, 119 (31) , 10131-10137. https://doi.org/10.1021/acs.jpcb.5b05498
  2. Ryo Hori, Yohei Miwa, Katsuhiro Yamamoto, and Shoichi Kutsumizu . Phase Structure and Phase Transition Mechanism for Light-Induced Ia3d Cubic Phase in 4′-n-Docosyloxy-3′-nitrobiphenyl-4-carboxlic acid/Ethyl 4-(4′-n-docosyloxyphenylazo)benzoate Binary Mixture. The Journal of Physical Chemistry B 2014, 118 (13) , 3743-3749. https://doi.org/10.1021/jp4127978
  3. Yan-Hua Cheng, Wen-Ping Chen, Zhihao Shen, Xing-He Fan, Mei-Fang Zhu, and Qi-Feng Zhou . Influences of Hydrogen Bonding and Peripheral Chain Length on Mesophase Structures of Mesogen-Jacketed Liquid Crystalline Polymers with Amide Side-Chain Linkages. Macromolecules 2011, 44 (6) , 1429-1437. https://doi.org/10.1021/ma102444t
  4. Hiroyuki Mori, Shoichi Kutsumizu, Kazuya Saito, Katsuhiro Yamamoto, Shinichi Sakurai and Koichi Sakajiri . Temperature-Jump Time-Resolved X-ray Diffraction Study of Cubic−Cubic Phase-Transition Kinetics in Thermotropic Cubic Mesogen 1,2-Bis(4′-n-alkoxybenzoyl)hydrazines (BABH-n). Langmuir 2010, 26 (14) , 11605-11608. https://doi.org/10.1021/la101553j
  5. William Dobbs, Benoît Heinrich, Cyril Bourgogne, Bertrand Donnio, Emmanuel Terazzi, Marie-Elise Bonnet, Fabrice Stock, Patrick Erbacher, Anne-Laure Bolcato-Bellemin and Laurent Douce . Mesomorphic Imidazolium Salts: New Vectors for Efficient siRNA Transfection. Journal of the American Chemical Society 2009, 131 (37) , 13338-13346. https://doi.org/10.1021/ja903028f
  6. Shoichi Kutsumizu, Kouhei Hosoyama, Makoto Yamada, Katsufumi Tanaka, Ryuichi Akiyama, Shinichi Sakurai and Eiji Funai. Smectic C to Cubic Phase Transition of 4′-n-Docosyloxy-3′-nitrobiphenyl-4-carboxylic Acid (ANBC-22) and Alternating-Current Electric Field Effect. The Journal of Physical Chemistry B 2009, 113 (3) , 640-646. https://doi.org/10.1021/jp806972x
  7. Kazumi Ozawa, Yasuhisa Yamamura, Syuma Yasuzuka, Hiroyuki Mori, Shoichi Kutsumizu and Kazuya Saito. Coexistence of Two Aggregation Modes in Exotic Liquid-Crystalline Superstructure: Systematic Maximum Entropy Analysis for Cubic Mesogen, 1,2-Bis(4′-n-alkoxybenzoyl)hydrazine [BABH(n)]. The Journal of Physical Chemistry B 2008, 112 (39) , 12179-12181. https://doi.org/10.1021/jp806481a
  8. Christian Dressel, Tino Reppe, Silvio Poppe, Marko Prehm, Huanjun Lu, Xiangbing Zeng, Goran Ungar, Carsten Tschierske. Helical Networks of π‐Conjugated Rods – A Robust Design Concept for Bicontinuous Cubic Liquid Crystalline Phases with Achiral Ia 3¯ d and Chiral I 23 Lattice. Advanced Functional Materials 2020, 23 , 2004353. https://doi.org/10.1002/adfm.202004353
  9. Akane Kawafuchi, Shoichi Kutsumizu, Yuki Kawase, Issei Tokiwa, Taro Udagawa, Yohei Miwa. Molecular design of anti-spindle-like molecules by use of siloxanyl terminals for a thermotropic bicontinuous cubic phase. Physical Chemistry Chemical Physics 2020, 22 (18) , 10132-10141. https://doi.org/10.1039/C9CP06831G
  10. Xiangbing Zeng, Goran Ungar. Spontaneously chiral cubic liquid crystal: three interpenetrating networks with a twist. Journal of Materials Chemistry C 2020, 8 (16) , 5389-5398. https://doi.org/10.1039/D0TC00447B
  11. Kazuya Saito. Importance of Molecular Crystals. 2020,,, 199-220. https://doi.org/10.1007/978-981-15-9023-8_10
  12. Kazuya Saito. Chemical Physics of Molecular Condensed Matter. 2020,,https://doi.org/10.1007/978-981-15-9023-8
  13. Kazuya Saito. Molecular Flexibility and Material Properties. 2020,,, 177-198. https://doi.org/10.1007/978-981-15-9023-8_9
  14. Kazuya Saito. Chemical Physics of Molecular Condensed Matter. 2020,,https://doi.org/10.1007/978-981-15-9023-8
  15. Yasuhisa Yamamura, Yuri Nakazawa, Shoichi Kutsumizu, Kazuya Saito. Molecular packing in two bicontinuous Ia 3̄ d gyroid phases of calamitic cubic mesogens BABH( n ): roles in structural stability and reentrant behavior. Physical Chemistry Chemical Physics 2019, 21 (42) , 23705-23712. https://doi.org/10.1039/C9CP04424H
  16. Aya Nagai, Hideaki Kondo, Yohei Miwa, Tomonori Kondo, Shoichi Kutsumizu, Yasuhisa Yamamura, Kazuya Saito. Optical Switching between Liquid-Crystalline Assemblies with Different Structural Symmetries and Molecular Orders. Bulletin of the Chemical Society of Japan 2018, 91 (11) , 1652-1659. https://doi.org/10.1246/bcsj.20180212
  17. Takeshi Sakamoto, Takafumi Ogawa, Hiroki Nada, Koji Nakatsuji, Masato Mitani, Bartolome Soberats, Ken Kawata, Masafumi Yoshio, Hiroki Tomioka, Takao Sasaki, Masahiro Kimura, Masahiro Henmi, Takashi Kato. Development of Nanostructured Water Treatment Membranes Based on Thermotropic Liquid Crystals: Molecular Design of Sub-Nanoporous Materials. Advanced Science 2018, 5 (1) , 1700405. https://doi.org/10.1002/advs.201700405
  18. Shoichi Kutsumizu, Yutaro Yamada, Tadashi Sugimoto, Nina Yamada, Taro Udagawa, Yohei Miwa. Systematic exploitation of thermotropic bicontinuous cubic phase families from 1,2-bis(aryloyl)hydrazine-based molecules. Physical Chemistry Chemical Physics 2018, 20 (12) , 7953-7961. https://doi.org/10.1039/C7CP08345A
  19. Kazuya Saito, Mafumi Hishida, Yasuhisa Yamamura. Orders Exhibited by Ensemble of Headless Spins Preferring Twisted Alignment: Phase Diagram of Extended Maier–Saupe Model on Simple Cubic Lattice. Journal of the Physical Society of Japan 2017, 86 (8) , 084602. https://doi.org/10.7566/JPSJ.86.084602
  20. Xiaohong Yao, Liliana Cseh, Xiangbing Zeng, Min Xue, Yongsong Liu, Goran Ungar. Body-centred cubic packing of spheres – the ultimate thermotropic assembly mode for highly divergent dendrons. Nanoscale Horizons 2017, 2 (1) , 43-49. https://doi.org/10.1039/C6NH00155F
  21. Kazuya Saito, Yasuhisa Yamamura, Yohei Miwa, Shoichi Kutsumizu. A structural model of the chiral “Im3m” cubic phase. Physical Chemistry Chemical Physics 2016, 18 (4) , 3280-3284. https://doi.org/10.1039/C5CP06658A
  22. Shoichi Kutsumizu, Issei Tokiwa, Akane Kawafuchi, Yohei Miwa, Yasuhisa Yamamura, Kazuya Saito. Stabilization of the bicontinuous cubic phase in siloxane-terminated mesogens, 1,2-bis[4′-(n-(oligodimethylsiloxyl)alkoxy)benzoyl]hydrazine. Physical Chemistry Chemical Physics 2016, 18 (13) , 9013-9020. https://doi.org/10.1039/C6CP00622A
  23. Shoichi Kutsumizu, Suguru Miisako, Yohei Miwa, Makoto Kitagawa, Yasuhisa Yamamura, Kazuya Saito. Mirror symmetry breaking by mixing of equimolar amounts of two gyroid phase-forming achiral molecules. Physical Chemistry Chemical Physics 2016, 18 (26) , 17341-17344. https://doi.org/10.1039/C6CP02954J
  24. Mika Umeyama, Shuhei Fujimura, Yasuhisa Yamamura, Mafumi Hishida, Shoichi Kutsumizu, Kazuya Saito. Liquid-crystallinity of cubic phase of BABH(6) through thermal analysis of solid–solid phase transitions. Thermochimica Acta 2014, 590 , 160-164. https://doi.org/10.1016/j.tca.2014.06.024
  25. Yoji Maeda, Yasuhisa Yamamura, Shoichi Kutsumizu, Kazuya Saito. Phase behaviour of a thermotropic cubic mesogen of 1,2-bis(4′- n -hexyloxybenzoyl)hydrazine under pressure. Liquid Crystals 2014, 41 (5) , 731-737. https://doi.org/10.1080/02678292.2013.878963
  26. J. M. Marković, N. P. Trišović, T. Tóth-Katona, M. K. Milčić, A. D. Marinković, C. Zhang, A. J. Jákli, K. Fodor-Csorba. A structure–property relationship study of bent-core mesogens with pyridine as the central unit. New J. Chem. 2014, 38 (4) , 1751-1760. https://doi.org/10.1039/C3NJ01430D
  27. Yoji Maeda, Shoichi Kutsumizu, Shinichi Sakurai. The pressure effect on thermotropic cubic phases of 1,2-bis(4′-n-alkoxybenzoyl)hydrazines. Physical Chemistry Chemical Physics 2014, 16 (9) , 4329. https://doi.org/10.1039/c3cp54471k
  28. Kazuya Saito, Takahito Miyazawa, Akio Fujiwara, Mafumi Hishida, Hideki Saitoh, Maria Massalska-Arodź, Yasuhisa Yamamura. Reassessment of structure of smectic phases: Nano-segregation in smectic E phase in 4- n -alkyl-4′-isothiocyanato-1,1′-biphenyls. The Journal of Chemical Physics 2013, 139 (11) , 114902. https://doi.org/10.1063/1.4821162
  29. Takuya Adachi, Hideki Saitoh, Yasuhisa Yamamura, Mafumi Hishida, Mao Ueda, Shunji Ito, Kazuya Saito. Universality of Molten State of Alkyl Chain in Liquid-Crystalline Mesophases: Smectic E Phase of 6-Alkyl-2-phenylazulene. Bulletin of the Chemical Society of Japan 2013, 86 (9) , 1022-1027. https://doi.org/10.1246/bcsj.20130122
  30. Shoichi Kutsumizu. Recent Progress in the Synthesis and Structural Clarification of Thermotropic Cubic Phases. Israel Journal of Chemistry 2012, 52 (10) , 844-853. https://doi.org/10.1002/ijch.201200032
  31. Yuri Nakazawa, Yasuhisa Yamamura, Shoichi Kutsumizu, Kazuya Saito. Molecular Mechanism Responsible for Reentrance to Ia3d Gyroid Phase in Cubic Mesogen BABH( n ). Journal of the Physical Society of Japan 2012, 81 (9) , 094601. https://doi.org/10.1143/JPSJ.81.094601
  32. Huei-Yun Lin, Hsiu-Ming Kuo, Shao-Gang Wen, Hwo-Shuenn Sheu, Gene-Hsiang Lee, Chung K. Lai. Hydrogen-bond-assisted supramolecular 1-D tape-like structures of mesogenic bis-pyrazoles. Tetrahedron 2012, 68 (31) , 6231-6239. https://doi.org/10.1016/j.tet.2012.05.060
  33. Ryo Hori, Daisuke Furukawa, Katsuhiro Yamamoto, Shoichi Kutsumizu. Light-Driven Phase Transition in a Cubic-Phase-Forming Binary System Composed of 4′- n -Docosyloxy-3′-nitrobiphenyl-4-carboxylic Acid and an Azobenzene Derivative. Chemistry - A European Journal 2012, 18 (24) , 7346-7350. https://doi.org/10.1002/chem.201200810
  34. Yoji Maeda, Shoichi Kutsumizu, Shinichi Sakurai. Pressure-induced cubic–cubic transition in 1,2-bis(4'- n -tetradecyloxybenzoyl)hydrazine. Liquid Crystals 2012, 39 (4) , 451-455. https://doi.org/10.1080/02678292.2011.653414
  35. Suguru Miisako, Shoichi Kutsumizu, Koichi Sakajiri. A partially crosslinked bicontinuous cubic phase exhibiting a temperature range of more than 100 °C. Chemical Communications 2012, 48 (16) , 2225. https://doi.org/10.1039/c2cc16411f
  36. Li Wang, Xiao-Jun Liu, Ping Huang, Qing-Ping Gong, Yong-Hong Li, Bi-Qin Wang, Ke-Qing Zhao. A New Way to Access Chiral Liquid Crystals: Organocatalyst-Mediated Synthesis of Chiral Rod-Like Liquid Crystals. Molecular Crystals and Liquid Crystals 2011, 541 (1) , 53/[291]-59/[297]. https://doi.org/10.1080/15421406.2011.570138
  37. Makoto Yoneya. Toward rational design of complex nanostructured liquid crystals. The Chemical Record 2011, 11 (2) , 66-76. https://doi.org/10.1002/tcr.201000025
  38. Jean-Moïse Suisse, Hiroyuki Mori, Hirosato Monobe, Shoichi Kutsumizu, Yo Shimizu. Charged carrier mobility in the cubic (Ia3d) mesophase of 1,2-bis(4′-n-nonyloxybenzoyl)hydrazine (BABH-9). Soft Matter 2011, 7 (23) , 11086. https://doi.org/10.1039/c1sm06224g
  39. Wojciech Pisula, Xinliang Feng, Klaus Müllen. Tuning the Columnar Organization of Discotic Polycyclic Aromatic Hydrocarbons. Advanced Materials 2010, 22 (33) , 3634-3649. https://doi.org/10.1002/adma.201000585
  40. Akira Mori, Emi Yamamoto, Kanji Kubo, Seiji Ujiie, Ute Baumeister, Carsten Tschierske. Bicontinuous cubic phase with the Pn3m space group formed by N,N,N -tris(5-alkoxytroponyl)-1,5,9-triazacyclododecanes. Liquid Crystals 2010, 37 (8) , 1059-1065. https://doi.org/10.1080/02678292.2010.482677
  41. Sih-Yeh Li, Chun-Jung Chen, Po-Yuan Lo, Hwo-Shuenn Sheu, Gene-Hsiang Lee, Chung K. Lai. H-Bonded metallomesogens derived from salicyladiminates. Tetrahedron 2010, 66 (32) , 6101-6112. https://doi.org/10.1016/j.tet.2010.06.002
  42. Yoji Maeda, Hiroyuki Mori, Shoichi Kutsumizu. Morphological phase behaviour of a homologous series of thermotropic cubic mesogens under pressure. Liquid Crystals 2010, 37 (4) , 463-473. https://doi.org/10.1080/02678291003653658
  43. Ming-Shou Ho, Chain-Shu Hsu. Synthesis and self-assembled nanostructures of novel chiral amphiphilic liquid crystals containing β- d -galactopyranoside end-groups. Liquid Crystals 2010, 37 (3) , 293-301. https://doi.org/10.1080/02678291003611342
  44. Yoji Maeda, Hiroyuki Mori, Shoichi Kutsumizu. Inversion of the phase sequence between the cubic and smectic C phases under pressure. Liquid Crystals 2009, 36 (3) , 217-223. https://doi.org/10.1080/02678290902814692
  45. Kazuya Saito, Tadahiro Nakamoto, Michio Sorai, Haruhiko Yao, Kenji Ema, Kunio Takekoshi, Shoichi Kutsumizu. Thermodynamic symptom of coexistence of two aggregation modes in the Im3m cubic phase formed in thermotropic mesogen, ANBC(n). Chemical Physics Letters 2009, 469 (1-3) , 157-160. https://doi.org/10.1016/j.cplett.2008.12.072
  46. Kazuya Saito, Yasuhisa Yamamura, Shoichi Kutsumizu. Possible Formation of Multicontinuous Structures by Rodlike Particles. Journal of the Physical Society of Japan 2008, 77 (9) , 093601. https://doi.org/10.1143/JPSJ.77.093601

Pair your accounts.

Export articles to Mendeley

Get article recommendations from ACS based on references in your Mendeley library.

Pair your accounts.

Export articles to Mendeley

Get article recommendations from ACS based on references in your Mendeley library.

You’ve supercharged your research process with ACS and Mendeley!

STEP 1:
Click to create an ACS ID

Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

OOPS

You have to login with your ACS ID befor you can login with your Mendeley account.

MENDELEY PAIRING EXPIRED
Your Mendeley pairing has expired. Please reconnect

This website uses cookies to improve your user experience. By continuing to use the site, you are accepting our use of cookies. Read the ACS privacy policy.

CONTINUE