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Solid-state thermo- and photochromism in N,N′-bis(5-X-salicylidene) diamines (X = H, Br)

Bibliographic reference Safin, Damir ; Robeyns, Koen ; Garcia, Yann. Solid-state thermo- and photochromism in N,N′-bis(5-X-salicylidene) diamines (X = H, Br). In: RSC Advances, Vol. 2, no. 30, p. 11379-11388 (2012)
Permanent URL http://hdl.handle.net/2078.1/125591
  1. Irie M., Photochromism:  Memories and SwitchesIntroduction, 10.1021/cr980068l
  2. Irie Masahiro, Photochromism of diarylethene single molecules and single crystals, 10.1039/c0pp00251h
  3. Irie Masahiro, Morimoto Masakazu, Photochromic diarylethene molecules and crystals, 10.1351/pac-con-08-09-26
  4. Feringa Ben L., Jager Wolter F., de Lange Ben, Organic materials for reversible optical data storage, 10.1016/s0040-4020(01)81913-x
  5. Kawata Satoshi, Kawata Yoshimasa, Three-Dimensional Optical Data Storage Using Photochromic Materials, 10.1021/cr980073p
  6. Feringa Ben L., In Control of Motion:  From Molecular Switches to Molecular Motors†, 10.1021/ar0001721
  7. Yao J. N., Hashimoto K., Fujishima A., Photochromism induced in an electrolytically pretreated Mo03 thin film by visible light, 10.1038/355624a0
  8. Bechinger Clemens, Ferrere Suzanne, Zaban Arie, Sprague Julian, Gregg Brian A., Photoelectrochromic windows and displays, 10.1038/383608a0
  9. Bren Vladimir A., Dubonosov Alexander D., Minkin Vladimir I., Gribanova Tatyana N., Rybalkin Vladimir P., Shepelenko Evgenii N., Tsukanov Alexey V., Borisenko Roman N., Photochromic Cation Sensors, 10.1080/15421400590946956
  10. Nakatani Keitaro, Delaire Jacques A., Reversible Photoswitching of Second-Order Nonlinear Optical Properties in an Organic Photochromic Crystal, 10.1021/cm970369w
  11. Delaire Jacques A., Nakatani Keitaro, Linear and Nonlinear Optical Properties of Photochromic Molecules and Materials, 10.1021/cr980078m
  12. Cohen M. D., Schmidt G. M. J., PHOTOCHROMY AND THERMOCHROMY OF ANILS1, 10.1021/j100818a030
  13. Cohen M. D., Schmidt G. M. J., Flavian S., 388. Topochemistry. Part VI. Experiments on photochromy and thermochromy of crystalline anils of salicylaldehydes, 10.1039/jr9640002041
  14. Cohen M. D., Hirshberg Y., Schmidt G. M. J., 389. Topochemistry. Part VII. The photoactivity of anils of salicylaldehydes in rigid solutions, 10.1039/jr9640002051
  15. Cohen M. D., Hirshberg Y., Schmidt G. M. J., 390. Topochemistry. Part VIII. The effect of solvent, temperature, and light on the structure of anils of hydroxynaphthaldehydes, 10.1039/jr9640002060
  16. Bregman Judith, Leiserowitz L., Schmidt G. M. J., 391. Topochemistry. Part IX. The crystal and molecular structures of N-5-chlorosalicylideneaniline near 90 and 300°K, 10.1039/jr9640002068
  17. Cohen M. D., Flavian S., Topochemistry. Part XXIV. The luminescence properties of N-salicylideneaniline and related anils in solution, 10.1039/j29670000317
  18. Cohen M. D., Flavian S., Topochemistry. Part XXV. The absorption spectra of some N-salicylideneanilines and related anils in solution, 10.1039/j29670000321
  19. Cohen M. D., Flavian S., Leiserowitz L., Topochemistry. Part XXVI. The absorption spectra of some thermochromic N-salicylideneanilines and hydroxynaphthylideneanilines in the crystal, 10.1039/j29670000329
  20. Cohen M. D., Flavian S., Topochemistry. Part XXVII. The luminescence of crystalline N-salicylideneanilines and related anils, 10.1039/j29670000334
  21. Cohen M. D., Topochemistry. Part XXVIII. The system: 4-chloro-N-salicylideneaniline—4-bromo-N-salicylideneaniline, 10.1039/j29680000373
  22. Mikami, J. Phys. Chem. B, 33, 579 (2004)
  23. Hadjoudis Eugene, Photochromic and thermochromic anils, 10.1007/bf01004014
  24. Senier Alfred, Shepheard Frederick George, LIV.—Salicylidene-m-toluidine, a new phototropic compound; salicylideneamines: salicylamides, 10.1039/ct9099500441
  25. Senier Alfred, Shepheard Frederick George, CCXIV.—Studies in phototropy and thermotropy. Part I. Arylidene- and naphthylidene-amines, 10.1039/ct9099501943
  26. Senier Alfred, Shepheard Frederick George, Clarke Rosalind, CCVII.—Studies in phototropy and thermotropy. Part III. Arylideneamines, 10.1039/ct9120101950
  27. Senier Alfred, Clarke Rosalind, CLXXIX.—Studies in phototropy and thermotropy. Part IV. o-Nitrobenzylidenearylamines and their photoisomeric change, 10.1039/ct9140501917
  28. Senier Alfred, Forster Robert Benjamin, CCXXX.—Studies in phototropy and thermotropy. Part V. Polymorphic 4-hydroxybenzylideneamines produced by trituration and by the influence of sunlight, 10.1039/ct9140502462
  29. Kumar, J. Sci. Ind. Res., 68, 181 (2009)
  30. Robert François, Tinant Bernard, Clérac Rodolphe, Jacquemin Pierre-Loïc, Garcia Yann, Self assembly of asymmetric tetranuclear Cu(II) [2×2] grid-like complexes and of a dinuclear Ni(II) complex from pyridyl-phenol Schiff base ligands, 10.1016/j.poly.2010.06.017
  31. Fujiwara Toshikatsu, Harada Jun, Ogawa Keiichiro, Solid-State Thermochromism Studied by Variable-Temperature Diffuse Reflectance Spectroscopy. A New Perspective on the Chromism of Salicylideneanilines, 10.1021/jp037438g
  32. Hadjoudis, Chem. Soc. Rev., 33, 579 (2004)
  33. Amimoto Kiichi, Kawato Toshio, Photochromism of organic compounds in the crystal state, 10.1016/j.jphotochemrev.2005.12.002
  34. Haneda Tsuyoshi, Kawano Masaki, Kojima Takahiro, Fujita Makoto, Thermo-to-Photo-Switching of the Chromic Behavior of Salicylideneanilines by Inclusion in a Porous Coordination Network, 10.1002/anie.200700999
  35. Inokuma Yasuhide, Kawano Masaki, Fujita Makoto, Crystalline molecular flasks, 10.1038/nchem.1031
  36. Hadjoudis E., Vittorakis M., Moustakali-Mavridis I., Photochromism and thermochromism of schiff bases in the solid state and in rigid glasses, 10.1016/s0040-4020(01)90255-8
  37. Robert François, Naik Anil D., Tinant Bernard, Robiette Raphaël, Garcia Yann, Insights into the Origin of Solid-State Photochromism and Thermochromism ofN-Salicylideneanils: The Intriguing Case of Aminopyridines, 10.1002/chem.200801932
  38. Robert François, Naik Anil D., Hidara Florence, Tinant Bernard, Robiette Raphaël, Wouters Johan, Garcia Yann, Engineering Solid-State Molecular Switches:N-Salicylidene N-Heterocycle Derivatives, 10.1002/ejoc.200901175
  39. Robert François, Jacquemin Pierre-Loïc, Tinant Bernard, Garcia Yann, Trans-keto* form detection in non photochromic N-salicylidene aminomethylpyridines, 10.1039/c2ce00006g
  40. Safin Damir A., Robeyns Koen, Garcia Yann, Crown ether-containing N-salicylidene aniline derivatives: synthesis, characterization and optical properties, 10.1039/c2ce25600b
  41. Chatziefthimiou Spyros D., Lazarou Yannis G., Hadjoudis Eugene, Dziembowska Tereza, Mavridis Irene M., Keto Forms of Salicylaldehyde Schiff Bases:  Structural and Theoretical Aspects, 10.1021/jp064110p
  42. Hadjoudis Eugene, Chatziefthimiou Spyros, Mavridis Irene, Anils: Photochromism by H-transfer, 10.2174/138527209787314797
  43. Hoshino Naomi, Inabe Tamotsu, Mitani Tadaoki, Maruyama Yusei, Structure and Optical Properties of a Thermochromic Schiff Base. Thermally Induced Intramolecular Proton Transfer in theN,N′-Bis(salicylidene)-p-phenylenediamine Crystals, 10.1246/bcsj.61.4207
  44. Inabe Tamotsu, Hoshino Naomi, Mitani Tadaoki, Maruyama Yusei, Structure and Optical Properties of a Thermochromic Schiff Base. Low-Temperature Structural Studies of theN,N′-Disalicylidene-p-phenylenediamine andN,N′-Disalicylidene-1,6-pyrenediamine Crystals, 10.1246/bcsj.62.2245
  45. Ito Eisuke, Oji Hiroshi, Araki Tohru, Oichi Kazuyoshi, Ishii Hisao, Ouchi Yukio, Ohta Toshiaki, Kosugi Nobuhiro, Maruyama Yusei, Naito Toshio, Inabe Tamotsu, Seki Kazuhiko, Soft X-ray Absorption and X-ray Photoelectron Spectroscopic Study of Tautomerism in Intramolecular Hydrogen Bonds ofN-Salicylideneaniline Derivatives, 10.1021/ja9641362
  46. Sekikawa Taro, Kobayashi Takayoshi, Inabe Tamotsu, Femtosecond Fluorescence Study of Proton-Transfer Process in Thermochromic Crystalline Salicylideneanilines, 10.1021/jp9715888
  47. Ziółek Marcin, Kubicki Jacek, Maciejewski Andrzej, Naskrȩcki Ryszard, Grabowska Anna, Enol-keto tautomerism of aromatic photochromic Schiff base N,N′-bis(salicylidene)-p-phenylenediamine: Ground state equilibrium and excited state deactivation studied by solvatochromic measurements on ultrafast time scale, 10.1063/1.2179800
  48. Ziółek Marcin, Burdziński Gotard, Karolczak Jerzy, Influence of Intermolecular Hydrogen Bonding on the Photochromic Cycle of the Aromatic Schiff BaseN,N′-Bis(salicylidene)-p-phenylenediamine in Solution, 10.1021/jp803850n
  49. Yıldız M., Kılıç Z., Hökelek T., Intramolecular hydrogen bonding and tautomerism in Schiff bases. Part I. Structure of 1,8-di[N-2-oxyphenyl-salicylidene]-3,6-dioxaoctane, 10.1016/s0022-2860(97)00291-3
  50. Popović Z., Roje V., Pavlović G., Matković-Čalogović D., Giester G., The first example of coexistence of the ketoamino–enolimino forms of diamine Schiff base naphthaldimine parts: the crystal and molecular structure of N , N ′-bis(1-naphthaldimine)- o -phenylenediamine chloroform (1/1) solvate at 200 K, 10.1016/s0022-2860(01)00574-9
  51. Hadjoudis Eugene, Rontoyianni Aliki, Ambroziak K, Dziembowska Teresa, Mavridis Irene M, Photochromism and thermochromism of solid trans-N,N′-bis-(salicylidene)-1,2-cyclohexanediamines and trans-N,N′-bis-(2-hydroxy-naphylidene)-1,2-cyclohexanediamine, 10.1016/s1010-6030(03)00395-2
  52. Xue Pengchong, Lu Ran, Chen Guojun, Zhang Yuan, Nomoto Hiroyuki, Takafuji Makoto, Ihara Hirotaka, Functional Organogel Based on a Salicylideneaniline Derivative with Enhanced Fluorescence Emission and Photochromism, 10.1002/chem.200700321
  53. Chen Peng, Lu Ran, Xue Pengchong, Xu Tinghua, Chen Guojun, Zhao Yingying, Emission Enhancement and Chromism in a Salen-Based Gel System†, 10.1021/la8035727
  54. Rawat, Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem., 26, 232 (1987)
  55. Taneda Masatsugu, Amimoto Kiichi, Koyama Hiroyuki, Kawato Toshio, Photochromism of polymorphic 4,4′-methylenebis(N-salicylidene-2,6-diisopropylaniline) crystals, 10.1039/b311669g
  56. Taneda Masatsugu, Koyama Hiroyuki, Kawato Toshio, Vapor Switching of Photochromism of Methylenebis{N-(3,5-di-tert-butylsalicylidene)aniline} Crystals, 10.1246/cl.2007.354
  57. Taneda Masatsugu, Koyama Hiroyuki, Kawato Toshio, Solvent effects on the crystal photochromism of 4,4′-methylenebis{(N-3,5-di-tert-butylsalicylidene)-2,6-dimethylaniline}, 10.1007/s11164-009-0058-0
  58. Tanaka Koichi, Shimoura Ryota, Caira Mino R., Synthesis, crystal structures and photochromic properties of novel chiral Schiff base macrocycles, 10.1016/j.tetlet.2009.11.062
  59. Pahor Nevenka Bresciani, Calligaris M., Delise P., Dodic G., Nardin G., Randaccio L., Structural effects of the co-ordination of quadridentate Schiff bases to transition-metal atoms. Structure of NN′-(o-phenylene)bis(salicylideneamine) and of its cobalt(II) complex, 10.1039/dt9760002478
  60. Subrahmanyam, Cryst. Struct. Commun., 11, 1719 (1982)
  61. Zhang, Chem. : Res. Chin. Univ., 20, 562 (2004)
  62. Arcovito G., Bonamico M., Domenicano A., Vaciago A., Crystal and molecular structure of salicylaldehyde azine, 10.1039/j29690000733
  63. Xu X. X., You X. Z., Sun Z. F., Wang X., Liu H. X., 2,2'-Azinodimethyldiphenol, C14H12N2O2, 10.1107/s010827019301368x
  64. Mijanuddin Md., Sheldrick W.S., Mayer-Figge H., Ali Mahammad, Chattopadhyay Nitin, Crystal structure and feasibility of intramolecular proton transfer reaction of salicylaldazine, 10.1016/j.molstruc.2004.02.030
  65. Parsons, Private Communication (2004)
  66. El‐Medani S. M., Aboaly M. M., Abdalla H. H., Ramadan R. M., Reactions of Group 6 Metal Carbonyls with Salicylaldehyde Hydrazone, 10.1081/sl-200037610
  67. Liu, Hecheng Huaxue, 12, 219 (2004)
  68. Tang Weixin, Xiang Yu, Tong Aijun, Salicylaldehyde Azines as Fluorophores of Aggregation-Induced Emission Enhancement Characteristics, 10.1021/jo802631m
  69. Birkedal Henrik, Pattison Philip, Bis[4-(salicylideneamino)phenyl]methane, 10.1107/s0108270106003283
  70. Kabak M, Elmali A, Elerman Y, Durlu T.N, Conformational study and structure of bis- N , N ′- p -bromo-salicylideneamine-1,2-diaminobenzene, 10.1016/s0022-2860(00)00573-1
  71. Ha, Acta Cryst., 67, o2234 (2011)
  72. Shahverdizadeh Gholam Hossein, Tiekink Edward R. T., 2-[N-(4-{4-[(E)-(2-Hydroxybenzylidene)amino]phenoxy}phenyl)carboximidoyl]phenol, 10.1107/s1600536811007847
  73. Hadjoudis E., Verganelakis V., Trapalis C., Kordas G., 10.1023/a:1008310718276
  74. Zhang Lei Z., Xiong Ying, Cheng Peng, Tang Guo-Qing, Liao Dai-Zheng, Molecular orbital confinement of a Schiff base molecule in the nanoporous channels of MCM-41 host, 10.1016/s0009-2614(02)00606-1
  75. Sakagami S., Koga T., Takase A., Liquid Crystalline Properties and Photochromism of 4-Halogeno-N-(4-alkoxysalicylidene) anilines, 10.1080/10587250210540
  76. Ziółek Marcin, Sobczak Izabela, Photochromism and hydrolysis of aromatic Schiff base N,N′-bis(salicylidene)-p-phenylenediamine (BSP) studied in heterogeneous environments, 10.1007/s10847-008-9509-2
  77. Kawato Toshio, Kanatomi Hajime, Koyama Hiroyuki, Igarashi Takashi, Photoisomerization and thermoisomerization II: steric requirements for photochromism and thermochromism of N,N'-bis (salicylidene)diamines, 10.1016/0047-2670(86)87034-4
  78. Sliwa Michel, Létard Sylvie, Malfant Isabelle, Nierlich Martine, Lacroix Pascal G., Asahi Tsuyoshi, Masuhara Hiroshi, Yu Pei, Nakatani Keitaro, Design, Synthesis, Structural and Nonlinear Optical Properties of Photochromic Crystals:  Toward Reversible Molecular Switches, 10.1021/cm050929o
  79. Kawato Toshio, Koyama Hiroyuki, Kanatomi Hajime, Isshiki Makiko, Photoisomerization and thermoisomerization I: Unusual photochromism of N-(3,5-di-tert-butyl-salicylidene) amines, 10.1016/0047-2670(85)87020-9
  80. Casades Isabel, Álvaro Mercedes, García Hermenegildo, Pillai Manoj Narayana, Photochemistry of Anils in NaY Zeolite, 10.1002/1099-0690(200207)2002:13<2074::aid-ejoc2074>3.0.co;2-i
  81. Turbeville Wayne., Dutta Prabir K., Spectroscopic studies of the photochromic molecule N-(2-hydroxybenzylidene)aniline and its photoproduct, 10.1021/j100373a033
  82. Sheldrick George M., A short history ofSHELX, 10.1107/s0108767307043930
  83. Bruno Ian J., Cole Jason C., Edgington Paul R., Kessler Magnus, Macrae Clare F., McCabe Patrick, Pearson Jonathan, Taylor Robin, New software for searching the Cambridge Structural Database and visualizing crystal structures, 10.1107/s0108768102003324