User menu

Accès à distance ? S'identifier sur le proxy UCLouvain

First evidence of thermo- and two-step photochromism of tris-anils

Primary tabs

Safin, Damir A. [UCL] Garcia, Yann [UCL]

Seven N,N9,N99-tris(salicylidene)triamines of common formula N(CH2CH2NLCH–aryl) [aryl = 2-OH-C6H4 (1), 2-OH-(5-Cl)C6H3 (2), 2-OH-(5-Br)C6H3 (3), 2,5-(OH)2C6H3 (4), 2,4-(OH)2C6H3 (5), 2,3,4-(OH)3C6H2 (6) and 2-OH-C10H6 (7)] have been synthesized and characterized by elemental analysis, X-ray powder diffraction, NMR, diffuse reflectance, Raman and fluorescence spectroscopy. All the tris-anils are thermochromic. 4 exclusively displays photochromism upon irradiation at 365 nm with a unique two-step back thermal relaxation, with kinetic constants kI = 1.061025 s21 and kII = 4.061025 s21 for the first and second steps, respectively. The origin of the observed photochromism is due to a cis/trans-keto isomerization.

Document type Article de périodique (Journal article) – Article de recherche
Access type Accès restreint
Publication date 2013
Language Anglais
Journal information "RSC Advances" - Vol. 3, no.18, p. 6466 (2013)
Peer reviewed yes
Publisher RSC Publishing
issn 2046-2069
e-issn 2046-2069
Publication status Publié
Affiliation UCL - SST/IMCN/MOST - Molecules, Solids and Reactivity
Links
  1. Senier Alfred, Shepheard Frederick George, LIV.—Salicylidene-m-toluidine, a new phototropic compound; salicylideneamines: salicylamides, 10.1039/ct9099500441
  2. Senier Alfred, Shepheard Frederick George, CCXIV.—Studies in phototropy and thermotropy. Part I. Arylidene- and naphthylidene-amines, 10.1039/ct9099501943
  3. Senier Alfred, Shepheard Frederick George, Clarke Rosalind, CCVII.—Studies in phototropy and thermotropy. Part III. Arylideneamines, 10.1039/ct9120101950
  4. Senier Alfred, Clarke Rosalind, CLXXIX.—Studies in phototropy and thermotropy. Part IV. o-Nitrobenzylidenearylamines and their photoisomeric change, 10.1039/ct9140501917
  5. 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
  6. 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
  7. 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
  8. 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
  9. 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
  10. Cohen M. D., Flavian S., Topochemistry. Part XXIV. The luminescence properties of N-salicylideneaniline and related anils in solution, 10.1039/j29670000317
  11. Cohen M. D., Flavian S., Topochemistry. Part XXV. The absorption spectra of some N-salicylideneanilines and related anils in solution, 10.1039/j29670000321
  12. 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
  13. Cohen M. D., Flavian S., Topochemistry. Part XXVII. The luminescence of crystalline N-salicylideneanilines and related anils, 10.1039/j29670000334
  14. Cohen M. D., Topochemistry. Part XXVIII. The system: 4-chloro-N-salicylideneaniline—4-bromo-N-salicylideneaniline, 10.1039/j29680000373
  15. Hadjoudis, Chem. Soc. Rev., 33, 579 (2004)
  16. Amimoto Kiichi, Kawato Toshio, Photochromism of organic compounds in the crystal state, 10.1016/j.jphotochemrev.2005.12.002
  17. 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
  18. Inokuma Yasuhide, Kawano Masaki, Fujita Makoto, Crystalline molecular flasks, 10.1038/nchem.1031
  19. 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
  20. 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
  21. 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
  22. Robert François, Jacquemin Pierre-Loïc, Tinant Bernard, Garcia Yann, Trans-keto* form detection in non photochromic N-salicylidene aminomethylpyridines, 10.1039/c2ce00006g
  23. Safin Damir A., Robeyns Koen, Garcia Yann, Crown ether-containing N-salicylidene aniline derivatives: synthesis, characterization and optical properties, 10.1039/c2ce25600b
  24. Safin Damir A., Robeyns Koen, Garcia Yann, Solid-state thermo- and photochromism in N,N′-bis(5-X-salicylidene)diamines (X = H, Br), 10.1039/c2ra21631k
  25. Rawat, Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem., 26, 232 (1987)
  26. 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
  27. 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
  28. 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
  29. 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
  30. Sekikawa Taro, Kobayashi Takayoshi, Inabe Tamotsu, Femtosecond Fluorescence Study of Proton-Transfer Process in Thermochromic Crystalline Salicylideneanilines, 10.1021/jp9715888
  31. 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
  32. 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
  33. Taneda Masatsugu, Amimoto Kiichi, Koyama Hiroyuki, Kawato Toshio, Photochromism of polymorphic 4,4′-methylenebis(N-salicylidene-2,6-diisopropylaniline) crystals, 10.1039/b311669g
  34. 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
  35. 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
  36. 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
  37. Hadjoudis Eugene, Chatziefthimiou Spyros, Mavridis Irene, Anils: Photochromism by H-transfer, 10.2174/138527209787314797
  38. 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
  39. 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
  40. 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
  41. 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
  42. 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
  43. Gündüz Necla, Gündüz Turgut, Hursthouse Michael., Parkes Harold G., Shaw (née Gözen) Leylâ S., Shaw Robert A., Tüzün Mürside, X-Ray crystallographic,1H, and13C nuclear magnetic resonance investigation of the potentially heptadentate ligand trensal, 2,2′,2″-tris(salicylideneimino)triethylamine, 10.1039/p29850000899
  44. Zhao, Chem. Res. Chin. Univ., 26, 687 (2010)
  45. KANESATO Masatoshi, NGASSAPA Faustin Nazareno, YOKOYAMA Toshiro, Crystal Structure of Tris(((5-chlorosalicylidene)amino)ethyl)amine., 10.2116/analsci.16.781
  46. Figuet Mélanie, Averbuch-Pouchot Marie Thérèse, d’Hardemare Amaury du Moulinet, Jarjayes Olivier, Tripodal Iminophenolate Ligand Complexes of Gallium(III), Indium(III), and Thallium(III), 10.1002/1099-0682(200108)2001:8<2089::aid-ejic2089>3.0.co;2-b
  47. Zhang, Jiegou Huaxue, 24, 371 (2005)
  48. Hadjoudis E., Verganelakis V., Trapalis C., Kordas G., 10.1023/a:1008310718276
  49. 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
  50. Sakagami S., Koga T., Takase A., Liquid Crystalline Properties and Photochromism of 4-Halogeno-N-(4-alkoxysalicylidene) anilines, 10.1080/10587250210540
  51. 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
  52. 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
  53. 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
  54. 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
  55. 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
  56. Turbeville Wayne., Dutta Prabir K., Spectroscopic studies of the photochromic molecule N-(2-hydroxybenzylidene)aniline and its photoproduct, 10.1021/j100373a033
  57. Chong C., Varret F., Boukheddaden K., Evolution of self-organized spin domains under light in single-crystalline[Fe(ptz)6](BF4)2, 10.1103/physrevb.81.014104
  58. Broomhead JA, Robinson DJ, A potential septadentate ligand, 10.1071/ch9681365
  59. Mustapha Abdullahi, Busch Krystoff, Patykiewicz Marta, Apedaile Alistair, Reglinski John, Kennedy Alan R., Prior Timothy J., Multidentate ligands for the synthesis of multi-metallic complexes, 10.1016/j.poly.2007.11.016
  60. Mustapha Abdullahi, Reglinski John, Kennedy Alan R., Armstrong David R., Sassmannshausen Jörg, Murrie Mark, Multidentate Ligands for the Synthesis of Multimetallic Complexes. 2. Formation of a Planar Cu4OH Motif, 10.1021/ic100594n
Bibliographic reference Safin, Damir A. ; Garcia, Yann. First evidence of thermo- and two-step photochromism of tris-anils. In: RSC Advances, Vol. 3, no.18, p. 6466 (2013)
Permanent URL http://hdl.handle.net/2078.1/127461