User menu

1,2,4-triazole based molecular switches: crystal structures, Hirshfeld surface analysis and optical properties

Bibliographic reference Safin, Damir ; Robeyns, Koen ; Garcia, Yann. 1,2,4-triazole based molecular switches: crystal structures, Hirshfeld surface analysis and optical properties. In: CrystEngComm, (2016)
Permanent URL http://hdl.handle.net/2078.1/175577
  1. Bertarelli C., Bianco A., Castagna R., Pariani G., Photochromism into optics: Opportunities to develop light-triggered optical elements, 10.1016/j.jphotochemrev.2011.05.003
  2. P. Bamfield and M. G.Hutchings, Technological Applications of Colour Chemistry, Chromic Phenomena, Royal Society of Chemistry, Cambridge, 2010
  3. Irie M., Photochromism:  Memories and SwitchesIntroduction, 10.1021/cr980068l
  4. Kobatake Seiya, Irie Masahiro, 8  Photochromism, 10.1039/b208508a
  5. 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
  6. Hadjoudis, Chem. Soc. Rev., 33, 579 (2004)
  7. Amimoto Kiichi, Kawato Toshio, Photochromism of organic compounds in the crystal state, 10.1016/j.jphotochemrev.2005.12.002
  8. 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
  9. Hadjoudis Eugene, Chatziefthimiou Spyros, Mavridis Irene, Anils: Photochromism by H-transfer, 10.2174/138527209787314797
  10. Inokuma Yasuhide, Kawano Masaki, Fujita Makoto, Crystalline molecular flasks, 10.1038/nchem.1031
  11. Hadjoudis E., Verganelakis V., Trapalis C., Kordas G., 10.1023/a:1008310718276
  12. 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
  13. Robert, J. Phys.: Conf. Ser., 217, 012031 (2010)
  14. Garcia Yann, Robert François, Naik Anil D., Zhou Guangyuan, Tinant Bernard, Robeyns Koen, Michotte Sébastien, Piraux Luc, Spin Transition Charted in a Fluorophore-Tagged Thermochromic Dinuclear Iron(II) Complex, 10.1021/ja205974q
  15. Robert François, Naik Anil D., Tinant Bernard, Garcia Yann, N-Salicylidene anil anions as thermo-sensitive components of organic–inorganic hybrid materials, 10.1016/j.ica.2011.08.040
  16. Jacquemin Pierre-Loïc, Garcia Yann, Devillers Michel, Blends made from N-salicylidene aniline sulfonate derivatives and a polyampholyte matrix: in situ synthesis vs. solution mixing, 10.1039/c3tc31979b
  17. 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
  18. Robert François, Jacquemin Pierre-Loïc, Tinant Bernard, Garcia Yann, Trans-keto* form detection in non photochromic N-salicylidene aminomethylpyridines, 10.1039/c2ce00006g
  19. Safin Damir A., Robeyns Koen, Garcia Yann, Crown ether-containing N-salicylidene aniline derivatives: synthesis, characterization and optical properties, 10.1039/c2ce25600b
  20. 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
  21. Jacquemin Pierre-Loïc, Robeyns Koen, Devillers Michel, Garcia Yann, Reversible photochromism of an N-salicylidene aniline anion, 10.1039/c3cc45080e
  22. Jacquemin Pierre-Loïc, Robeyns Koen, Devillers Michel, Garcia Yann, Photochromism Emergence inN-Salicylidenep-Aminobenzenesulfonate Diallylammonium Salts, 10.1002/chem.201406573
  23. Custelcean Radu, Jackson James E., Dihydrogen Bonding:  Structures, Energetics, and Dynamics, 10.1021/cr000021b
  24. C. Schalley , Introduction in Analytical Methods in Supramolecular Chemistry, ed. C. Schalley, WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim, 2007, pp. 1–16
  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. 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
  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, 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
  41. 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
  42. Ceyhan Gökhan, Köse Muhammet, McKee Vickie, Uruş Serhan, Gölcü Ayşegül, Tümer Mehmet, Tetradentate Schiff base ligands and their complexes: Synthesis, structural characterization, thermal, electrochemical and alkane oxidation, 10.1016/j.saa.2012.04.001
  43. Safin Damir A., Garcia Yann, First evidence of thermo- and two-step photochromism of tris-anils, 10.1039/c3ra40705e
  44. Safin Damir A., Robeyns Koen, Babashkina Maria G., Filinchuk Yaroslav, Rotaru Aurelian, Jureschi Catalin, Mitoraj Mariusz P., Hooper James, Brela Mateusz, Garcia Yann, Polymorphism driven optical properties of an anil dye, 10.1039/c6ce00266h
  45. Rotaru Aurelian, Dugay Julien, Tan Reasmey P., Guralskiy Ilya A., Salmon Lionel, Demont Philippe, Carrey Julian, Molnár Gábor, Respaud Marc, Bousseksou Azzedine, Nano-electromanipulation of Spin Crossover Nanorods: Towards Switchable Nanoelectronic Devices, 10.1002/adma.201203020
  46. Lefter Constantin, Tan Reasmey, Dugay Julien, Tricard Simon, Molnár Gábor, Salmon Lionel, Carrey Julian, Rotaru Aurelian, Bousseksou Azzedine, Light induced modulation of charge transport phenomena across the bistability region in [Fe(Htrz)2(trz)](BF4) spin crossover micro-rods, 10.1039/c4cp05250a
  47. Garcia Yann, van Koningsbruggen Petra J., Codjovi Epiphane, Lapouyade René, Kahn Olivier, Rabardel Louis, Non-classical FeII spin-crossover behaviour leading to an unprecedented extremely large apparent thermal hysteresis of 270 K: application for displays, 10.1039/a701242j
  48. Kahn O., Spin-Transition Polymers: From Molecular Materials Toward Memory Devices, 10.1126/science.279.5347.44
  49. Linares Jorge, Codjovi Epiphane, Garcia Yann, Pressure and Temperature Spin Crossover Sensors with Optical Detection, 10.3390/s120404479
  50. Jureschi Cătălin, Linares Jorge, Rotaru Aurelian, Ritti Marie, Parlier Michel, Dîrtu Marinela, Wolff Mariusz, Garcia Yann, Pressure Sensor via Optical Detection Based on a 1D Spin Transition Coordination Polymer, 10.3390/s150202388
  51. Cuéllar Manuel Pegalajar, Lapresta-Fernández Alejandro, Herrera Juan Manuel, Salinas-Castillo Alfonso, Pegalajar María del Carmen, Titos-Padilla Silvia, Colacio Enrique, Capitán-Vallvey Luis Fermín, Thermochromic sensor design based on Fe(II) spin crossover/polymers hybrid materials and artificial neural networks as a tool in modelling, 10.1016/j.snb.2014.11.025
  52. Jureschi Catalin-Maricel, Linares Jorge, Boulmaali Ayoub, Dahoo Pierre, Rotaru Aurelian, Garcia Yann, Pressure and Temperature Sensors Using Two Spin Crossover Materials, 10.3390/s16020187
  53. Gütlich P, Photoswitchable coordination compounds, 10.1016/s0010-8545(01)00381-2
  54. Herchel Radovan, Pavelek Lubomír, Trávníček Zdeněk, Dinuclear and 1D iron(iii) Schiff base complexes bridged by 4-salicylideneamino-1,2,4-triazolate: X-ray structures and magnetic properties, 10.1039/c1dt11127b
  55. Scott Hayley S., Ross Tamsyn M., Moubaraki Boujemaa, Murray Keith S., Neville Suzanne M., Spin Crossover in Polymeric Materials Using Schiff Base Functionalized Triazole Ligands, 10.1002/ejic.201201071
  56. Wu Tao, Zhang Xiao-Peng, You Xiao-Zeng, Li Yi-Zhi, Bouř Petr, Chirality Transfer in Magnetic Coordination Complexes Monitored by Vibrational and Electronic Circular Dichroism, 10.1002/cplu.201300429
  57. Spackman Mark A., Jayatilaka Dylan, Hirshfeld surface analysis, 10.1039/b818330a
  58. Spackman Mark A., McKinnon Joshua J., Fingerprinting intermolecular interactions in molecular crystals, 10.1039/b203191b
  59. Jelsch Christian, Ejsmont Krzysztof, Huder Loïc, The enrichment ratio of atomic contacts in crystals, an indicator derived from the Hirshfeld surface analysis, 10.1107/s2052252514003327
  60. Blatov Vladislav A., Shevchenko Alexander P., Proserpio Davide M., Applied Topological Analysis of Crystal Structures with the Program Package ToposPro, 10.1021/cg500498k
  61. McKinnon Joshua J., Mitchell Anthony S., Spackman Mark A., Hirshfeld Surfaces: A New Tool for Visualising and Exploring Molecular Crystals, 10.1002/(sici)1521-3765(19981102)4:11<2136::aid-chem2136>3.0.co;2-g
  62. A. I. Kitaigorodsky , Molecular Crystals and Molecules, Academic Press, New York, 1973
  63. Safin Damir A., Mitoraj Mariusz P., Robeyns Koen, Filinchuk Yaroslav, Vande Velde Christophe M. L., Luminescent mononuclear mixed ligand complexes of copper(i) with 5-phenyl-2,2′-bipyridine and triphenylphosphine, 10.1039/c5dt02755a
  64. Babashkina Maria G., Robeyns Koen, Filinchuk Yaroslav, Safin Damir A., Detailed studies of the interaction of 3-chloroaniline with O,O′-diphenylphosphorylisothiocyanate, 10.1039/c5nj02588e
  65. Sheldrick George M., A short history ofSHELX, 10.1107/s0108767307043930
  66. Sheldrick George M., Crystal structure refinement withSHELXL, 10.1107/s2053229614024218
  67. Spek Anthony L., Structure validation in chemical crystallography, 10.1107/s090744490804362x
  68. 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