Solid state photochromism and thermochromism of two related N-salicylidene anilines

作者: Mihaela Avadanei , Vasile Cozan , Sergiu Shova , José António Paixão

DOI: 10.1016/J.CHEMPHYS.2014.10.007

关键词:

摘要: Abstract The crystalline structure and optical properties of N-salicylidene-p-cyanoaniline N-salicylidene-p-carboxyaniline were investigated in solid state (microcrystalline powder), with the purpose to connect effects substitution crystal packing their properties. Diffuse reflectance fluorescence spectroscopy used study absorption emission upon photoirradiation cooling down liquid nitrogen temperature. Stokes-shifted fluorescence, a quantum yield about 10−2–10−1, is given by tautomeric cis-keto species formed as result excited intramolecular proton transfer from initial enol structure. Despite similar geometrical parameters, only SA-COOH photochromic, which contradiction literature. On other side, thermochromism especially strong at SA-CN. shows behavior SA-CN that classical anil, while presents interesting features contradict presumed based on its supramolecular

参考文章(43)
E. Hadjoudis, A.B. Bourlinos, D. Petridis, The Environmental Effect of MCM-41 Mesoporous Silica on Solid Thermochromic N-(5-Chlorosalicylidene)aniline Journal of Inclusion Phenomena and Macrocyclic Chemistry. ,vol. 42, pp. 275- 279 ,(2002) , 10.1023/A:1016031607524
Marcin Ziółek, Izabela Sobczak, Photochromism and hydrolysis of aromatic Schiff base N,N′-bis(salicylidene)- p -phenylenediamine (BSP) studied in heterogeneous environments Journal of Inclusion Phenomena and Macrocyclic Chemistry. ,vol. 63, pp. 211- 218 ,(2009) , 10.1007/S10847-008-9509-2
Satoshi Kawata, Yoshimasa Kawata, Three-Dimensional Optical Data Storage Using Photochromic Materials. Chemical Reviews. ,vol. 100, pp. 1777- 1788 ,(2000) , 10.1021/CR980073P
Jun Harada, Hidehiro Uekusa, Yuji Ohashi, X-ray Analysis of Structural Changes in Photochromic Salicylideneaniline Crystals. Solid-State Reaction Induced by Two-Photon Excitation Journal of the American Chemical Society. ,vol. 121, pp. 5809- 5810 ,(1999) , 10.1021/JA9842969
Anna Makal, Wojciech Schilf, Bohdan Kamieński, Anna Szady-Chelmieniecka, Eugeniusz Grech, Krzysztof Woźniak, Hydrogen bonding in Schiff bases – NMR, structural and experimental charge density studies Dalton Transactions. ,vol. 40, pp. 421- 430 ,(2011) , 10.1039/C0DT00298D
Keiichiro Ogawa, Yoshiro Kasahara, Yohko Ohtani, Jun Harada, Crystal Structure Change for the Thermochromy of N-Salicylideneanilines. The First Observation by X-ray Diffraction Journal of the American Chemical Society. ,vol. 120, pp. 7107- 7108 ,(1998) , 10.1021/JA980972V
Victor Vargas, Luis Amigo, A study of the tautomers of N-salicylidene-p-X-aniline compounds in methanol Journal of The Chemical Society-perkin Transactions 1. pp. 1124- 1129 ,(2001) , 10.1039/B101041G
Kiichi Amimoto, Toshio Kawato, Photochromism of organic compounds in the crystal state Journal of Photochemistry and Photobiology C-photochemistry Reviews. ,vol. 6, pp. 207- 226 ,(2005) , 10.1016/J.JPHOTOCHEMREV.2005.12.002
Aurélie Plaquet, Maxime Guillaume, Benoît Champagne, Léa Rougier, Fabien Mançois, Vincent Rodriguez, Jean-Luc Pozzo, Laurent Ducasse, Frédéric Castet, Investigation on the Second-Order Nonlinear Optical Responses in the Keto−Enol Equilibrium of Anil Derivatives Journal of Physical Chemistry C. ,vol. 112, pp. 5638- 5645 ,(2008) , 10.1021/JP711511T
Víctor Vargas, Time-Resolved Fluorescence of Salicylideneaniline Compounds in Solution Journal of Physical Chemistry A. ,vol. 108, pp. 281- 288 ,(2004) , 10.1021/JP035461W