2005
DOI: 10.1021/cm050929o
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Design, Synthesis, Structural and Nonlinear Optical Properties of Photochromic Crystals:  Toward Reversible Molecular Switches

Abstract: Two new anil molecules exhibiting photochromism in the crystalline state, N-(4-hydroxy)-salicylideneamino-4-(methylbenzoate) (2) and N-(3,5-di-tert-butylsalicylidene)-4-aminopyridine (3), are obtained. Upon irradiation in the UV, the yellow crystals change color to red, owing to enol-keto intramolecular tautomerism. The red color disappears, when crystals are left in the dark or irradiated with visible light. 3 has the most stable keto form among all anil-type photochromic compounds (τ ) 460 days at room tempe… Show more

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Cited by 236 publications
(199 citation statements)
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“…Molecular crystals have increasingly attracted great attention due to their peculiar chemical and physical properties, which make them suitable as high energy-density materials, [1][2][3] active pharmaceutical ingredients (APIs), [4][5][6] constituents of opto-electronic devices for their linear and non-linear optical properties, [7][8][9] etc.…”
mentioning
confidence: 99%
“…Molecular crystals have increasingly attracted great attention due to their peculiar chemical and physical properties, which make them suitable as high energy-density materials, [1][2][3] active pharmaceutical ingredients (APIs), [4][5][6] constituents of opto-electronic devices for their linear and non-linear optical properties, [7][8][9] etc.…”
mentioning
confidence: 99%
“…4P was obtained by the condensation of equimolar amounts of 3,5-di-tert-butylsalicylaldehyde and 4-aminopyridine respectively as mentioned elsewhere [32]. Purity of the product was checked by their melting point, FTIR spectra, NMR spectrum and Elemental analysis.…”
Section: Synthesismentioning
confidence: 99%
“…This study also confirmed the cold cis-keto* as the main precursor of the trans-keto photoproduct. More recently, our interest focused on the study of N-(3,5-di-tert-butylsalicylidene)-4-aminopyridine (4P, see Figure 1), the salicylidene aminopyridine with the longest lifetime for the trans-keto form in solid state (more than one year) [32]. Furthermore, its second-order non linear optical properties are particularly interesting [33].…”
Section: Introductionmentioning
confidence: 99%
“…Over the past several decades, crystal engineering has attracted much attention not only because of the versatile structures but also due to the far ranging applications such as those in nonlinear optical, magnetic, and catalytic fields [4][5][6][7].…”
Section: Introductionmentioning
confidence: 99%