Synthese De Quelques Spiro[Indoline‐Naphtoxazines] Et Spiro[Indoline‐Pyridobenzoxazines] Photochromiques. Application De La Methodologie De La Recherche Experimentale

Pottier, E.; Sergent, Michelle; Luu, R. Phan Tan; Guglielmetti, R.

doi:10.1002/bscb.19921010810

Cited by 42 publications

(19 citation statements)

References 15 publications

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“…17 3H Indolium iodides 7a,c-g were synthesized according to the methods described earlier. [18][19][20][21] Sodium 5 chloro 2 hydroxybenzoate (2). A mixture of 5 chloro 2 hydroxybenzoic acid 1 (8.63 g, 50 mmol) and sodium methoxide (2.70 g, 50 mmol) in methanol (40 mL) was refluxed for 2 h. Methanol was half evaporated in vacuo followed by the addition of ether (30 mL).…”

Section: Methodsmentioning

confidence: 99%

Spiropyrans and spirooxazines 5. Synthesis of photochromic 8-(4,5-diphenyl-1,3-oxazol-2-y1)-substituted spiro[indoline-benzopyrans]

et al. 2009

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Photochromic spiro[indoline benzopyrans] containing 4,5 diphenyloxazolyl group at position 8 of the benzopyran fragment have been obtained. New diphenyloxazolyl substituted spiropyrans manifest considerably higher thermal stability of the merocyanine isomers than their naphthopyran analogs.The synthesis and studies of new efficient photochro mic systems, prospective for development of polyfunc tional materials for molecular electronics on their basis, is an actual problem. 2,3 Among the most well known classes of photochromic compounds, spiropyrans are of particu lar interest since, depending on molecular structures, they manifest spectro kinetic characteristics varying in a wide range, as well as due to the relative easiness of their synthesis. 3-5Mechanism of photochromic transformations of spiro pyrans (SPP) (Scheme 1) includes the thermally and photochemically reversible process of heterolytic cleavage Scheme 1 of the C Sp -O bond of the cyclic isomer A with subse quent cis-trans isomerization to the metastable mero cyanine form B. 3-5On the basis of SPP by introduction of the corre sponding functional fragments, it is possible to obtain polyfunctional molecular systems displaying, along with photochromism, fluorescent, 6 magnetic, 7 and complex forming properties switching by optical irradiation. 8 Earlier, 9 we reported on the synthesis of photochromic 5´ (4,5 diphenyl 1,3 oxazol 2 yl) substituted spiro[indoline naphthopyran], the merocyanine form of which reversibly forms complexes with bivalent cations of heavy metals. In continuation of this research, the present work deals with the synthesis and description of photochromic properties of a number of spirobenzopyrans containing diphenyl oxazolyl group at position 8 of the benzopyran fragment. Results and DiscussionThere are two general methods for the synthesis of SPP. The first of them (method I) includes a condensation of corresponding heterocyclic cations with o hydroxy aromatic aldehydes in acidic medium, isolation of salts of o hydroxystyryl derivatives, and spirocyclization of the latter under the action of a base. Method II, used the most often for the preparation of indoline SPP, consists in condensation of a methylene base (or the correspond ing heterocyclic immonium salt in the presence of a base) with o hydroxyaromatic aldehydes. Both methods have been used for the synthesis of indoline SPP containing diphenyloxazolyl substituent (Scheme 2).

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Section: Methodsmentioning

confidence: 99%

Spiropyrans and spirooxazines 5. Synthesis of photochromic 8-(4,5-diphenyl-1,3-oxazol-2-y1)-substituted spiro[indoline-benzopyrans]

et al. 2009

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“…The sodium salt of the acid 6a, the desyl chloride 7, and the 3H-indolium salts 2a-d were obtained by the previously described methods [16,[21][22][23][24][25].…”

Section: Methodsmentioning

confidence: 99%

Photochromic and thermochromic spiranes. 34.* synthesis of photochromic 5-(4,5-diphenyl-1,3-oxazol-2-yl)-substituted spirobenzochromeneindolines

Voloshin

Chernyshev

Метелица

2011

Chem Heterocycl Comp

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“…Methyleneindoline 5 (obtained from Lancaster) and methyleneindoline 6 (obtained from Aldrich) were used without further purification. Methyleneindoline 7 was prepared according to Pottier [25], while aldehyde 8 was prepared according to our previous procedure [9].…”

Section: Methodsmentioning

confidence: 99%

Photo- and thermochromic spiranes. 31.* Photochromic cationic spiropyrans with a pyridinium fragment in the aliphatic side chain*2

Voloshin

Bezugliy

Соловьева

et al. 2008

Chem Heterocycl Comp

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Syntheses are reported for cationic indoline spiropyrans with a quaternized pyridinium fragment in the aliphatic side chain, which display photochromic properties in solution. The major effect of introducing a quaternized pyridinium fragment into the benzopyran part of the spiropyran entails a significant decrease in the rate of thermal relaxation processes.Keywords: cationic indolinospiropyrans, pyridinium fragment, photochromism, electronic absorption spectroscopy.Photochromic organic molecules, some of which are spiropyrans and spirooxazines, have recently been the subject of intensive research due to the use of these compounds in optical recording and data transformation systems, sensors, optical electronics, optical bioelectronics, and transport systems [2-5].However, the limit to improving the characteristics of monofunctional materials has now been reached and attention is being directed toward the development of hybrid polyfunctional materials holding promise for application in molecular electronics.A possible solution of this problem lies in the creation of hybrid polyfunctional materials, which combine structural units responsible for different physicochemical properties such as photochromism and magnetism [6][7][8][9], photochromism and conductivity [10,11], electrical and magnetic properties [12], and optical dichroism and magnetism [13]. A systematic study of both the structure and properties of such units and the feasibility of their combination into a single crystal lattice is required for the development of such materials from molecular units differing in their chemical nature, the investigation of the interaction of such units on each other, and methods for the modification of the properties of the separate units to impart desired properties to the hybrid materials. _______ * For Communication 30 see [1]. * 2 Dedicated to Academician of the Russian Academy of Sciences B. A. Trofimov on his 70th jubilee. __________________________________________________________________________________________

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Synthese De Quelques Spiro[Indoline‐Naphtoxazines] Et Spiro[Indoline‐Pyridobenzoxazines] Photochromiques. Application De La Methodologie De La Recherche Experimentale

Cited by 42 publications

References 15 publications

Spiropyrans and spirooxazines 5. Synthesis of photochromic 8-(4,5-diphenyl-1,3-oxazol-2-y1)-substituted spiro[indoline-benzopyrans]

Spiropyrans and spirooxazines 5. Synthesis of photochromic 8-(4,5-diphenyl-1,3-oxazol-2-y1)-substituted spiro[indoline-benzopyrans]

Photochromic and thermochromic spiranes. 34.* synthesis of photochromic 5-(4,5-diphenyl-1,3-oxazol-2-yl)-substituted spirobenzochromeneindolines

Photo- and thermochromic spiranes. 31.* Photochromic cationic spiropyrans with a pyridinium fragment in the aliphatic side chain*2

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