Synthesis and unexpected photochemical behaviour of biphotochromic systems involving spirooxazines and naphthopyrans linked by an ethylenic bridge

Samat, A.; Lokshin, Vladimir; Chamontin, Karine; Levi, D. L.; Pèpe, Gérard; Guglielmetti, R.

doi:10.1016/s0040-4020(01)00693-7

Cited by 66 publications

(39 citation statements)

References 22 publications

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“…5-Bromomethylchromene and 3,9-dioxa-6-monoazaundecane were prepared according to the methods reported in ref. [17] and ref. [18] , respectively.…”

Section: Methodsmentioning

confidence: 86%

“…5-Bromomethylchromene was prepared according to a method similar to that found in the literature. [17] The reaction of 5-bromomethylchromene with monoazacrown ethers was undertaken in the presence of triethylamine in dry THF under reflux for 6 h under nitrogen. For comparison with the crowned chromenes, the noncyclic analogue 4 was prepared in a similar fashion.…”

Section: Resultsmentioning

confidence: 99%

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Synthesis and Photochromism of Novel Chromene Derivatives Bearing a Monoazacrown Ether Moiety

et al. 2003

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Crowned chromenes − four novel naphthopyrans (chromenes) bearing monoaza-12-crown-4, -15-crown-5, -18-crown-6, and a noncyclic analogue at the 5-position − were synthesized, and their photochromism in acetonitrile was examined in the presence of alkali and alkaline-earth metal ions. Incorporation of crown ether units to chromene moieties facilitated to a great extent both the thermal isomerization and photoisomerization of the chromene moiety, reflecting the metal-ion-binding ability of the crown ether moiety. Comparison of the crowned chromenes with the cor-

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“…5-Bromomethylchromene and 3,9-dioxa-6-monoazaundecane were prepared according to the methods reported in ref. [17] and ref. [18] , respectively.…”

Section: Methodsmentioning

confidence: 86%

Section: Resultsmentioning

confidence: 99%

Synthesis and Photochromism of Novel Chromene Derivatives Bearing a Monoazacrown Ether Moiety

et al. 2003

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“…After detosylation effected by Na/Hg, deprotected azacrowns 6a,b,c were obtained which were condensed with chloromethyl-spirobenzopyran 7 [11,13], 3-bromomethyl-1-nitroso-2-naphthol 8 [29] and bromomethylchromene 9 [29], respectively, according to literature analogy to give photochromic molecules 2 -4 (Scheme 2).…”

Section: Synthesis Of Photochromic Binaphtho(azacrowns) 2-4mentioning

confidence: 99%

1,1'-Binaphtho(aza)crowns Carrying Photochromic Signalling Unit, I: Synthesis, Characterization and Cation Recognition Properties

Kőszegi

Grűn

Bitter

2006

Supramolecular Chemistry

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S)-1,1'-Binaphtho(monoaza)crown-5,-6 and-7 ionophores carrying photochromic indolospirobenzopyran (SP), naphthoxazine (NO) and naphthopyran (NP) signalling groups were synthesized and their cationinduced isomerisation to the colored merocyanine or quinone forms was studied by UV/Vis spectroscopy in the presence of alkali and alkaline earth metal ions. Under dark conditions the equilibrium of SP and NO dyes were remarkably shifted to the colored form by cations of high positive charge density (Li 1 and alkaline earth metal ions). The same effects were observed with crowned NPs after UV irradiation. The stability of some merocyanine-cation complexes were evaluated by calculating the kinetic parameters of the coloration process.

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“…[5] The influence of the matrix, [6] metal-ion concentration, [7] solvent polarity [8] and pH [9] on the photochromism of variously substituted naphthopyrans has also been reported. Additionally, linking of two photochromic naphthopyrans together [10] or linking a naphthopyran with a spiro[indoline- naphthoxazine] [11] has been investigated. However, the union of a naphthopyran to a traditional dye chromophore has, to the best of our knowledge, not been studied.…”

Section: Introductionmentioning

confidence: 99%

Two Stage Colour Modulation of Triarylmethine Dyes Derived from a Photochromic Naphthopyran

et al. 2008

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The synthesis of the unsymmetrical triarylmethine dyes 4derived from a lithiated naphthopyran and diaryl ketones is reported. In toluene solution 4 display a typical reversible photochromic response becoming coloured upon irradiation with UV light and fading upon cessation of irradiation. At low pH an intensely coloured dye cation is generated and UV irradiation of this solution results in a further colour change as a consequence of photochromic cycling of the naphthopyran unit.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

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Synthesis and unexpected photochemical behaviour of biphotochromic systems involving spirooxazines and naphthopyrans linked by an ethylenic bridge

Cited by 66 publications

References 22 publications

Synthesis and Photochromism of Novel Chromene Derivatives Bearing a Monoazacrown Ether Moiety

Synthesis and Photochromism of Novel Chromene Derivatives Bearing a Monoazacrown Ether Moiety

1,1'-Binaphtho(aza)crowns Carrying Photochromic Signalling Unit, I: Synthesis, Characterization and Cation Recognition Properties

Two Stage Colour Modulation of Triarylmethine Dyes Derived from a Photochromic Naphthopyran

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