Photochromism of several synthesised 1,3-diazabicyclo[3,1,0]hex-3-ene derivatives

Mahmoodi, Nosrat O.; Zanjanchi, Mohammad Ali; Kiyani, Hamzeh

doi:10.3184/0308234041423772

Cited by 35 publications

(21 citation statements)

References 11 publications

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“…The melting points were a In the solid state. [17], 2,3-dibromo-3-(4-nitrophenyl)-1-phenylpropan-1-one (XIV) [11,13], and [3-(4-nitrophenyl)aziridin-2-yl](phenyl)methanone (XV) [10] were prepared according to known methods.…”

Section: Methodsmentioning

confidence: 99%

“…In the present article we report on several new photochromic compounds that are derivatives of well known photochromic 1,3-diazabicyclo[3.1.0]hex-3-ene system. Compounds I-XII with different substituents in the 2-position were synthesized following a slightly modified known procedure [10][11][12][13][14] (Scheme 1). Benzoylaziridines XV were prepared starting from chalcones XIII which were subjected to bromination at the double bond with bromine in chloroform solution to obtain dibromo derivatives XIV, followed by aziridination with a solution of ammonia in anhydrous ethanol at room temperature [10].…”

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NMR structural elucidation and photochromic behavior of new 1,3-diazabicyclo[3.1.0]hex-3-ene derivatives

et al. 2010

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Several 6-(4-nitrophenyl)-4-phenyl-1,3-diazabicyclo[3.1.0]hex-3-ene derivatives having various substituents on C 2 were synthesized, and their 1 H NMR spectra and photochromic behavior were examined.* The text was submitted by the authors in English.Study on photochromic materials has drawn great attention due to their applications in optical data storage devices, holographic storage, solar cells, and sensitizers [1,2]. Photochromism is a vast field encompassing well-known phenomena associated with reversible transformations upon irradiation with UV and visible light. In this chemical process, a compound absorbs electromagnetic radiation and undergoes a reversible change between two states that display different absorption spectra, i.e. different colors. In the recent time, various photochromic dyes have been developed to improve major photochromic properties such as reversibility and stability [3,4].We have recently become interested in photochromism and photoreproduction of 3,5-diazabicyclo-[3.1.0]hex-3-ene derivatives with various substituents [5]. In addition, synthesis of several fluorescence emission producers based on symmetrical and unsymmetrical trisannelated benzene constructions was attempted [6,7]. Applications of photochromic compounds directly depend upon color change produced by variation of the molecular and electronic structures in going from the initial to photoinduced form and their corresponding absorption or emission spectra. They can be used as variable-transmission optical materials for photochromic ophthalmic lenses or camera filters, fluid flow visualization, optical information storage, novelty items (e.g., toys, T-shirts, etc.), authentication systems (security printing inks), and cosmetics. Requirements for photonics devices are as follows: (1) thermal stability of both isomers, (2) low fatigue, i.e., the possibility for recycling without loss of performance, (3) repeatable cycle number > 10 4 , (4) high sensitivity (quantum yield > 0.5), (5) rapid response, (6) non-destructive readout capability, and (7) reactivity in the solid state. Among these, thermal stability and fatigue resistance are the most important.We recently used novel potentiometric membrane sensors based on 6-(4-nitrophenyl)-2,4-diphenyl-3,5-diazabicyclo[3.1.0]hex-2-ene and 6-(4-nitrophenyl)-2-phenyl-4,4-dipropyl-3,5-diazabicyclo[3.1.0]hex-2-ene for detection of tin(II) [8] and strontium(II) ions [9], respectively, at trace levels in real samples. In the present article we report on several new photochromic compounds that are derivatives of well known photochromic 1,3-diazabicyclo[3.1.0]hex-3-ene system. Compounds I-XII with different substituents in the 2-position were synthesized following a slightly modified known procedure [10-14] (Scheme 1). Benzoylaziridines XV were prepared starting from chalcones XIII which were subjected to bromination at the double bond with bromine in chloroform solution to obtain dibromo derivatives XIV, followed by aziridination with a solution of ammonia in anhydrous ethanol at room tempe...

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Section: Methodsmentioning

confidence: 99%

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confidence: 99%

NMR structural elucidation and photochromic behavior of new 1,3-diazabicyclo[3.1.0]hex-3-ene derivatives

et al. 2010

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“…

It was also reported that oximes could be converted into N-unsubstituted aziridines by treatment with Grignard reagents or by reduction with lithium aluminum hydride in certain cases [17].

3,3-Pentamethyleneoxaziridine can transfer its NH group to electron-deficient olefins to give N-unsubstituted aziridines in low yields [17,18].

…”

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confidence: 99%

“…by bromination of the related α,β-unsaturated carbonyl compounds, followed with the reaction of ammonia solution [5][6][7][8][9][10].…”

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Aminopyridinium iodide as a NH transferring agent for the synthesis of 2-aroyl-3-aryl aziridines

Samimi

Momeni

2015

J IRAN CHEM SOC

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by bromination of the related α,β-unsaturated carbonyl compounds, followed with the reaction of ammonia solution [5][6][7][8][9][10].Another synthetic pathway for the synthesis of aziridinyl ketones involves formation of β-hydroxyamino derivatives followed by treatment with either metal alcoholates, or hydroxylamine hydrochloride and then potassium hydroxide [11][12][13][14]. It has been reported the interaction of unsaturated ketones with N-tosyliminoaryliodinanes in the presence of mono-valent copper complexes produces the related aziridinyl ketone [15,16].It was also reported that oximes could be converted into N-unsubstituted aziridines by treatment with Grignard reagents or by reduction with lithium aluminum hydride in certain cases [17].3,3-Pentamethyleneoxaziridine can transfer its NH group to electron-deficient olefins to give N-unsubstituted aziridines in low yields [17,18]. 2-ketoaziridine starting materials were also prepared using 1,4-addition of methoxyamine to α,β-unsaturated ketones followed by basepromoted ring closure [19]. Ylides are another kind of potential NH transfer agent. Free sulfimides HN = SR 2 , sulfur-nitrogen ylide [20][21][22][23][24], are used for the direct synthesis of N-unsubstituted aziridines. An one step synthesis of aziridine by the type addition off free sulfimide has been reported but yields are unsatisfactory and enaminoketones are obtained as major byproducts in moderate yields.On the other hand, an amineimide, as a type of nitrogennitrogen ylide, is an effective NH source for direct N-unsubstituted aziridination of electron-deficient olefins. Recently, a few method has been reported that tertiary amines such as N-methylmorpholin [25], 1,4-diazabicyclo[2.2.2]octane (DABCO) [26,27]. Quinine chiral tertiary amine [28] and Troger s base [29] can prepare amine imide which reacts with chalcone to give desire aziridinyl ketones (Scheme 1).Abstract A new approach for the synthesis of N-H ketoaziridines is described. 1-aminopyridinium iodide as a NH transferring agent provides a straightforward access to the 2-aroyl-3-arylaziridines from the corresponding 1,3-diarylprop-2-en-1-one. A possible general mechanism involving the N-N ylide is proposed.

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“…A digital pH meter (Corning Model 125) was used for measuring pH. The ionophore, 6-(4-nitrophenyl)-2-phenyl-4,4-dipropyl-3,5-diaza-bicyclo[3,1,0]hex-2-ene, was synthesized according to procedure described previously [16]. All reagents used were of analytical reagent grade.…”

Section: Apparatus and Reagentsmentioning

confidence: 99%

A Fast Response Strontium Ion‐Selective Electrode Prepared by Sol‐Gel Membrane Technique

et al. 2009

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A sol-gel electrode, based on 6-(4-nitrophenyl)-2-phenyl-4,4-dipropyl-3,5-diaza-bicyclo [3,1,0] hex-2-ene (NPDBH) as a neutral ionophore, was successfully developed for the detection of Sr 2þ in aqueous solutions. Theoretical calculations confirmed NPDBH selectivity toward strontium in comparison with some other metal ions. The electrode responds to Sr 2þ ion with a sensitivity of 29.1 AE 0.4 mV/decade over the range 8.0 Â 10 À7 -1.0 Â 10 À1 M. Selectivity coefficients determined by matched potential method (MPM) indicate high selectivity for strontium ions. The electrode has a fast response time of 11 s and a working pH range of 3.0 -10.0. The sol-gel electrode shows detection limit of 7.5 Â 10 À8 M.

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Photochromism of several synthesised 1,3-diazabicyclo[3,1,0]hex-3-ene derivatives

Abstract: Several 1,3-diazabicyclo[3,1,0]hex-3-ene derivatives with varying substitutions such as 9H-fluorenyl, 4-(cyclohexyl-phenyl)-2-methyl, 4-cyclohexyl phenyl, 2-phenyl-2-methyl, and 2-cyclohexyl-2-phenyl that behave as ‘intelligent material’ are reported.

Cited by 35 publications

References 11 publications

NMR structural elucidation and photochromic behavior of new 1,3-diazabicyclo[3.1.0]hex-3-ene derivatives

NMR structural elucidation and photochromic behavior of new 1,3-diazabicyclo[3.1.0]hex-3-ene derivatives

Aminopyridinium iodide as a NH transferring agent for the synthesis of 2-aroyl-3-aryl aziridines

A Fast Response Strontium Ion‐Selective Electrode Prepared by Sol‐Gel Membrane Technique

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