Organic Photochromes for Solar Energy Storage

Минкин, В. И.; Breń, V. A.; Lyubarskaya, A. E.

doi:10.1007/978-1-4615-8585-5_5

Cited by 3 publications

(6 citation statements)

References 31 publications

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“…Compounds (2), (3a), (3b), (4a), (4b), (5), and (6) were synthesized according to the previously described procedure [9] (Scheme 1). Compound (4c) was synthesized according to procedure [7].…”

Section: Resultsmentioning

confidence: 99%

“…According to the performed IR and NMR spectral study compounds (2)-(4), (7), and (8) and exocyclic carbonyl groups (1660-1680 cm −1 ). 1 H NMR spectra consist of characteristic signals of methine protons at 8.70-9.00 ppm which correspond to the initial Zconfiguration [3].…”

Section: Photochromic Propertiesmentioning

confidence: 99%

“…1 H NMR spectra consist of characteristic signals of methine protons at 8.70-9.00 ppm which correspond to the initial Zconfiguration [3]. N-Acylated ketoenamines (2)-(4), (7), and (8) absorb in 420-430 nm spectral region (Table 1). On the contrary, compounds (5), (6) correspond to Oacyl derivatives.…”

Section: Photochromic Propertiesmentioning

confidence: 99%

“…They possess typical absorption in the UV spectral region (338-342 nm) [9] and their IR spectra contain ester carbonyl group signals (1720-1750 cm −1 ). For the majority of N-acylated forms A of compounds (3), (4), (7), (8) irradiation (λ irr = 436 nm) of toluene solutions results in Z→E-photoisomerization around the C=C bond followed by a fast thermal N→O acyl migration and S-cis→S-trans isomerization of O-acyl compounds B (Scheme 3, Figure 1). Quantum yields (ϕ) of the A→B photorearrangement include all stages shown on Scheme 3 from Z-A to S-trans-B though we consider all thermal rearrangements to be very rapid [7].…”

Section: Photochromic Propertiesmentioning

confidence: 99%

“…2-(N-Acyl-N-arylaminomethylene)benzo[b]thiophene-3(2H)-ones represent a new family of photochromic molecular switches with fluorescent signalling [1], chiroptical [2], and chemosensor activity [3][4][5]. They may also serve as pH-sensors [6] and solar energy storage systems [7]. However the influence of the size and electronic properties of migrants and substituents in these compounds on their spectral, luminescent, and photochromic properties were insufficiently studied.…”

Section: Introductionmentioning

confidence: 99%

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Acylated 2‐(N‐arylaminomethylene)benzo[b]thiophene‐3(2H)‐Ones: Molecular Switches with Varying Migrants and Substituents

Дубоносов

Rybalkin

Попова

et al. 2009

International Journal of Photoenergy

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Section: Resultsmentioning

confidence: 99%

Section: Photochromic Propertiesmentioning

confidence: 99%

Section: Photochromic Propertiesmentioning

confidence: 99%

Section: Photochromic Propertiesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Acylated 2‐(N‐arylaminomethylene)benzo[b]thiophene‐3(2H)‐Ones: Molecular Switches with Varying Migrants and Substituents

Дубоносов

Rybalkin

Попова

et al. 2009

International Journal of Photoenergy

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Structure and photochromism of 2-(N-acyl-N-arylaminomethylene)benzo[b]thiophen-3(2H)-ones

et al. 2004

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It was shown by electron absorption spectroscopy and X ray diffraction analysis that steric strains in photochromic 2 (N acyl N arylaminomethylene)benzo [b]thiophen 3(2Н ) one mol ecules ortho substituted in the N phenyl ring increase the quantum yield of the N→O photo induced rearrangement in accord with an increase in the steric constant of the ortho sub stituent.✾ Photochromism of 2 (N acyl N arylaminomethyl ene)benzo[b]thiophen 3(2Н ) ones (1) is based on photo initiated Z/E isomerization relatively to the С=С bond followed by the thermal N→O migration of the acyl group (Scheme 1). 1,2Compounds of this type (λ max (1) > λ max (2)) are of interest as systems with negative photochromism, 3,4 whose molecules can accumulate the light energy released dur ing the catalytically controlled process 2 → 1. A wide vari ability of their structures also predetermined a possibility of using ketoenamines 1 as chemosensors for metal cat ions 5,6 (1e), molecular switches of an optical signal 7 (1f), and fluorescent sensors for a change of the pH of a me dium 8 (1g) acting according to principle of the РЕТ ef fect. 9 Reasons for the appearance of chiral properties of ketoenamines 1 ortho substituted in the N phenyl ring were studied. 10 The examples presented show that the structure of a molecule of the type 1, in particular, spatial interactions between the N aryl and N acyl substituents and the heterocyclic moiety, can exert a determining ef fect on the spectral luminescence properties and photo chromism of these compounds. Nevertheless, a relation ship between steric interactions in the ground state in molecules of this type and their spectral and photochemi cal properties (λ max , ε max , λ b ,* ϕ 1→2 ) has not been studied up to date. It can be useful to establish such a relationship for design of chiral chemosensors or switches of an optical signal. According to this, the following tasks of the present Scheme 1 * Long wave absorption boundary λ b with ε ≈ 1.0 L mol -1 cm -1 .

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