1592-43-4Relevant articles and documents
Molecular structure, spectroscopic and quantum chemical studies of 1′,3′,3′-trimethylspiro[benzo[f]chromene-3,2′-indoline
Asiri, Abdullah M.,Ersanli, Cem Cüneyt,?ahin, Onur,Arshad, Muhammad Nadeem,Hameed, Salem A.
, p. 108 - 117 (2016)
In this work, synthesis, X-ray single crystal determination, nuclear magnetic resonance (1H NMR and 13C NMR), Ultraviolet-Visible (UV-vis), Fourier transform infrared spectroscopy (FT-IR) and quantum mechanical studies of the 1′,3′,3′-trimethylspiro[benzo[f]chromene-3,2′-indoline [(C23H21NO), TMSBCI] have been both experimentally and theoretically reported. The molecular structure obtained from X-ray single-crystal analysis of the investigated compound in the ground state has been compared using Hartree-Fock (HF) and density functional theory (DFT) with the functional B3LYP using the 6-31G(d,p) as basis set. In addition to the optimized geometrical structures, atomic charges, molecular electrostatic potential (MEP) and natural bond orbital (NBO) have been investigated by using B3LYP/6-31G(d,p) level of the theoretical approximation for the title compound. The energetic behavior of TMSBCI has been examined in solvent media using polarizable continuum model (PCM). The total dipole moment (μ), the average linear polarizability (α), and the first-order hyperpolarisability (β) values of the investigated molecule have been computed using the same method. The experimental measurements (1H NMR, 13C NMR and UV-vis) have been compared with its corresponding the calculated values (using DFT). Besides, frontier molecular orbitals (FMOs) and thermodynamic properties have also been studied.
Spiropyrans and spirooxazines and preparation method thereof
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Paragraph 0074; 0077; 0078; 0079; 0106; 0107, (2019/01/22)
The invention provides spiropyrans, naphthospiropyrans and spirooxazines. The invention also relates to a method for preparing the spiropyrans, the naphthospiropyrans and the spiroxazines by reactionof indole compounds, especially indole iodide, with alde
Greener route for the synthesis of photo- and thermochromic spiropyrans using a highly efficient, reusable, and biocompatible choline hydroxide in an aqueous medium
Pargaonkar, Jyotsna G.,Patil, Sanjay K.,Vajekar, Shailesh N.
supporting information, p. 208 - 215 (2017/12/26)
Here, we report the synthesis of photo- and thermochromic spiropyrans promoted by a highly efficient, biocompatible, and reusable choline hydroxide (ChOH) in greener solvent water. This procedure provides several advantages such as simple workup, mild reaction conditions, short reaction time, and high yields of the products. Furthermore, the ChOH could be reused at least five times without significantly losing its catalytic activity. The structures of the synthesized spiropyran derivatives were confirmed by several characterization methods such as 1H NMR, 13C NMR, and mass spectra.
Comparative Evaluation of Substituent Effect on the Photochromic Properties of Spiropyrans and Spirooxazines
Balmond, Edward I.,Tautges, Brandon K.,Faulkner, Andrea L.,Or, Victor W.,Hodur, Blanka M.,Shaw, Jared T.,Louie, Angelique Y.
, p. 8744 - 8758 (2016/10/14)
Spiropyrans and spirooxazines represent an important class of photochromic compounds with a wide variety of applications. In order to effectively utilize and design these photoswitches it is desirable to understand how the substituents affect photochromic properties, and how the different structural motifs compare under identical conditions. In this work a small library of photoswitches was synthesized in order to comparatively evaluate the effect of substituent modifications and structure on photochromism. The library was designed to modify positions that were believed to have the greatest effect on C-O bond lability and therefore the photochromic properties. Herein we report a comparative analysis of the UV and visible light responses of 30 spiropyrans, spiroindolinonaphthopyrans, and spirooxazines. The influence of gadolinium(III) binding was also investigated on the library of compounds to determine its effect on photoswitching. Both assays demonstrated different trends in substituent and structural requirements for optimal photochromism.
Spiropyrans and spirooxazines 6. the spectral and kinetic properties of 5-(4,5-diphenyl-1,3-oxazol-2-yl)-substituted spironaphthopyrans: An experimental and theoretical study
Chernyshev,Dorogan,Voloshin,Metelitsa,Minkin
scheme or table, p. 456 - 464 (2011/11/04)
The spectral and kinetic properties of 5-(4,5-diphenyl-1,3-oxazol-2-yl) spiro[indoline-naphthopyran] derivatives were studied by experimental and theoretical methods. The additional long-wavelength maximum in the absorption spectra of compounds studied is due to the introduction of a diphenyloxazole fragment and corresponds to a π-π*electronic transition with a partial charge transfer character. Substituents have little effect on the kinetic parameters of the spironaphthopyrans studied.
Photochromism of spirobenzopyranindolines and spironaphthopyranindolines
Chibisov,Goerner
, p. 424 - 431 (2007/10/03)
The photocolouration of five spiro[2H-1-benzopyran-2,2′-indoline] compounds (1-5) and two spironaphthopyranindolines (6, 7) to give the ring-opened merocyanine(s) and the subsequent thermal relaxation back to the closed form was studied. A trans-merocyanine but no cis-photoisomer were detected for 1-7 using λexc = 308 nm and a singlet pathway accounts for photocolouration. In contrast to nitrospiropyrans the yield of colouration of spiropyrans is essentially independent of solvent polarity. The relaxation times at 25°C range from 0.01 s for 6 in methylcyclohexane to 17 s for 5 in ethanol, which is due to differences in both activation energies (65-80 kJ mol-1) and the pre-exponential factor (1012-1014 s-1). The photomerocyanine yield is substantially increased upon naphthalene- or acetone-sensitized excitation, where otherwise the same spectral changes, relaxation time and activation parameters were found. Upon excitation of the trans-merocyanine (λexc = 530 nm), a cis-merocyanine with lifetime in the sub ms range could be detected at lower temperatures. Deactivation of the excited trans-merocyanine occurs mainly in the excited singlet state. For 4 and 5, due to an internal heavy-atom effect of bromine substituents, and for 1, a triplet state as a precursor of the cis- and trans-merocyanines could be observed. The effects of structure and medium properties on the photoprocesses are described and the mechanisms of photochromism and thermal decolouration are discussed.
