27333-47-7

Usage

Uses

Used in Molecular Electronics:
1,3,3-Trimethylindolinonaphthospirooxazine is used as a photochromic dye for its ability to change color upon exposure to UV light. This characteristic is particularly useful in molecular electronics, where it can be employed in the development of optical switches and other light-sensitive devices.
Used in Printing Materials:
In the printing industry, 1,3,3-Trimethylindolinonaphthospirooxazine is used as a smart colorant due to its photochromic properties. This allows for the creation of materials that can change color in response to UV light, offering new possibilities for dynamic and interactive designs.
Used in Ophthalmic Lenses:
1,3,3-Trimethylindolinonaphthospirooxazine is also utilized in the development of ophthalmic lenses, such as smart glasses or sunglasses. The photochromic nature of the dye enables the lenses to automatically adjust their tint in response to changes in sunlight, providing a more comfortable and adaptive visual experience for the wearer.

InChI:InChI=1/C22H20N2O/c1-21(2)17-10-6-7-11-18(17)24(3)22(21)14-23-20-16-9-5-4-8-15(16)12-13-19(20)25-22/h4-14H,1-3H3

Upstream product

• 118-12-7 1,3,3-Trimethyl-2-methyleneindoline 
• 131-91-9 1-Nitroso-2-naphthol 
• 101515-24-6 1-[(E)-1,3,3-Trimethyl-1,3-dihydro-indol-(2Z)-ylidenemethylimino]-1H-naphthalen-2-one 
• 2834-92-6 1-amino-2-naphthol 
• 124729-25-5 1-[(Z)-1,3,3-Trimethyl-1,3-dihydro-indol-(2E)-ylidenemethylimino]-1H-naphthalen-2-one 
• 5418-63-3 1,2,3,3-tetramethyl-3H-indolium iodide 
• 1198-27-2 1-aminonaphthalene-2-ol hydrochloride 
• 33941-15-0 1-aza-18-crown-6 
• 66943-05-3 1,4,7,10-tetraoxa-15-azacyclopentadecane 
• 124729-25-5 merocyanine 
• 101515-24-6 1-[(Z)-1,3,3-Trimethyl-1,3-dihydro-indol-(2Z)-ylidenemethylimino]-1H-naphthalen-2-one 

Downstream Products

• 19155-24-9 3,3-dimethyloxindole 
• 20200-86-6 1,3,3-trimethyl-1,3-dihydro-2H-indol-2-one 
• 233-70-5 naphtho[1,2-d]oxazole 
• 194918-33-7 1,3,3-trimethylindoline carboxylic acid 
• 2834-92-6 1-amino-2-naphthol 

Relevant academic research and scientific papers

Synthesis of photochromic spirooxazines from 1-amino-2-naphthols

A synthetic access to photochromic spirooxazines is developed through the condensation of methylene-substituted azaheterocycles on 1-amino-2- naphthols in presence of an oxidizing agent. Compared to usual preparation of this kind of compounds (via 1-nitroso-2-naphthols), yields are generally good and approaches to further spiroheterocyclic oxazines are possible.

Light-induced change of the molecular charge in a spironaphthoxazine compound

To evaluate the experimental conditions for the light-induced change of the molecular charge, the dependence of the photochromic reaction behaviour of the indolino spiro naphthoxazine compound 1,3,3-trimethyl-spiro[2H-indol 2,3'[3H]naphth[2,1-b]-[1,4]oxazine] on the pH value of the solution is investigated. In the absence of UV light an acid-base equilibrium between the spiro form and a protonated closed form is established. By irradiation under appropriate acidic conditions the spiro form can be transformed into an open cationic form through the merocyanine form. Between the two open forms an acid-base equilibrium is established. Except for the closed protonated form the structures are confirmed by mean of NMR. The kinetics of the thermal ring-closing reaction of both forms are investigated by flash photolysis. It is shown that the ring-closing reaction proceeds exclusively via the merocyanine form. The pK values determined for both equilibria give the pH range, in which the light-induced change of the molecular charge occurs.

Photochromic Processes in Spiro(1,3,3-trimethylindolo-2,2'-naphth-1,4-oxazine) studied using Two-laser Two-colour Techniques

The photochemistry of the photomerocyanine from the title compound shows dramatic differences between polar and non-polar media; in the latter it involves the intermediacy of a ground state species with a lifetime of ca. 4 μs which regenerates the merocyanine almost quantitatively.

Sub-picosecond transient absorption spectroscopy of substituted photochromic spironaphthoxazine compounds

The photochromic reaction dynamics of spiroindolinenaphthoxazine and its 6′CN and 5′CHO substituted compounds is investigated in different solvents by femtosecond transient absorption spectroscopy. In addition to the formation of the merocyanine coloured form (ring-opened trans form, OF), another short-lived intermediate species is produced upon photoexcitation, which is not a precursor to the OF product but which is formed in parallel to it via a competing relaxation process. This species is ascribable to either a relaxed s-cis ring-opened isomer on the ground state potential energy surface or to a metastable minimum of the excited S1 state potential energy surface of the ring-closed form. The observed kinetics suggest that the production of OF (photocoloraton reaction) is controlled by the efficiency of the competing process rather than by an s-cis - trans isomerisation energy barrier.

Structures and photochromic properties of substituted spiroindolinonaphthoxazines

Six indolinospironaphthoxazines were studied by X-ray diffraction analysis. It was demonstrated that the electronic nature of the substituents in the naphthoxazine and indoline fragments has no substantial effect on the Cspiro-O and Cspiro-N bond lengths. Photocolorability of the compounds under study depends only slightly on the above-mentioned bond lengths and correlates mainly with the energy of steric strain of the oxazine ring. The stability of the open forms of spiroindolinonaphthoxazines that formed upon photoirradiation is determined to a large extent by the electronic and steric nature of the substituents. The exception is the compound that contains the NO2 group in the indoline fragment. In the last-mentioned case, the cleavage of the ring occurs through a substantially different pathway.

The pH Control of the Decolouration Rate of Spironaphthoxazine Derivatives

The thermal stablility of the coloured open form of 5-methoxy- (7) and 5'-piperidinomethyl-1,3,3-trimethylspiro(indoline-2,3'-naphthooxazine) (6) is strongly dependent on pH.

A method for synthesizing spiroxime photochromic dyes using a microchannel reactor

The present invention relates to a method of synthesizing a photochromic dye using a microchannel reactor. In the coupling ring process in the late stage of dye synthesis, after the temperature of the mobile phase system containing the reaction raw material is adjusted to the reaction temperature by the pre-reaction system, the above-mentioned mobile phase is pumped into the microchannel reactor by means of a constant current pump for mixed temperature control reaction, and a solution containing photochromic dye is obtained, and the photochromic dye is obtained by concentration, recrystallization, decolorization and drying. This method uses the high mixing and heat exchange efficiency of the microchannel to ensure the full mixing of the reactants and the accuracy of temperature control, the energy saving effect is good, the production cost is reduced, the purity of the product is high, the difficulty of subsequent processing is reduced, the mobile phase can be reused, and it is convenient for large-scale production, which has a broad application prospect.

Highly efficient green synthesis of the photochromic spironaphthoxazines using an eco-friendly choline hydroxide catalyst

A greener route for the synthesis of the photochromic spironaphthoxazines employing a highly efficient, biodegradable and recyclable choline hydroxide catalyst in an aqueous medium has been described. This methodology offers diverse advantages such as mild reaction conditions, short reaction time (1 h), excellent yields (up to 91%), and operational simplicity that make it a useful and attractive option for the synthesis of the spironaphthoxazines. The choline hydroxide showed excellent catalytic performance until five recycles without significant loss of activity. The structures of synthesized spironaphthoxazines were deduced by their 1H NMR spectra and melting points.

Spiropyrans and spirooxazines and preparation method thereof

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

Spirooxazine photochromic compound

The invention relates to a spirooxazine photochromic compound which has the following general formula (1), wherein R is selected from any one of the group consisting of H, NMe2, Cu (OH) 3, Me and oMe,R' is selected from any one selected from the group consisting of NMe2, CF3, H, NO2 and CN. The spirooxazine photochromic compound is prepared by reacting an indole iodide with a nitroso compound.