13433-31-3

Usage

Uses

Used in Smart Materials:
1,3,3-Trimethylindolino-8'-methoxybenzopyrylospiran is used as a photochromic material for its ability to change color upon UV light exposure, making it suitable for applications in smart materials that require dynamic color changes.
Used in Data Storage:
1,3,3-TRIMETHYLINDOLINO-8'-METHOXYBENZOPYRYLOSPIRAN is used as a component in data storage systems, where its photochromic properties can be exploited to encode and decode information through color changes upon exposure to light.
Used in Optics:
1,3,3-Trimethylindolino-8'-methoxybenzopyrylospiran is used in the optics industry as a photochromic material for applications that require light-sensitive elements, such as lenses and optical filters that adjust their properties based on light exposure.
Used in Safety Equipment:
1,3,3-TRIMETHYLINDOLINO-8'-METHOXYBENZOPYRYLOSPIRAN is used in the development of safety equipment, such as protective eyewear and clothing, that can change color in response to UV light, providing an additional layer of protection and visibility for users in certain environments.

InChI:InChI=1/C20H21NO2/c1-19(2)15-9-5-6-10-16(15)21(3)20(19)13-12-14-8-7-11-17(22-4)18(14)23-20/h5-13H,1-4H3

Upstream product

• 118-12-7 1,3,3-Trimethyl-2-methyleneindoline 
• 148-53-8 3-methoxy-2-hydroxybenzaldehyde 
• 5418-63-3 1,2,3,3-tetramethyl-3H-indolium iodide 
• 64-17-5 ethanol 

Relevant academic research and scientific papers

Synthesis, optical properties and in vitro cell viability of novel spiropyrans and their photostationary states

A novel class of spiropyran (SP) was synthesized using a multistep process that involves three key intermediates: (a) diazonium-tetrafluoroborate, (b) hydrazine and (c) indolium iodide. Single crystal X-ray spectroscopy was used to confirm the structure of one of the analogues. The SP analogues were confirmed as being able to isomerize and attain a photostationary state (PSS) upon irradiation with ultraviolet light (UV, 365 nm) in an aqueous environment. UV–visible absorption spectra were recorded to confirm the isomerization properties. The ability of the synthesized compounds to induce growth inhibition of HeLa cervical cancer cells was assessed via the MTT assay after incubation with either the SP or their PSS. The IC50 values of two PSS (PSS-2, 4), were observed to be around 14 ± 4 fold lower (26 ± 3 μM) than their corresponding SPs. The most cytotoxic compounds SP-7 and PSS-7 showed the lowest IC50 values (12 μM). An in vitro tubulin polymerization assay showed that SP-7 and PSS-7 exhibited the greatest difference in tubulin inhibition relative to unirradiated SP-1 and SP-4.

Photochromism of spirobenzopyranindolines and spironaphthopyranindolines

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.

Greener route for the synthesis of photo- and thermochromic spiropyrans using a highly efficient, reusable, and biocompatible choline hydroxide in an aqueous medium

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.

To estimation of pKa for spiropyrans of the indoline series

A mathematically substantiated approach to estimating acid-base characteristics of spiropyrans of the indoline series with account for the ring-chain tautomerism of these compounds was proposed. The pKa values of spiropyrans of various basicity were estimated.

Novel syntheses of spiropyran photochromatic compounds using ultrasound

Photochromatic derivatives 1,3,3-trimethylindoline-2-spiro-2'-benzopyran, were synthesized using ultrasound as energy source (55 watt), reaction times are between 10 to 20 min, obtaining higher or slightly lower yield than the conventional reported methods.

Photo-polymerizable composition containing an acid salt of an indolinobenzospiropyran

A photo-polymerizable composition comprising (A) a photopolymerization initiator comprising at least one inorganic or organic acid salt of an indolinobenzospiropyran represented by the following general formula (I): SPC1 wherein R1 represents an alkyl group, substituted alkyl group or a phenyl group; R2 and R3 each represents an alkyl group or a phenyl group or, when taken together, R2 and R3 form a methylene chain CH2 wherein n is an integer of 4 or 5; X represents a hydrogen atom, a nitro group, a halogen atom, a carboxy group; and Y represents one or more substituents selected from the group consisting of a hydrogen atom, a nitro group, a halogen atom, a formyl group and an alkoxy group, and (B) at least one cationically polymerizable substance.