16111-07-2

Usage

Chemical Properties

Dark red solid

Upstream product

• 36508-00-6 (R/S)-9,9,9a-trimethyl-2,3,9,9a-tetrahydrooxazolo[3,2-a]indole 
• 97-51-8 5-Nitrosalicylaldehyde 
• 27344-29-2 2-(3,3-dimethyl-2-methylene-2,3-dihydro-1H-indol-1-yl)-1-ethanol 
• 93633-69-3 C₆H₄C(CH₃)2NCH₂CH₂OHCOCHCHC₆H₃NO₂ 
• 549507-77-9 protonated merocyanine 
• 93633-69-3 6-[2-[1-(2-Hydroxy-ethyl)-3,3-dimethyl-1,3-dihydro-indol-(2Z)-ylidene]-eth-(Z)-ylidene]-4-nitro-cyclohexa-2,4-dienone 
• 1640-39-7 2,3,3-trimethylindoleniune 
• 540-51-2 2-bromoethanol 
• 29636-94-0 1-(2-hydroxyethyl)-2,3,3-trimethyl-3H-indol-1-ium bromide 

Downstream Products

• 25952-50-5 1-(β-methacryloxyethyl)-3,3-dimethyl-6'-nitrospiro(indoline-2,2'-<2H>benzopyran) 
• 126078-42-0 1'-<2-(2-Benzoylbenzoyloxy)ethyl>-3,3'-dimethyl-6-nitrospiro<2H-1-benzopyran-2,2'-indoline> 
• 93633-69-3 C₆H₄C(CH₃)2NCH₂CH₂OHCOCHCHC₆H₃NO₂ 
• 863646-23-5 p-nitrophenyl 2-(3',3'-dimethyl-6-nitro-3'H-spiro[chromene-2,2'-indole]-1'-yl)ethyl carbonate 
• 1239910-85-0 C₃₅H₃₈N₂O₆ 
• 93633-69-3 6-[2-[1-(2-Hydroxy-ethyl)-3,3-dimethyl-1,3-dihydro-indol-(2Z)-ylidene]-eth-(Z)-ylidene]-4-nitro-cyclohexa-2,4-dienone 
• 1380212-14-5 1'-{2-[(S)-methacryloyloxypropanoyloxy]ethyl}-3',3'-dimethyl-6-nitrospiro(2H-1-benzopyran-2,2'-indoline) 
• 1380212-17-8 1'-(2-{(S)-2-[(S)-methacryloyloxypropanoyloxy]propanoyloxy}ethyl)-3',3'-dimethyl-6-nitrospiro(2H-1-benzopyran-2,2'-indoline) 

Relevant academic research and scientific papers

All-optical integrated logic operations based on chemical communication between molecular switches

Molecular logic gates process physical or chemical "inputs" to generate "outputs" based on a set of logical operators. We report the design and operation of a chemical ensemble in solution that behaves as integrated AND, OR, and XNOR gates with optical in

Photochemical switching of luminescence and singlet oxygen generation by chemical signal communication

Photoluminescence in the far red spectral region and photosensitised generation of singlet oxygen, with associated near-IR emission, are reversibly controlled by near-UV or violet light in a communicating ensemble of molecular switches.

Optical switching of the Dirac point in graphene multilayer field-effect transistors functionalized with spiropyran

A facile method for achieving optical switching of the Dirac point and conductance in reduced graphene oxide multilayer FETs that are non-covalently functionalized with a photo-responsive spiropyran derivative is presented. The photoresponsive transition from spiropyran to merocyanine induces the reversible optical switching in graphene based FETs.

Controlling contact electrification with photochromic polymers

Charge switching: Control of contact electrification was achieved using a combination of photoreactive polymers and light. Upon UV irradiation, polymers substituted with photochromic spiropyrans reversibly switch their rate, and depending on chemical structure, their sign of charging by contact electrification (see picture). Consistent with empirical predictions, these photochromic polymers tended to charge positively upon irradiation with UV light.

Light-responsive micelles of spiropyran initiated hyperbranched polyglycerol for smart drug delivery

Light-responsive polymeric micelles have emerged as site-specific and time-controlled systems for advanced drug delivery. Spiropyran (SP), a wellknown photochromic molecule, was used to initiate the ring-opening multibranching polymerization of glycidol to afford a series of hyperbranched polyglycerols (SP-hb-PG). The micelle assembly and disassembly were induced by an external light source owing to the reversible photoisomerization of hydrophobic SP to hydrophilic merocyanine (MC). Transmission electron microscopy, atomic force microscopy, UV/vis spectroscopy, and dynamic light scattering demonstrated the successful assembly and disassembly of SP-hb-PG micelles. In addition, the critical micelle concentration (CMC) was determined through the fluorescence analysis of pyrene to confirm the amphiphilicity of respective SP-hb-PG n(n = 15, 29, and 36) micelles, with CMC values ranging from 13 to 20 mg/L, which is correlated to the length of the polar polyglycerol backbone. Moreover, the superior biocompatibility of the prepared SP-hb-PG was evaluated using WI-38 cells and HeLa cells, suggesting the prospective applicability of the micelles in smart drug delivery systems.

Negative Photochromism of Solutions of Functionalized Spiropyrans in a Water—Acetonitrile Mixture

A spectral-kinetic study of photochromic functionalized nitro-substituted indoline spiropyrans in water-acetonitrile mixtures has allowed to observe for the first time the effect of negative photochromism due to the self-assembly of photochromic molecules in a mixed solvent with the formation of hydrogen bonds and proton complexes.

Microwave-assisted crystallization inclusion of spiropyran molecules in indium trimesate films with antidromic reversible photochromism

An indium trimesate metal-organic framework (JUC-120) which possesses a cubic zeolitic MTN topology, as a new analogue to MIL-100(Al, Fe or Cr) compounds, has been successfully synthesized. Its structure exhibits a mesoporous cage (26 A) and high thermal stability. The assembly of nitrobenzospiropyran derivatives (BSP) into JUC-120 nanocrystals (BSP/JUC-120) is achieved by a microwave-assisted crystallization inclusion approach. The BSP/JUC-120 films have been prepared on quartz wafers by a spin-coating method. The successful encapsulation of BSP molecules into the mesopores of the JUC-120 structure has been verified by N2 adsorption and TGA measurements. The photochromic properties of BSP/JUC-120 films are studied by the UV-Vis and fluorescence spectroscopies. More interestingly, metastable open merocyanine (OMC) species are directly generated from the closed spiropyran form (CSP) without photoirradiation and stabilized for a long period in the BSP/JUC-120 film. The open merocyanine isomer bleaches to the closed spiropyran form by ultraviolet or visible light, and the coloration is regained upon standing in the dark, exhibiting antidromic photochromism. Moreover, the BSP/JUC-120 film shows high reversibility and thermal stability of photochromism. This highly efficient MOF film is expected to be promising in the applications of optical devices.

Reversible fluorescence switching of spiropyran-conjugated biodegradable nanoparticles for super-resolution fluorescence imaging

We report on the reversible fluorescence switching of biodegradable nanoparticles of spiropyran-terminated poly(ε-caprolactone) (SP-PCL) for super-resolution fluorescence imaging. SP-PCL was synthesized via ring-opening polymerization using hydroxyl-conta

Novel syntheses of bis-spiropyran photochromic compounds using ultrasound II

bis-Spiropyran photochromic compounds derivatives (3', 3'- trimethylindoline-2-spiro-2'-benzopyran), were synthesized using ultrasonic energy (25 kHz, 55 Watts). The reaction times were between 10 to 20 min. and higher yields comparing with the conventional reported methods, were obtained.

Photochromism in cucurbit[8]uril cavity: Inhibition of hydrolysis and modification of the rate of merocyanine-spiropyran transformations

The effect of inclusion complex formation on the photochromic behavior of a spirobenzopyran dye and its merocyanine isomer was studied in aqueous solution using cucurbit[8]uril (CB8) as a host. The merocyanine (MC) and protonated merocyanine (MCH+) were the most stable forms both in water and inside the cavity of CB8. The equilibrium constant of 1:1 complexation with CB8 was found to be 1.7 × 105 and 2.0 × 106 M -1 for the former and latter species, respectively. The encapsulation led to significant change in the rate of the photoinduced and thermal photochromic transformations and hindered the hydrolysis of MC. The effect of CB8 on the reaction kinetics strongly altered with pH. The transition from the spiropyran form to trans-MC in a thermal reaction had 33 kJ mol-1 lower activation energy and more than 5 orders of magnitude smaller Arrhenius pre-exponential factor in CB8 than in water.