38660-35-4

Basic information

• Product Name: 3',6'-bis(diethylamino)-2-phenylspiro[1H-isoindole-1,9'-[9H]xanthene]-3(2H)-one
• Synonyms: 3',6'-bis(diethylamino)-2-phenylspiro[1H-isoindole-1,9'-[9H]xanthene]-3(2H)-one;3,6-Bis(diethylamino)-2'-phenylspiro[9H-xanthene-9,1'-[1H]isoindol]-3'(2'H)-one;Aids125535;Aids-125535;Nsc75508;Spiro[1H-isoindole-1,9'-[9H]xanthen]-3(2H)-one, 3',6'-bis(diethylamino)-2-phenyl-;3',6'-Bis(DiethylaMino)-2-Phenylspiro[Isoindole-3,9'-Xanthene]-1-One;3',6'-Bis(diethylaMino)-2-phenylspiro[isoindoline-1,9'-xanthen]-3-one
• CAS NO: 38660-35-4
• Molecular Formula: C₃₄H₃₅N₃O₂
• Molecular Weight: 517.6606
• EINECS: 254-066-2
• Mol File: 38660-35-4.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 691.5°Cat760mmHg
• Flash Point: 372°C
• Appearance: /
• Density: 1.25g/cm³
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 3',6'-bis(diethylamino)-2-phenylspiro[1H-isoindole-1,9'-[9H]xanthene]-3(2H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3',6'-bis(diethylamino)-2-phenylspiro[1H-isoindole-1,9'-[9H]xanthene]-3(2H)-one(38660-35-4)
• EPA Substance Registry System: 3',6'-bis(diethylamino)-2-phenylspiro[1H-isoindole-1,9'-[9H]xanthene]-3(2H)-one(38660-35-4)

Safety Data

• Hazardous Substances Data: 38660-35-4(Hazardous Substances Data)

Usage

General Description

The chemical compound "3',6'-bis(diethylamino)-2-phenylspiro[1H-isoindole-1,9'-[9H]xanthene]-3(2H)-one" is a spiropyran derivative that is commonly used as a pH indicator in analytical chemistry. It is a solid, pink-colored compound that undergoes a reversible color change from pink to colorless in response to changes in pH. This characteristic makes it useful for monitoring acidity and alkalinity in a variety of chemical and biological systems. The compound has also been studied for its potential applications in photochromic materials and sensors due to its reversible photoisomerization behavior. Overall, "3',6'-bis(diethylamino)-2-phenylspiro[1H-isoindole-1,9'-[9H]xanthene]-3(2H)-one" is a versatile compound with potential uses in various fields, including chemistry, materials science, and sensor technology.

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Relevant articles and documents

A new rhodamine-based fluorescent chemosensor for transition metal cations synthesized by one-step facile condensation

A new rhodamine-based fluorescent chemosensor (1) for transition metal cations was synthesized by one-step facile condensation of rhodamine B and 2-aminopyridine. Without metal cations, 1 is colorless and nonfluorescent, whereas addition of metal cations (Fe3+, Hg2+, Pb2+, and Fe2+) leads to an obvious color change to pink and an appearance of orange fluorescence.

KINETIC STUDIES OF SOLVENT AND PRESSURE EFFECTS ON THERMAL ISOMERIZATIONS OF N-PHENYL- AND N-METHYLRHODAMINELACTAMS

Solvent and pressure effects were examined for the isomerization rates of N-phenyl- and N-methylrhodaminelactams (RL-Ph and RL-CH3) from their zwitterionic to the spiro forms.From the pressure dependence of the reaction rate, the activation volumes were estimated to be about 5 cm3mol-1 for RL-Ph and 3-10 cm3mol-1 for RL-CH3.It is proposed that there are two rotameric isomers for the coloured zwitterionic forms, and the role of these rotamers in the kinetic effects of solvent and pressure is discussed.The results are consistent with a reaction mechanism involving heterolytic ring closure on activation.

Long-Lived Charge-Transfer State Induced by Spin-Orbit Charge Transfer Intersystem Crossing (SOCT-ISC) in a Compact Spiro Electron Donor/Acceptor Dyad

We prepared conceptually novel, fully rigid, spiro compact electron donor (Rhodamine B, lactam form, RB)/acceptor (naphthalimide; NI) orthogonal dyad to attain the long-lived triplet charge-transfer (3CT) state, based on the electron spin control using spin-orbit charge transfer intersystem crossing (SOCT-ISC). Transient absorption (TA) spectra indicate the first charge separation (CS) takes place within 2.5 ps, subsequent SOCT-ISC takes 8 ns to produce the 3NI* state. Then the slow secondary CS (125 ns) gives the long-lived 3CT state (0.94 μs in deaerated n-hexane) with high energy level (ca. 2.12 eV). The cascade photophysical processes of the dyad upon photoexcitation are summarized as 1NI*→1CT→3NI*→3CT. With time-resolved electron paramagnetic resonance (TREPR) spectra, an EEEAAA electron-spin polarization pattern was observed for the naphthalimide-localized triplet state. Our spiro compact dyad structure and the electron spin-control approach is different to previous methods for which invoking transition-metal coordination or chromophores with intrinsic ISC ability is mandatory.

Study of Rhodamine-Based Fluorescent Probes for Organic Radical Intermediates

Rhodamine-based amide derivatives for the detection of radical intermediates in organic reactions were synthesized and used as fluorescent probes over a wide range of solvents. The mechanistic studies confirm a reversible opening and closing of the spirolactam ring. Compound 21 can be used to support the radical mechanism or in the real-time monitoring of radical intermediates.

A Multisite-Binding Switchable Fluorescent Probe for Monitoring Mitochondrial ATP Level Fluctuation in Live Cells

Adenosine triphosphate (ATP), commonly produced in mitochondria, is required by almost all the living organisms; thus fluorescent probes for monitoring mitochondrial ATP levels fluctuation are essential and highly desired. Herein, we report a multisite-binding switchable fluorescent probe, ATP-Red 1, which selectively and rapidly responds to intracellular concentrations of ATP. Live-cell imaging indicated that ATP-Red 1 mainly localized to mitochondria with good biocompatibility and membrane penetration. In particular, with the help of ATP-Red 1, we successfully observed not only the decreased mitochondrial ATP levels in the presence of KCN and starvation state, but also the increased mitochondrial ATP levels in the early stage of cell apoptosis. These results indicate that ATP-Red 1 is a useful tool for investigating ATP-relevant biological processes. Illuminating the ATP: A multisite-binding, switchable fluorescent probe can selectively and rapidly respond to ATP at intracellular concentrations. In live-cell imaging, the probe was successfully applied to monitor fluctuations in mitochondrial ATP levels.