84100-84-5

Usage

Chemical Properties

Yellow Solid

Flammability and Explosibility

Notclassified

InChI:InChI=1/C12H13NO2/c1-7-12(2,3)9-6-8(11(14)15)4-5-10(9)13-7/h4-6H,1-3H3,(H,14,15)

Upstream product

• 563-80-4 3-methyl-butan-2-one 
• 619-67-0 4-Hydrazinobenzoic acid 
• 150-13-0 4-amino-benzoic acid 
• 24589-77-3 4-hydrazinobenzoic acid hydrochloride 
• 126442-84-0 4-(1,2-dimethyl-propylidenehydrazino)-benzoic acid 

Downstream Products

• 1211408-63-7 5-carboxy-1-(4-carboxybenzyl)-2,3,3-trimethyl-3H-indol-1-ium bromide 
• 1424614-29-8 C₃₁H₂₆N₂O₂ 

Relevant academic research and scientific papers

Substituent effect in direct ring functionalized squaraine dyes on near infra-red sensitization of nanocrystalline TiO2 for molecular photovoltaics

We have synthesized a series of novel blue colored symmetrical squaraine sensitizers with variable alkyl chain length for their application towards the fabrication of dye-sensitized solar cells (DSSCs). It has been found that an increase in the alkyl chain length substituted at N-position of indole ring exhibits enhanced electron diffusion length and electron life-time resulting in better passivation of nanocrystalline TiO2 surface leading to enhancement in the cell performance. Based on HOMO and LUMO energy measurement of squaraine dyes, it has been demonstrated that about 0.16 eV energy barrier is sufficient for electron injection from LUMO of dye to TiO2 conduction band and dye regeneration after photo-excitation. Performances of DSSCs using model squaraine dyes indicate that dodecyl alkyl substituent is optimum giving highest Voc and use of chenodeoxycholic acid along with the dye SQ-4 shows a photoconversion efficiency of 3.5% under AM 1.5 irradiation.

Ratiometric luminescence detection of hydrazine with a carbon dots-hemicyanine nanohybrid system

It is significant to develop probes for rapid, selective, and sensitive detection of highly toxic hydrazine in both environmental and biological science. In this work, under mild conditions, through the electrostatic attraction between negatively charged CDs and positively charged hemicyanine molecules, a novel ratiometric fluorescent probe containing CDs and a hemicyanine derivative was fabricated for reliable, selective, and sensitive sensing of hydrazine. This nanohybrid system possesses dual emission peaks at 550 and 610 nm under a single excitation wavelength of 530 nm. The addition of hydrazine to CDs-hemicyanine nanohybrid solution results in complete fluorescence quenching of the hemicyanine derivative, while the orange fluorescence of CDs remains constant. Furthermore, the CDs-hemicyanine nanohybrid system shows high selectivity toward hydrazine over other various species, including some nucleophilic species, metal ions and anions. The limit of quantification (LOQ) was 0-1 mM and the detection limit was as low as 8.0 μM.

A ratiometric fluorescent sensor for pH fluctuation and its application in living cells with low dark toxicity

It is highly demanded and challenging to develop small-molecular fluorescent sensors for the ratiometric detection of pH fluctuation. A ratiometric fluorescent pH sensor was constructed by integrating a pH-sensitive fluorophore with a pH-insensitive hemicyanine group. Its linear and reversible ratiometric fluorescent response from pH 7.0 to 8.8 and 6.0 to 9.0 respectively makes this sensor suitable for the practical tracking of pH fluctuation in live cells. With this sensor, stimulated pH fluctuation has been successfully tracked in a ratiometric manner via fluorescence imaging with low dark toxicity.

A novel colorimetric and ratiometric pH sensor with a notably large Stokes shift for sensing extremely alkaline solution

In this work, a facile hemicyanine-naphthalene-based fluorescent sensor for colorimetric and ratiometric sensing of pH was constructed via a simple synthesis process. Significantly, sensor 3 showed a high sensitivity to extremely alkaline solution and had a notably large Stokes shift (145 nm). Its absorbance and fluorescence enhanced or quenched obviously in the pH range of 5.0–12.0, accompanying with colour change. In addition, the fluorescence intensity increased 727-fold (F440/F710) when the pH was adjusted to 12, indicating that sensor 3 showed great potential in the detection of extremely alkaline solution.

A novel colorimetric and fluorescent probe based on indolium salt for detection of cyanide in 100% aqueous solution

We reported a novel indolium salt -based colorimetric and fluorescent probe N1 for cyanide. The probe N1 showed a bleaching solution and fluorescence quenching toward CN? in 100% aqueous solution over other anions. In UV-vis and fluorescent spectrometry method, a large blue shift (261 nm), color bleaching and fluorescence quenching was observed. The minimum detection limit on fluorescence response of the probe N1 towards CN? was 3.34 × 10?7 mol/L. This probe N1 operates via intramolecular charge transfer (ICT) mechanism, because the nucleophilic attacking of CN? to the indol C[dbnd]N, the ICT progress was blocked with color changed and fluorescence quenched, which is further confirmed by 1H NMR, MS and DFT studies. Therefore, the synthesized probe would be a promising device for the detection of cyanide.

A Rhodium-Cyanine Fluorescent Probe: Detection and Signaling of Mismatches in DNA

We report a bifunctional fluorescent probe that combines a rhodium metalloinsertor with a cyanine dye as the fluorescent reporter. The conjugate shows weak luminescence when free in solution or with well matched DNA but exhibits a significant luminescence increase in the presence of a 27-mer DNA duplex containing a central CC mismatch. DNA photocleavage experiments demonstrate that, upon photoactivation, the conjugate cleaves the DNA backbone specifically near the mismatch site on a 27-mer fragment, consistent with mismatch targeting. Fluorescence titrations with the 27-mer duplex containing the CC mismatch reveal a DNA binding affinity of 3.1 × 106 M-1, similar to that of other rhodium metalloinsertors. Fluorescence titrations using genomic DNA extracted from various cell lines demonstrate a clear discrimination in fluorescence between those cell lines that are proficient or deficient in mismatch repair. This differential luminescence reflects the sensitive detection of the mismatchrepair-deficient phenotype.

A coumarin-connected carboxylic indolinium sensor for cyanide detection in absolute aqueous medium and its application in biological cell imaging

Fluorescent sensor has been noticed in detecting system due to its sensitive, selective, operational simplicity and low cost. We designed a coumarin-connected carboxylic indolium sensor molecule that is water-soluble and cytomembrane-permeable. This infrared (IR) emitter is selectively sensitive towards cyanide detection in aqueous media according to CN? nucleophilic attack on the indole C=N function. Upon the addition of CN? anion, the color of sensor in water varied from blue to colorless by naked eyes and fluorescence quenching was observed by spectroscopic method. This was because the intramolecular charge transfer (ICT) effect occurred when the fluorescent sensor was added with CN?. The minimum detection limit of the sensor's fluorescence response to CN? is 4.44 × 10?7 mol/L. Furthermore, the cytotoxicity test shows the sensor has lower cytotoxicity, and indicates that this sensor can be utilized for practical detection of trace cyanide in wastewater.

Synthesis and characterization of squaric acid based NIR dyes for their application towards dye-sensitized solar cells

Synthesis of novel cyan-colored sensitizing dyes bearing squaric acid core and 2,3,3-trimethyl-indole as terminal moieties has been conducted in order to fabricate dye-sensitized solar cells based on nanoporous TiO2. It has been found that position of -COOH functionality utilized for anchoring with TiO2 surface has a marked effect on solar cell performance. Carboxylic acid group directly substituted to indole ring gave about 5-fold higher conversion efficiency as compared to the dye when it was substituted in alkyl chain of the indole ring. Efficiency has been found to be hampered due to aggregation and enhancement in the efficiency was observed when dyes were used with chenodeoxycholic acid (CDCA). Using CDCA and long alkyl substituent at the N-position of indole ring to prevent aggregation and enhanced TiO2 surface passivation, respectively, has achieved a solar conversion efficiency of 3.15% with a short circuit current density of 7.26 mA/cm2, an open circuit voltage of 0.64 V and a fill factor of 0.68 for SQ-5 under standard AM 1.5 solar irradiation.

Visible Light Stimulated Bistable Photo-Switching in Defect Engineered Metal-Organic Frameworks

The incorporation of photoactive donor-acceptor Stenhouse adduct (DASA) moieties into Metal-Organic Frameworks (MOFs) provides a new route to the development of visible light switching materials. Herein, a DUT-5 mixed-linker defect series was exploited to produce a derivative group of DASA-modified materials via postsynthetic modification (PSM). The photoactive MOFs exhibited conversion stimulated by visible wavelengths and were stable following multiple cycles. Thermodynamic and metastable states persisted over an extended time period.

Ligand taking indocyanine green derivative as carrier as well as preparation method and application of ligand

The invention discloses a ligand taking an indocyanine green derivative as a carrier as well as a preparation method and application of the ligand. When the ligand is chelated with paramagnetic metal ions, an NIR/MRI multi-mode contrast agent is obtained, when the ligand is chelated with radioactive metal ions, an NIR/PET multi-mode contrast agent is obtained, and the obtained contrast agents can be used for diagnosis of various tumors, especially liver cancer. Meanwhile, the contrast agents are good in water solubility and low in toxicity, mutual verification of multiple contrast modes is achieved, diagnosis information is enriched, diagnosis precision is improved, and a feasible novel contrast agent is provided for early diagnosis of tumors clinically.